One Guy’s Idiot-proof Rules for Dressing

INTRODUCTION

This blog isn’t about telling people that they should be obsessed with clothes, that they should dress like a parade of corporate clones or that they can’t show their personality in their wardrobe choices.  In fact, far from it: it’s meant to be some words of advice from a fellow man on how you can tweak and upgrade your wardrobe without requiring a great deal of time or money (and, I also throw random, interesting stuff on here as well, such as biometric wallets, just for interest’s sake).  There’s not one way of looking good, and it always annoys me when websites and forums claim that there is – with that said, there are some things that I believe are mistakes that do guys no favours and I believe there are certain basic rules that will serve you well.

Occasionally I’ll check my inbox and find a message from someone about this blog, asking me either: a) to post more (thanks, I really do appreciate the encouragement, please keep it coming – I’ll try to post more); or, b) asking for some sort of general sartorial guidance.  This post is my attempt to kill two birds with one stone.  These are my general rules for dressing – some of them I’ve gleaned from various books, my father and grandfather, or other sources; some should be obvious and yet I see them gone wrong all the time; others are because I’m a bit nit-picky; and still others are just things that I’ve adopted and I’ve found to work well.  The common thread is that following these rules have helped to prevent me from at least looking like a jackass, which, as I’ve stated in the past, is one of the major goals of this blog.  I’m hoping this article will be something that I update and add to regularly, so feel free to send in suggestions and check back regularly (I’ll post on Twitter, @oneguysstyle, whenever I make a significant addition).

Without further ado, here are an assortment of rules that I follow to jackass-proof my wardrobe, along with my reasoning for them. I’ve also divided them into categories – things you absolutely have to get right, things that you probably should get right, and things that may take your style game up that extra notch.

THE BASICS – YOU NEED TO GET THESE RIGHT

1.  Fit is everything

It doesn’t matter what the label says;  how much you paid for it;  how much the retail price was; what store you bought it in.; or, what the “working for commission” sales associate said.  If it doesn’t fit (and cannot be made to fit), it’s not worth it.  That goes for suits, shirts, pants, jackets, belts or whatever else you can think of.  A Uniqlo shirt can look better on you than a Brunello Cucinelli shirt, simply because the former fits better than the latter.  Outside of Sweden, guys tend to wear clothes that are too big for them.  I’m 6’2″, 175lbs and grandmas and aunts have long sent me “Large” sized clothes.  In actuality I wear “medium” in most brands – use this as your benchmark.  Just because you’re over 6’0″ doesn’t make you a “Large” (although it may make you a “tall”, depending on the length of your arms and torso).  Wearing clothes that are too big for you make you look sloppy; and, contrary to common belief, they are no more comfortable than clothes that actually fit you.

The good news is, if you do have clothes that don’t fit (especially shirts) than a good tailor can likely work wonders (more about this in a minute).  I’ve had shirts that I’ve bought (knowing full well that I’d be taking them to my tailor) that I could almost make a second shirt out of with the excess fabric – the only thing that fit when I got them was the collar.  Don’t live your life trying to find ways to tuck in extra shirt fabric, or trying to keep pants from sliding down your ass, or looking like your jacket is wearing you rather than the other way around.  Either don’t buy clothes that fit like that in the first place, or, if  you already have, take them to a tailor.  Clothes that fit will make you look slimmer, taller, more professional, sexier and better proportioned.  There’s not attribute on that list that you don’t want.  It’s really as easy as figuring out what fits and buying it (or having things altered to fit) – but I constantly see men that have ignored this rule.  If you take nothing else from this list, at least understand the importance of Rule 1.  Check out the pictures above.  Clearly they represent something of a caricature, but it’s immediately clear to everyone when someone is wearing things that fit and when they’re not.

2.  Find a tailor and understand what he or she can and can’t do

People associate tailors almost entirely with suits.  This is like associating football entirely with quarterbacks – sure, they’re the most recognizable member of the team, but there are 50 other guys out there as well.  In the same way, to simply go to the tailor to have your suits fit is to barely skim the surface of their capabilities.  To whit, I recently purchased a polo shirt from a well-known manufacturer.  I have a few of their shirts already, all in a particular size (they don’t use the typical “small”, “medium”, “large” sizing).  I happened across a sale, was in a hurry and simply grabbed a shirt in what has always been my size and didn’t try it on.  Unbeknownest to me, this particular maker has introduced a new fit and their sizes are now a little bit different than before – which meant that I now own a polo shirt that swamps me, that I can’t return.   I took it to my tailor and,  $12 later, I have a polo shirt that fits perfectly and I was even able to customize certain details of the shirt.  At first this may seem ludicrous (tailoring a polo shirt? Really?).  However, think of it this way.  Before, I had an article of clothing that was essentially worthless to me – I couldn’t return it, and I would never wear it because it didn’t fit.  Now, I have a polo shirt that I will wear, and fits me perfectly – $12 very well spent, in my opinion, as it saved a $35 investment from becoming worthless.  Think of it this way: every pair of dress pants you buy needs to be tailored, just like every suit.  If a shirt doesn’t fit perfectly, it needs to be tailored.  I’ve tailored jeans that I liked, got a great deal on and wanted to keep, despite the fact that they didn’t quite fit (they now fit perfectly).  I’ve had my tailor repair jeans and shirts that had ripped, thereby reviving some of my favourite articles of clothing.  You can have ties narrowed, sleeves and armholes repositioned or narrowed, custom articles of clothing made, even t-shirts recut, sometimes for the price of buying you and a friend venti americanos and a muffin from Starbucks.  More importantly, they can take something you never wear, that lingers in the back of your closet like a spectre because you don’t like how it fits, what it looks like, or a certain thing about it and make it your “go-to” article of clothing.  Sometimes, you can go shopping in your own closet and find things that, with a little work, can be made new.

The only caveat is this: you need to know what a tailor can’t do.   They can’t really do much for suits that don’t fit in the shoulders (so, make sure your suits fit there; you can do some tailoring to the body of the suit, if need be).  They can’t remove shoulder pads, or reduce them.  They can’t really adjust the collar size of a shirt.  They can only work with the material you give them (i.e. you can’t have pants let out if there’s no material to let them out with.  You can’t have pants lenghtened without material being there to do it.).   It’s tough to adjust the rise of pants too substantially.  There is a limit to how many sizes they can take an article of clothing down (sorry, but those size 42 pants cannot be made into 32s…  The two back pockets will become one back pocket).  Sweaters aren’t really their speciality.  Re-working sleeves with functioning buttons is a problem (as it’s tough to move already made buttonholes without leaving very visible marks).  So is substantially lengthening or shortening a jacket (the pockets will now be in a slightly odd position, and it’s expensive).  Just like Superman had his limitations (kryptonite), so do tailors – in my experience, Superman is the most apt comparision for a great tailor.

3.  Wear a tie darker than your shirt, 95% of the time

– This is a good experiment:  walk into the suit section of Tip Top, Men’s Warehouse or other down-market men’s retailers – your eyes will be greeted with dress shirts in a ROY G. BIV assortment of colours.  Mannequins will be rocking solid black, red, green, dark purple and even orange dress shirts.  Then head over to one of the finer men’s stores in your area; I’ll toss out Harry Rosen, Niemen Marcus, Barney’s… any of those would be fine.  Now check out what colour shirts the mannequins and floor displays have on – I guarantee that at least 90% will be wearing shirts where the predominant colour is either white or blue (they may have red, purple, pink, green, orange or any other colour represented via stripes or checks, but the shirt will almost definitely be rooted in white or blue).  This isn’t an accident – solid black, red, orange, green and dark purple are not colours for dress shirts, unless you work as a magician in Vegas.  For whatever reason, it looks better when your tie is darker than your shirt, and these colours generally make this difficult.  They’re also tough colours to match and they’re definitely not traditional for business or just about any other form of social interaction.  This isn’t to say that you can’t wear solid shirts in colours other than white or blue; pink and lavender can be nice colours for shirts. However, stick with pale rather than dark shades, and pair with a tie in a colour darker than your shirt (navy, dark grey, etc). Furthermore, I have no problem if you’re going to cocktail party in a dark space at night and want to wear a black dress shirt with a black suit and no tie (see Bradley Cooper on the left).  If it’s nighttime and dark, and drinks are in the hands of many, then black may be an option (again, skip the tie) – but the look on the right is a train wreck.  Ties and black shirts do not go together, especially at the office.

4. Suit, shoes, tie and then shirt should be your focus in terms of allocating your attention and resources

A nice suit is something you need and is the most noticeable part of your business or formal wardrobe.  Plus, a suit is versatile, as it can be worn without a tie, just as a jacket with jeans or slacks, etc, or even the pants with a shirt and sweater.  Suits are also the most difficult thing to get right. Shoes are the next most important as bad shoes can destroy a look, even if you have a nice suit, tie and shirt.  Shoes can also be quite expensive and often demand a significant investment (although, if you purchase quality shoes, this investment should last a lifetime).  Ties come third as a nice tie will get you noticed positively, and a bad tie will immediately get you noticed negatively – if you’re diligent, you can often find nice ties at relatively low prices without sacrificing quality (eBay, Holt Renfrew Last Call, Saks Off 5th Avenue, Century 21, etc, can be excellent sources for high quality ties at bargain prices).  Furthermore, if you don’t own many suits, having a range of ties will make it seem like you have a wide ranging wardrobe.  Finally, shirts should be your last area of focus, as you can find nice shirts quite easily at good prices (see my articles about Shirts (here) and TM Lewin (here)).  The importance of shoes should really be underlined (I thought about putting them first).  Don’t fall into the trap of spending $150 on shoes and $140 on a shirt.  Spend $40 on a TM Lewin shirt, as per my post here, and $250 on the shoes (for some info about choosing shoes, read this post.

5. Don’t wear black suits or ties (or shirts) to work

Simply put, black is not traditional business wear, beyond shoes and belts.  A black suit doesn’t look good under artificial light (and is susceptible to, and looks worse after, fading more than any other colour).  Black ties are too formal for most workplaces (unless your job is hosting the Oscars, working at a funeral home or raising barns on the weekends with your Amish buddies).  And, as I discussed earlier, don’t even think about wearing a black dress shirt to any workplace.  Black is one of the hardest colours to match shirts and ties to.  Choose navy, charcoal grey, mid-grey, light grey, dark brown or even khaki or beige (in the summer time) for suits before you go with black.  This is especially important if you only have one or two suits, as your goal should be to maximize the number of colour combinations you can wear with your limited suit wardrobe.  That said, black is great when it comes to evening activities; for suits, ties or shirts.  So if you’re going out for a night on the town, as a 5th or 6th suit, or you’d like to wear it for other occasions that aren’t business related, think about black.  But unless you work as a chaplain or are going door to door for the Church of Jesus Christ of Latter Day Saints (or were given the suit as wardrobe for your role in ‘Book of Mormon’), go with navy or charcoal for your suits at the office, and skip black shirts and ties.

6.  Shoes polished.  Always.

When I was in university and needed a pair of brown dress shoes, I found a pair of Brown’s Shoe Store’s private label shoes on sale and bought them.  I couldn’t afford much more than a $75 investment and these looked nice enough for what they were and served me well.  Being that my grandfather and father have instilled in me a pseudo fanaticism about keeping shoes polished, I made sure that they sparkled when I wore them.  Amazingly, my $75 shoes got lots of compliments.  I’ve since upgraded my shoe collection, but nonetheless, these experiences underline something vitally important – you can make decent shoes look substantially better when you take the time to keep them polished.  I actually still have the shoes in my closet (the uppers remain in good shape, and, as they were glued, it was the soles that went first – I resoled them and they’re now my rainy day shoes). Conversely, you can make nice shoes look like cheap shoes if you do not polish them.   Polished shoes will set you apart from the rest of the dull-shoed masses and undoubtedly engender compliments.  How else can you upgrade your wardrobe for $3 (the price of a tin of shoe polish) and ten minutes of your time?

7.  The bottom button of a two or three-button suit should always be left undone.  The top button of a shirt worn without a tie should always be left undone too.

Not only is this the modern way of wearing suits, but, more importantly, suits are actually cut with the assumption that you will leave that button undone.  If you do it up, it will often result in a pull at that button and change the balance of the suit.  If you’re wearing a dress shirt (or casual button down, or polo shirt) without a tie, then leave the top button undone.  If you’re not wearing a tie, then clearly the occasion is at least mildly informal, so you don’t need to do that button up.  I realize that it’s hipster-chic to do these buttons up, but, at least in my mind, it doesn’t work for the majority of guys trying for this look.  If you want to add formality to your outfit, wear a jacket, don’t do it with that damn top button.  To my eyes, doing up the top button makes you look about as uptight as a nun in Vegas.  Even the guys on The Big Bang Theory don’t do up their top buttons, and that’s a strong statement.

8.  Step away from the cell phone belt holster

We get it, you have an iPhone, Galaxy or BlackBerry.  So do most 11 year old girls.  I’m sure you’re a very important man, who gets very important emails from very important people.  That’s great.  The good news is, those emails still manage to get to your phone when it’s in your pocket.  This applies in equal measure to your pants pocket and your suit jacket pocket – you really don’t need to display your BlackBerry like you’re Wyatt Earp in Tombstone.   I’ll make an occasional exception for individuals with holsters who wear suit jackets that will cover the holster, but grudgingly.  Unless you’re a time traveller from 5 years ago and are stuck with a BlackBerry with a side scroll wheel, than your phone will be slim enough to be in your pocket with no discomfort, I can assure you.  I covered this growing societal issue before here.

THINGS YOU SHOULD GET RIGHT

9. Polo or ‘golf” shirt sleeves should hit you mid-bicep, not below your elbow

One Guy’s Guide to Outlet Malls

I like nice things.  I also, at least try, to hold onto my familial frugality.   Buying something at full price has always been difficult for me – hence the full blown eBay addiction that occasionally rears its ugly head.  However, as much as I love the ‘Bay, it has one tremendous downside: the inability to physically see, touch and try-on what you’re purchasing.  Which brings me to the almighty Outlet Mall, the focus of this post.  Outlet malls (can sometimes) provide the bargains found on eBay and they also do not share eBay’s flaws noted above.  However, they have their own set of issues, which will be explored further below.  eBay is great in that it has an incredible selection of rare items AND it allows you browse these items while drinking a glass of wine in a bathrobe at home.  While some of the people you see at the typical outlet mall are only a half step removed from this, I would not recommend trying to mimic this experience.  If you want to visit your local outlet mall (if you have one), you will need to pry yourself off the couch to experience the joys (or, more often, horrors) that are part and parcel to such an expedition.  As someone who has been to many outlet malls on many occasions and has lived to tell the tale, please find some suggestions below that I hope will make your experience as good as digging through mountains of unsold goods in a crowd of people possibly can be.

1. Do not be specific

Almost daily, we hear the common refrain to “be specific”.  However, if you are looking for an oxblood suede belt with silver buckle, or a specific model of Tod’s loafers, or even just a “bathrobe”, and that is the primary purpose of your shopping expedition, than I would suggest not going to an outlet mall.  Outlet malls are places where you find things you aren’t looking for, but don’t find things that you are.  In other words, specificity is not the forte of  outlet malls.  From a time-cost persepective, you will spend eons of time trying to find that specific item you’re looking for.  Generally speaking, it’s not worth the time or trouble, particularly since outlet malls tend to be in the middle of nowhere.   Go to your preferred local store and spend a few extra dinero, or, easier still, troll eBay or Amazon.com in the comfort of your own home rather than sacrificing your day scouring sale bins at a distant outlet mall when your chances of success approximate the odds of the Cubs winning the World Series in the next twenty years (not out of the question, but history says that it’s highly unlikely).

2. Price, time and the sphere of availability

Walk into Harry Rosen, Bergdorf Goodman, Canali, Louis Boston, etc., and say that you would like a medium grey suit with pale blue pinstripes and they will likely have an array for you to choose from.  Same with the perfect yellow tie that you’re after, or the pair of brown boots you want for Fridays and the weekend.  It will be an easy, comfortable shopping experience (at least it should be).  When you reach the cashier with your purchases, you’ll see why: you pay for service and the ease and comfort described above.  Someone else is curating for you; sifting through the litany of options and providing you with precisely what you’re looking for with you barely having to lift a finger.

Outlet stores more closely resemble the following scenario: a dump truck pulls into the back of a warehouse and dumps a massive pile of loosely sorted apparel onto the floor for you to sift through with a crowd of fellow misers.  Much like Andy Dufresne, you will crawl through a pile of foulness to find the diamond in the rough.  This is part of the reason why they can offer goods so cheaply; they have stripped away much of the cost associated with good customer service.   I’ve made peace with this trade-off – just be prepared to spend quite a bit more time (and incur a substantially larger headache) per purchase than you normally would.  Furthermore, outlet malls bring clothes that would otherwise be out of your sphere of availability into that sphere of availability, which is the reason why it may be worth the trip.  That, plain and simple, is the value of outlet malls.

3. Reach for the top; ‘zig’ instead of ‘zag’

Further to “2” above, I have found the most success (and the best deals) when I’ve focused on items that I couldn’t otherwise afford, but have been made affordable at the outlet.  I cannot afford a $3,000 suit; however, a $3K suit marked down to $700?  That’s what you’d pay at SuitSupply or other mid-priced establishments.  In other words, you are getting a far nicer suit at a price that comfortably fits within your budget.

I believe that there are a few specific reasons as to why these situations present themselves and how best to capitalize on them.  The first is that people buy things that they know and recognize.  Simply put, most people recognize the names ‘Gap’, ‘ Hugo Boss’ and ‘Armani’, so items from these brands will not need to be as deeply discounted to sell, and will also be substantially more “picked over” due to their brand recognition.  Nearly everyone knows these names, but far, far fewer are familiar with Loro Piana, Pal Zileri, James Perse, Belstaff, Sundek, Grenson and even higher-end brands within a brand (eg. ’15 mil mil 15′ by Ermenegildo Zegna or Ralph Lauren Purple Label).  These brands make fantastic quality items that, at full retail, would constitute a huge splurge over other options for the majority of people, if they even knew what they were.  They may not sell at the retail store because, next to more recognizable names, people chose those recognizable names for the same price.  At an outlet store, they are suddenly deeply discounted because they were passed over, only to be passed over again for more recognizable brands, even at the outlet store, and therefore often discounted again.  I have, on several occasions after finding a gem gone to the retail store and asked for the brand, only to be told that they no longer carried it because it didn’t sell.  Undoubtedly, there are many that are familiar with these names, but far less than more common names, which gives you a better chance of scoring a great item at a great price from a brand that flies under the radar.  In addition, there are no ‘outlet brands’ for these particular marques.  Companies like J. Crew, Brooks Brothers, Hugo Boss, Calvin Klein, Burberry, etc., make items specifically for their outlets, meaning that the dress shirt you think you’re getting an outstanding deal on is actually not the same shirt they sell in their retail store.  I covered the idea of “outlet brands” in depth in the following post: https://onemansstyle.wordpress.com/2010/11/15/one-guys-daily-tip-beware-of-clothes-made-for-outlet-stores/

The best way to find deals at an outlet store is to be familiar with lesser known brands that make high quality items.  In other words, where everyone else “zigs”, you need to “zag” to find the best deals.

Here is a “cheat sheet” of brands I’ve seen in outlets which are not as well known to the casual consumer as Banana Republic, Hugo Boss, Burberry, Prada and the like, and often are deeply discounted because of it (if you’d like to learn more about the brand, click on the name as each is link to the respective brand’s homepage):  Loro Piana, Pal Zileri, Vince, Belstaff, James Perse, Grenson, Sundek, Rag & Bone, Billy Reid, Smythson, Aspesi, Charvet, Oxxford, Battistoni, Brunello Cucinelli, Turnbull & Asser, Samuelsohn, Drake’s, Nudie, Balenciaga, Mabitex, Incotex, Naked & Famous, WANT Les Essentials de la Vie, Jack Spade, Barbour, Martin Dingman and Kiton.

In other cases, many customers are unaware that a specfic brand has a variety of quality levels, leaving extremely expensive items available at deeply discounted prices.  Ralph Lauren Purple Label, Ralph Lauren Black Label, RЯL, Ermenegildo Zegna ’15 mil mil 15′, Salvatore Ferragamo Tramezza, Calvin Klein Collection, Gant by Michael Bastian, Gant Rugger, etc., can provide, as many do not realize, a much higher quality level than a brand’s standard fare.

While many of you will be aware of some, or even the majority of the names found above, keep in mind that many are not.  Furthermore, many that are do not frequent outlet malls.  This makes the Venn Diagram’s centre very small indeed.

4. Best and worst outlets

First, it must be said that many outlet malls are not even worth bothering with.  Sadly, my native country of Canada has embraced the concept of the outlet mall in much the same way as Americans have embraced the sport of curling: half-hearted at best.  In Canada there are really two places worth visiting: Holt Renfrew Last Call (which, I believe, is only in Toronto now), and Harry Rosen Outlet (again, only in Toronto).  Basically, if you’re not in Toronto, you’re probably out of luck, at least locally.   If, however, you reside in, or near the United States, there are a number of great outlet malls potentially close by.  This is particularly the case if you live in an area frequented by tourists: New York, Los Angeles, Miami/Fort Lauderdale, Niagara Falls, San Diego, Las Vegas or Phoenix.  Therefore, the first decision to make is whether it’s even worth driving out to the nearby outlet mall.  In many cases, it may not be worth it at all.

I’ve found the majority of my best deals at department store outlets.  Barney’s New York, Century 21, Niemen Marcus Last Call, Holt Renfrew Last Call (apparently there is a shortage of outlet store names, as somehow two share the same one) and Saks Off 5th tend to be some of the best.  Unfortunately, like every other store at the outlet mall, the value of these stores has been decreasing.  Formerly, they were the exlusive domain of unsold merchandise from their regular stores; however, lately they have begun to sell “outlet store merchandise” – clothing manufactured expressly for outlets (usually, they are named after the store itself, eg. Saks Fifth Avenue Green).  Nonetheless, these stores are still the cream of the outlet crop in terms of bargains, as there remains loads of items that went unsold at retail locaitons, providing some excellent access to nice things at good prices.

In addition, some of these stores, offer customer loyalty programs that provide even deeper discounts on items if you show the card associated with the program, or offer discounts if you sign up for a credit card.

The outlet stores I would tend to avoid are those that almost exclusively sell merchandise manufactured for outlet malls: Brooks Brothers, J. Crew, Banana Republic, Calvin Klein, etc.  By and large, the prices match the quality of the items being sold.

5. Buy with purpose, not for price

You may think that the teal blazer is kind of cool and it’s down from $722.98 to $89.99!  How could you lose on this deal?  Well, after it sits in your closet, unworn, for 2 years, the economics no longer support this particular purchase.  Don’t buy something cheap, buy something because you know it will be part of your regular rotation, or you have a specific purpose in mind for it (wedding coming up, been looking for an orange tie, you can never have too many socks…).  It’s cheap and you may not have otherwise been able to afford it (“I’ve always wanted an Hermes tie… it’s just too bad it’s pink, yellow and orange, with pictures of bunnies on it…”), but that doesn’t make it a wise purchase.  I have a number of items I’ve bought at outlet malls that I wear/use all of the time (my go-to carry-on bag, a number of my favourite ties, some favourite shirts, one of my favourite suits) but I’ve also had a few losers haunt my closet after the fact.  You really need to win much more than you lose, otherwise you are negating the savings you believe you are getting via outlet shopping.  Only buy something at an outlet mall if you’d buy it in a regular store.  More is not always better when it comes to a wardrobe; I find that I gravitate towards certain items time and time again, and the remainder simply take up precious storage space in my condo.  Buy like a surgeon, not a drunken gambler.

6. Get in, get out

Outlet mall trips are like commando raids – you want to get in and get out as quickly as efficiently as possible.  The decending hordes typically do not get there until mid-afternoon.  Be smart and go first thing in the morning.  You do not need to into every store and wander around.  Only go into the ones that you actually may make a purchase in.  Do you really need to wait in line to get into the Coach Store?  (Hold on – you WANT to get into the Coach store….?  Your problems are bigger than I thought….)  Outlet malls are exhausting places; don’t blow your stamina at places that are a waste of your time.  If you’re there with your wife, girlfriend or friends, and your attention is starting to wane, often times there are restaurants with bars to grab a bite to eat and a drink (often times at very cheap prices – they want you to stay as long as possible, not to go elsewhere to find something to eat) when you’ve just about had enough.

Oneguysstyle’s Inaugural Christmas List

We’re getting closer and closer to my favourite time of the year.  In the spirit of the season, here’s what I’m hoping to find under the tree this year:

1.  Tumi Alpha Frequent Traveler Zippered Expandable Carry-On Bag

I’ve been doing a fair amount of traveling this year, which is something I very much want to continue into the future.  While I make do with a myriad of beat-up and abused luggage, this rolling carry-on is what I really want.  Made of Tumi’s signature ballistic nylon, it’s damn near un-damageable.  I also love the removable garment sleeve, which holds up to three suits and would allow me to not have lug around a separate garment bag.  Airports are places to survive, not enjoy, and so the more your rolling suitcase allows you not to carry, the better.  I’ll have mine in black, with the complimentary monogramming (so I can tell it apart from the herd of Tumi’s seen at every airport), please.  Check out this particular suitcase here; it’s available for $595.  They also regularly find their way to eBay.

2. Alexander McQueen Silk Skull Print Scarf

Because why not quietly feel like a bit of a badass this year?  In a muted navy (and with a small pattern that looks quite conservative unless you get quite close to it), it’s a fantastic way to be daringly conservative, if there is such a concept.  Alexander McQueen produces items that are kind of a cross between James Bond and Keith Richards and really, are there two cooler male characters than them?  I’ll have mine in navy with white, as conservative as possible to off-set the pattern.  Alexander McQueen’s website is alexandermcqueen.com but I would recommend trolling eBay for better prices.

3.  Gant by Michael Bastian Oxford Shirt

My vote for the coolest collaboration of the year.  Michael Bastian makes some of the finest “american style” menswear in the world.  Think of a modern interpretation of what the Kennedy brothers wore in the ’60’s.  He prides himself on making the finest examples of classic American items like khaki pants and shorts and oxford shirts with modern fits.  The downside is that the “finest” carry a price to match.  Which makes his contribution to Gant absolutely perfect.  Gant has long been something of a poor man’s Polo Ralph Lauren.  Their collaboration with Bastian has bumped up their price a bit (but not really very much at all considering) while delivering some of the best items you’ll find on the racks this year.  I would recommend going with what Bastian does best – the oxfords, the khakis and the corduroy pants.  Given that I wear the hell out of white oxford button-down I already own, a pale blue oxford button collar shirt tops my list.  Check out the Michael Bastian collection at Gant’s U.S. website here, the oxford shirt I’m talking about here, or in stores in Canada at Harry Rosen for a little over $150.

4.  Playful socks from Paul Smith, Richard James, Smart Turnout or Happy Socks

I’m a bit sick of the drab socks in my closet, particularly as drabness of winter has set in.  Which means that I’m looking for some interesting and colourful options in my sock drawer.  Any of the above makers will do (I’ve arranged them from highest to lowest in price), preferably with a some red in there somewhere.  More info can be had at paulsmith.co.uk, richardjames.co.uk, smartturnout.com or happysocks.com.

5. Slim fit Sea Island Cotton Shirt from Charles Tyrwhitt

We’ve covered the fine Sea Island cotton shirts made by Charles Tyrwhitt before (see here).  I’m going to be heading somewhere warm after Christmas, so I’d like a shirt that’ll keep me comfortable and cool when I go out for dinner.  Anything with a pattern in blue or pink will do quite nicely.  Also, skip the french cuffs and opt for standard barrel cuffs – I’m inevitably going to forget to  pack cufflinks and the less you need to bring  on vacation, the better.  Check out ctshirts.com for more details.  Shirts from around £59.95

 

 

6.  Belstaff Roadmaster jacket

From the black waxed cotton exterior and traditional tartan interior, to the slim fit and belt, there is no cooler jacket than this one.  Made for motorcyclists by Belstaff, a company founded in England in 1924, it not only keeps you warm, but it’s rugged waxed cotton feature keeps you dry.  You may remember seeing Will Smith in one of these throughout the film I am Legend.  Instead of following the herd and buying a leather jacket, buy one of these classics and instantly look about as cool as a man can look.  Mine would be in black, but the olive and brown also look great.  Available via jcrew.com, belstaff.com and a variety of other places, for around $595.

 

 

7.  H&M Tweed Blazer

Winter = tweed.  It keeps you warm and stylish through the months of cold we experience in Canada and in the northern U.S.  Plus, it’s timeless and will never go out of style (even if it does, at H&M prices that isn’t too big a fear).  Add on some elbow patches and you’ve really got a winner.  H&M offers a modern fit, which makes sure you don’t look like your Grandpa or your first year English professor.  Grey is the way to go, at least in my opinion.  Check it out in H&M stores for around $130.

 

 

8.  The Art of Shaving Sandalwood Shaving Cream

Shaving is the cross that every man bears, so why not make it tolerable (or perhaps even enjoyable) with some quality shaving cream.  Once you lather this up with a badger brush (feel free to skip the one from Art of Shaving and pick one up from the drug store), you’ll realize you’ve been missing out with the thin crap you get out of a can.  Plus, the sandalwood smells great, so you can skip the aftershave.  There are other scents available, but I would skip the lemon as I’ve heard it can adversely effect certain people’s skin.  The $22 price may seem expensive for shaving cream, but my tub has lasted me more than a year (you’ll plow through a few cans of Edge or Gillette in that time period), so it’s actually not as expensive as it seems.  Time for a replacement tub for me.  More info available at theartofshaving.com.

 

 

9.  James Perse Brush Stroke Crewneck

James Perse very well may make the world’s most comfortable casual clothes.  I’ve already got a long-sleeve graphic t-shirt that I wear all the time from JP, but I think it’s time to add to my collection.  This example is made from heavier “slub pique” cotton, which combines a bit of extra thickness for winter with Perse’s famed softness to equal the most stylish way to laze around on a Sunday.  Available in black, grey and white, I think I’m partial to the grey.  James Perse is available at jamesperse.com or in Holt Renfrew, Niemen Marcus and other such retailers.  This particular shirt is available for $135.

 

10. J. Press for Urban Outfitters Drill Pant

J. Press sells preppy like nobody else.  Urban Outfitters does the same for trendy urbanwear.  Mix the two together and you’ve got classic items with a modern look.  J. Press was founded in 1902 in New Haven, Conn., which many may know is also the location of Yale University.  J. Press’ other stores are in Cambridge, Mass. (home of Harvard), Washington, D.C. (home of Capitol Hill and Georgetown University) and the inevitable store in New York City.  J. Press’ ties to the Ivy League schools and their distinctive preppy dress code is long-standing tradition.  The one issue has been that they’re frankly a bit stuffy and out-dated in terms of fit.  Enter Urban Outfitters, which fills the exact opposite end of the spectrum, while still catering to the same audience.  A match made in heaven, and these heavy duty khakis are the pick of the litter in my mind (see my earlier post on slim fit khakis: ).  The slim fit and cool details such as the buckle cinch at the back make them instant classics.  Check out the whole J. Press x Urban Outfitters collection at www.urbanoutfitters.com or in stores.  These pants are $78.