15 Classic clothing pieces every guy should own


Special to Squawkfox: This article is by Carl. He’s a guy. Kerry (not a guy) tried to write about men’s fashion, but she sounded too much like a crazy ex-girlfriend. Since Carl has more experience with wearing men’s pants, he snagged a spot on Squawkfox. Enjoy!

When Kerry posted her list of 12 Classic clothing pieces every gal should own, I was intrigued. Only 12? If women’s clothing can be defined by 12 key pieces, where does that leave me as a guy? Would the same kind of scrutiny leave my closet deconstructed to only three essentials, including underwear?

I decided to go through my closet, and was surprised.

Once I looked past the free promotional t-shirts from software companies, I found my wardrobe also contained a number of quality items that have stood the test of time.

Here’s why every guy should stock quality, classic clothing pieces:

It makes life easy. Like most guys, I’m lazy. Having a few versatile items makes getting dressed and looking good (relatively) straight forward. Good shirt. Nice pants. Done.

Good stuff lasts. I hate clothes shopping. When I buy quality, timeless items my clothing lasts, and as a bonus I need to make fewer trips to the mall. Unless you end up wearing your good jeans while making firewood, in which case you probably deserve what you’re about to get — multiple shopping trips and an annoyed spouse.

Chicks dig it. (Kerry says: “maybe”.) Any woman is going to have a hard time seeing your charming personality if she needs to look past the fact you’re dressed like a slob. And on the other end of the spectrum, if you look like you’ll need more closet space than she does, that’s not good either – every house has a finite number of closets. The sweet spot between these extremes is where you want to be.

It’s your job? Well, it helps your job. Dressing snappy at the office or for your job interview can help keep your career moving. According to a recent CareerBuilder survey, you’re more likely to get the job or promotion over the next equally-qualified guy if you’re dressed better. And with a few essential clothing pieces, you don’t have to spend half your salary doing it.

So what are the essential guy clothing pieces? Unlike Kerry’s dirty dozen, here are the fifteen classic clothing pieces every guy should own:

1. The classic suit.

Unless you’re a lawyer, a banker, or in some other unfortunate profession where you need to wear a suit every day, one suit should last you a long time. Tie styles may change from year to year, but a classic suit should last you decades if you stick to a simple black or dark gray. A classic suit can be worn as a formal look for weddings, funerals, and job interviews — just hopefully not all in the same day. Or to mix up a casual look, wear the suit jacket with a pair of jeans.


Since a suit is probably one of the most expensive articles of clothing you’ll ever own, it’s worth looking around for a deal on a high quality item. Many independent stores will sell suits from smaller labels that are just as good as the big brands, only for a lot less. Or if you’re adventurous, do what a former colleague of mine did. On his trip around the world, he spent a month in Hong Kong. A local tailor made him a custom suit for less than one-tenth what it would have cost him at home. Not for everyone, but it’s a great looking suit.

2. Collared dress shirts.

Get one in white for a formal look with the suit, and get a bunch in fun colors and patterns. I used to play this safe with variations of ‘the blue shirt’, but you really only live once.

pink shirt

A nice pink dress shirt can look great (and very manly), both with a suit or a pair of jeans — that’s two outfits for the price of one. Just make sure your shirt is ironed! Yes, real men wear pink.

3. Black leather shoes.

Whether you’re on the job or on a first date, the shoes you wear can significantly affect how other people view you. Even the sciency geeks (like me) agree that shoes can be a source of first impressions. And for many situations, a good pair of black leather shoes are a must. While boring banker brogues will do in a pinch, there are plenty of more interesting black leathers you can wear.

Fluevog James

My simple black Fluevogs look great with both the suit and with jeans. Kerry even claims she’s seen other women ‘check them out’. I think she’s just being nice. If you buy a quality pair of leather shoes that can be resoled, they’ll easily outlast any other article of clothing you own.

4. A nice watch.

Like your shoes, your watch can define what others think of you. Nothing is going to clash worse than wearing a black plastic digital sports watch with a nice outfit (other than wearing running shoes with your suit, but that’s just wrong). A simple stainless steel analog watch will go with pretty much anything, and will hopefully tell you the correct time too.

seiko watch

While some Swiss-made watches can cost as much as a car, this Seiko Men’s Stainless Steel Kinetic Watch is just $120 — a deal considering mine was around $400, and is still ticking happily over a decade later.

5. Merino Sweaters.

The reason I own a bunch of merino sweaters is because they’re warm and comfortable, and sitting near an air conditioning vent all day sucks. But what I soon found out is that these sweaters are incredibly versatile. Dress them up by wearing a crisp collared shirt underneath, or stay casual with a simple t-shirt. And as the temperature changes throughout the day, you can easily lose a layer and still look good.

merino sweater

Ok, the real reason I own a lot of these sweaters is because they happened to be on sale in Banana Republic the one day I dared to venture in. At $18 a sweater, I bought five of them, one in each colour. Saving money and not having to go shopping for sweaters again for a very long time is a win-win in my books.

6. Good jeans.

Jeans are the casual staple of any wardrobe. They can be dressed up with a nice buttoned shirt, or worn casually with a t-shirt.

blue jeans

A nice dark wash will go with pretty much anything, so the most important thing really is fit. For the longest time, I would buy jeans that were a bit too short; they’d fit nice in the fitting room when I wasn’t wearing shoes, but when I went to wear them at home, it looked like I was preparing for a flood. Kerry helped me onto dry land with this one, and now my jeans fit like they should.

7. Khakis, Chinos.

Without going into the details of fabric and styling (which I really don’t understand all that well), I’m going to call these khakis or chino things comfortable pants in a beige fabric that aren’t jeans.


A nice pair of light khakis can be really comfortable, especially in the summer. With a blue dress shirt, khakis can be formal enough for a job interview (at least, at a software company), or with a light linen shirt, you can be sipping margaritas on the patio. Apparently these types of pants are still available with a pleated front. While my dad buys them like that, you shouldn’t.

8. A belt.

You need something to keep your pants up. Get a black one and a brown one, or a reversible leather belt for under $20. Wear the color that matches your shoes. It doesn’t get easier than that. A simple silver-colored buckle is best here too – unless you live in certain geographic regions, you’ll probably want to avoid big buckles with cattle on them (you know who you are).

leather belt

Since belts are freakishly expensive for what they are (a straight piece of leather with holes), you really shouldn’t pay full price for one. I picked up a casual canvas belt at Gap on sale for $5 last year, and all my leather belts have come from Winner’s — a big chain of stores selling discount clothing.

9. Casual shoes.

This really could be almost anything, depending on how casual you are. A fun pair of Fluevogs works for me, but a good casual shoe can be anything stylish from canvas to leather. The only way you can go too casual is by wearing running shoes or hiking boots — unless you’re anticipating a quick escape in the mountains, that look is kind of dorky.

Fluevog Angels

My colorful leather ‘Vogs cost around $200 after tax but have lasted several years of near-daily wear. Since the uppers seem indestructible, I’ll be getting them resoled when the rubber wears out in a few more years. I figure when I’m done with them, I’ll have spent a lot less than I would have, even if I’d only bought a pair of cheap Converse each year.

10. Polo shirts.

Not to be confused with its senile cousin the golf shirt, a polo shirt combines the comfort of a t-shirt with the dressiness of a collar and a few buttons. If you’re wearing a polo shirt, you can be comfortable lounging at the beach, and still be dressed appropriate enough to chat with your boss when you run into him while buying beer after both of you ducked out early on a Friday afternoon.

icebreaker polo

Don’t pay the premium for ones with embroidered emblems of polo players, alligators, or magic flying unicorns. I have a few simple cotton polos, but my favourite is the Icebreaker SuperFine 200 Stripe Kent Polo Shirt for under $55 — I own two.

11. T-shirts.

T-shirts are the most casual essential on my list. A plain solid color is the simplest, but a print with your favorite band that nobody’s ever heard of can be a part of your personal expression.

gray tshirt

php tshirt

My only thought on t-shirts: Only wear ones you’ve actually paid for. Wearing a freebee shirt — whether it’s from a beer garden or a programming conference you just attended — just looks lame.

12. A Warm Pea Coat.

Winter is coming. When it gets cold out, you can wear a puffy ski jacket that makes you look like you were attacked and eaten by a sleeping bag, or you can wear a wool pea coat that is both warm and still stylish.

wool blend peacoat

While a good wool coat is usually pretty expensive, they often go on sale in the spring. This BGSD Men’s Wool Blend Pea Coat in Black or Charcoal is just $119.99, and the reviews are wicked.

13. Scarf.

Not just for Europeans, scarves can keep anyone warm on a blustery day.

merino scarf

Wrap it around your neck before you put your coat on, and it’ll keep you warm up to your ears while no gust of wind will make it down your back. Scarves can be made of pretty much any material, but I like a non-itchy merino wool scarf. I got mine on sale for $5, again in early spring.

14. A Murse.

Are you man-enough for a Murse? Get your masculine on with a man-purse, a fancy name for a small messenger bag. There are plenty of nice leather ones, but I’ve got a black synthetic one from The North Face. What goes in my manly Murse? My iPad, a camera, a Swiss Army Knife, and a lightweight tape measure. No guy should ever be without a tape measure… especially at Ikea.


I picked mine up for 40€ in Berlin last fall. With my iPad and camera securely stowed, I was able to relax while traveling around Europe, knowing no valuables were left behind in hotel rooms. Back in North American the Timbuk2 Freestyle Messenger Bag sells for around $70 and will last you many commuting or world-wide trips.

15. Leather wallet.

While plastic wallets, and even homemade wallets out of duct tape are cool if you’re in high school, every guy should have a slimfold leather wallet. Black or brown, either color will go well with pretty much any outfit — although, hopefully you’re not needing to pull it out so often that it becomes a *noticeable* part of your outfit.

leather wallet

Keep it sleek by avoiding ones with change purses, and only keep a limited number of cards in it. And purge any receipts you’ve collected daily – you don’t want to end up like George Costanza.

Thanks for reading my first post. Hopefully my European fashion sense won’t scare too many of the ‘squawk’ dudes away.



  1. SavingMentor September 29, 2012 at 11:54 am

    Geez Kerry you made it sound like this article was a disaster waiting to happen on Twitter. I think Carl did a fine job. Simple fashion advice with great pictures!

  2. Kerry September 29, 2012 at 11:58 am

    @SavingMentor LOL! What can I say, but 140chars makes writing about my husband’s writing hard. 🙂

  3. Deb September 29, 2012 at 12:07 pm

    Nice job Carl. Being a single Mum of a young man sometime I just don’t what to tell him about certain things. He did figure out shaving, dressing on the other hand. What guy wants to take fashion advice from his Mum? I think this piese will be very helpful for him. Thanks.

  4. Lisa September 29, 2012 at 12:15 pm

    The Carl did great. Not only that, but a tailored suit at one tenth the cost of home, now makes a trip to Hong Kong easier to justify. 😊

  5. Rich September 29, 2012 at 12:23 pm

    Interesting that with both a classic suit(I get mine from Jos.F Bank in the tree piece version)and collared shirts there is no mention of neckties which are de rigeur when wearing a suit in a formal setting. I prefer the classic wingtip or a Scotch grain leather plain toe for wear with a suit. Penny loafers are the classic casual shoe but a plain toe lace shoe are some mens preference. For a winter coat my preference runs to a trench coat style with a removable lining. Last item is a plain fedora for winter wear but an Indiana Jones one is more versatile.

  6. Tara September 29, 2012 at 12:26 pm

    Well done Carl! Great advice that I have been urging on my husband for years, but the only problem is he’s a plus sized guy. There really isn’t any way to be economical unless I want him wandering around town in sweatpants and a t shirt like Captain sweatpants (the big bang theory).

  7. Sherry September 29, 2012 at 12:41 pm

    Ditto, what Deb said. Grandfathers and Uncles are fine for shaving and hygiene advice but dressing? whoa, love them but wouldn’t want to look like them. Great article, Carl.

  8. Madelyn September 29, 2012 at 1:29 pm

    This is a great article! Nice work Carl! I will definitely use this info to help my hubby. Right now he has a closet and drawers overflowing with beat up stuff from decades ago. To give you some perspective he brags about still wearing a shirt he got when he was 21 and he’s 39! Now we can just get a few classic pieces to replace all the junk! Thanks!!

  9. Alison September 29, 2012 at 2:41 pm

    Great article! I agree with all points, except the murse. A briefcase will have to do. Now, how can I get rid of the Iron Maiden T-shirts without him knowing?

  10. Echo September 29, 2012 at 2:47 pm

    Nice post, Carl. I found it challenging when I moved from a job where I wore a suit and tie every day to a more casual job in sports marketing.

    I still can’t help wearing a collared dress shirt and tie on occasion, even when my colleagues are in jeans and a golf shirt.

  11. YOY September 29, 2012 at 5:53 pm

    May I suggest ye old jcpenney big and tall for nice items at reasonable price .. My MIL always made her tough cookie husband wear pink shirts because it made him act nicer ! LOL

  12. Brenda September 29, 2012 at 7:32 pm

    Great info, Carl, thanks Kerry, for lending him to us! 😀

    I’ll have to put this to good use with my hubby, whose idea of going out dancing is jeans and runners. ugh

  13. Simon September 30, 2012 at 5:57 am

    Glad I voted yes. Good article – easy to read and well written.

  14. Iva September 30, 2012 at 6:01 am

    Great article. Thanks for the fashion advice. I read it to my husband and we agree that about 10 of those items are a must-have for his wardrobe. (The cold-weather items are needed in the south).

  15. My Own Advisor September 30, 2012 at 10:36 am

    Nice post Carl!

  16. Steve September 30, 2012 at 11:13 am

    Well I do love Carl but I will be lone voice of dissent. Expected specifics, not generalities. Of course I need a belt. Of course I need t-shirts. What else am I gonna wear? The exception was mentioning the Merino sweaters. That’s good and specific. Wear THAT sweater over other sweaters. Similar should have been “close fitting, tight knit t-shirts” (they look better than the ones with flappy arms and are much softer against skin. Don’t get me wrong, ain’t being an asshole, just a gentle opinion from gentle me. 🙂

  17. Riscario Insider September 30, 2012 at 11:35 am

    Fifteen items is a lot but Carl covers business and casual.

    I was at a fashion event for Bay Street lawyers in Toronto a couple of weeks ago. There was an emphasis on having pocket squares (I’ve got none) and brown shoes (recently bought a pair).

    Where do men go wrong in a business environment? The murse. It’s important to have a nice bag. No backpacks. No blatant logos. I use a dark brown leather bag for “real” meetings and a black nylon bag if I might need to put it on the floor (say at a coffee shop). I got both at Costco years ago.

    If a watch is clothing, then so is a pen. Having a nice- looking pen makes an impression. I like Sensa because they’re easy to hold and reasonably priced.

    PS There’s no mention of underwear, socks or ties 🙂

  18. Kerry September 30, 2012 at 11:42 am

    @Riscario Insider “PS There’s no mention of underwear, socks or ties :)”
    Did I mention that Carl is European? 😐

  19. Khai September 30, 2012 at 1:02 pm

    I’ve been carrying a man purse and wearing pink shirts for well over a decade and a half. What’s *new* to me however, is the revelation that are “European fitted” shirts. There are your typical North American cut dress shirts, which are akin to wearing a nicely patterned tent. Then there are your “fitted” North American shirts, which are more like wearing a bivvy bag. An European “fitted” shirt however, is truly a revelation! If I had known this back when I worked in the finance sector I wouldn’t have a closet full of very nice, but extremely baggy dress shirts that need to be “tucked & wrapped” (or hidden with a vest – a sweet trick). I’m not so certain that I’m fully on board with the European fitted chinos, however…

  20. jennyp October 1, 2012 at 11:44 am

    I adore that both this and the women’s article support and encourage the purchase of Fluevogs! I’ve had my eye on a couple of styles for several years, but couldn’t justify the price. Now I have a couple more bullets in my gun when I say that they are a *practical* purchase for comfortable daily office wear once I graduate from college in April. Thanks to both of you 🙂

  21. Kerry October 1, 2012 at 1:02 pm

    @jennyp Busted on the vogs. But as far as quality resoleable leather shoes go — I can’t fault Fluevog for making kicks that last, and have soul. 😐

  22. Rob October 3, 2012 at 6:57 am

    Excellent article. Curious that it’s mostly women commenting on it.

    I’ve been considering expanding my wardrobe slightly beyond jeans, shorts, t-shirts, Tevas and running shoes so this article is timely.

    Not to detract from Carl’s posting at all, but people further interested in this topic (or people scared by Carl’s European-centric style sense) could look at the website “The Art of Manliness”. It’s male-centric but could equally well be “The Art of being a human”. Which would be a less interesting title. I won’t post the URL here. You all know how to use google.

  23. Kerry October 3, 2012 at 2:22 pm

    @Rob My inbox is bursting from men emailing me about this post. Not sure why. OK, they didn’t like Carl’s shoes. 🙂 Artofmanliness.com should get the manly men there. Great site!

  24. Rob October 3, 2012 at 2:55 pm

    @Kerry: Glad you like it. I figured if you wanted a link to a “competing” blog you’d put it in.

    I wasn’t so sure about the shoes either, but the *concept* of a pair of nice shoes and some daily-ware shoes is a good one.

  25. Preet October 3, 2012 at 3:54 pm

    I can’t do the murse. Sorry.

    And you forgot longjohns. Tucked into the socks. Starting in October. Or is that just a “me” thing? 😛

  26. Tim Stobbs October 4, 2012 at 6:19 am

    @Kerry – I don’t know why you worried this was a good post.

    Overall I agree with the majority of the advice, even if I don’t own a few of the items like the murse. Sorry most of the time I do just fine with my pockets and if I really need to carry some larger items I take the ever useful backpack. I can’t justify getting a ‘nice’ looking bag for a handful of times this comes up for business meetings.

    Perhaps I’ll offer one other tip: no one cares what you look like outside at -40C windchills. We are all dressed up like puff balls trying to stay warm. (From the guy that lives in Regina, SK). I personally invest in layer coats so I can slowly add on as the temperature drops.


  27. Rob October 4, 2012 at 2:49 pm

    @Riscario Insider:

    Seriously? A PEN? This is the 21st century. Who uses pens any more, other than to scribble a signature on a credit card slip?

    Now, a nice shiny (indestructible) watch like my Beitling Aerospace.. that’s “clothing”… 🙂

  28. Rob October 4, 2012 at 4:17 pm

    Man….the bowling shoes are just plain WRONG!

  29. […] 15 Classic Clothing Pieces every Guy Should Own […]

  30. Mike October 14, 2012 at 2:22 pm

    Oh man, I gotta get me a peacoat. Other than that I’m reasonably stocked up on everything else on this list.

  31. Chris November 29, 2012 at 9:08 am

    Why do chicks carry such large bags? Because they end up holding their partner’s wallet, phone, keys, other things in pockets. Love the styling looking man purses …yikes sorry murse…think of it as a small briefcase in case your Canadian male ego is getting tangled up with the word purse.

  32. Greg May 8, 2013 at 8:03 am

    @Mike Love the peacoat as well, the ability to dress up your appearance instantly, even with a T-Shirt underneath!

    @Carl Great article, my only comment would be the khakis, I wouldn’t wear that to any interview! While I agree that you can definitely come across as professional in it, unfortunately most people correlate khaki as casual, which may or may not be the impression you want to convey.

    Great article!

  33. Greg February 9, 2014 at 7:27 am

    I am shocked.
    1. Dude, black is the worst choice for a suit color. Pick dark blue or grey.
    2. The black shoes that you posted under number 3 are totally unsuitable to be worn with a suit.
    “First impression”? – Oh yes – a garbage man.
    This is how a shoe that is to be worn with a suit looks like:

  34. Robin April 17, 2014 at 1:27 pm

    Regarding trips to Hong Kong for suits. There are many “Travelling Tailors” who do circuits from city to city taking measurements for suits that are made in Hong Kong and then shipped to the buyer. When they arrive there is usually a local tailor that does the final fitting as part of the cost of the suit. Essentially a custom tailored suit form about the cost of a good off-the-rack. Classic grey or dark blue are your best colour choices.

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