Suits with Sneakers

April 10th, 2011

The other day I received an interesting, thought-provoking, question from a reader: if you could only wear one outfit for the rest of your days, what would it be?

After giving it some thought, I decided that it would have to be a suit with sneakers. It’s the ultimate go-anywhere, always-appropriate (or perhaps ‘never inappropriate’) outfit.

A look similar to these would work for just about any occasion you could imagine (date, class, business meeting, dinner, sporting event, church, brunch, traveling, bar, museum, wedding, movies, family get-together, bike ride, night club, concert, shopping, to the gym, opera, walk in the park”¦you name it). There is virtually no situation where you would be completely out-of-place wearing a (correctly styled) suit with sneakers.

Here, 3 examples to go from day to night, to anywhere and back.

1. Whites Middies


This olive cotton suit, now part of my first Ready-to-Wear collection (with a few minor tweaks) releasing later this Spring, has been getting tons of wear (as you can see, it could use a press). It just works with everything, from casual to dressy. Also, the more I wear it, the more unique (but still wearable) I realize it is. Guys just don’t wear olive suits, it’s a shame.

Pair it with a neutral henley and a hoody in an accent color and you have a comfortable, style-forward outfit that a wide variety of people can appreciate.

Just don’t step on my fresh whites!

Bonus Tip: This fabric is 98% cotton, 2% Lycra (for stretch). This tiny amount of stretch makes all the difference in the world from a comfort and mobility perspective. I’ve actually put this thing to the test and played a brief street basketball game in it. Admittedly I didn’t take (or make) many jumpshots, but was able to take it to the rack just fine :)


Olive Worsted Suit

  • Burgundy full zip hoody by Cheap Monday ·
  • Beige henley by Ralph Lauren Polo ·
  • White sneakers by Nike ·
  • Linen paisley pocket square Vintage ·
  • Tortoise shades by Persol ·
  • Watch by Montblanc Timewalker Automatic
  • · Olive cotton suit

2. Sleek Low Tops


This outfit is so simple and easy, but so effective. It doesn’t take much longer to throw this on than the same old t-shirt & jeans – but the image upgrade is night and day.

As my girlfriend confirmed, this is a great look for dating and going out. It’s polished and put-together but still approachable and laid back. Because you don’t want to be the intimidating “works too hard” guy who wears a full business suit and tie to the bar/club, but you also don’t want to be the sloppy “doesn’t work hard enough” (or “doesn’t make enough money”, hah) guy in a t-shirt and baseball cap. An outfit like this strikes the perfect balance between successful and cool, making it “very attractive to the opposite sex”.

Bonus Tip: With a jacket you don’t want to roll the sleeves since they are usually lined (if they are unlined, go for it), rather you want to push them up the forearm over the elbow. If the sleeve is well tapered (which it should be, if not you can have it taken-in) it should keep itself up around the bicep.


Donegal Tweed Suit in Monochrome

  • Black cotton/linen v-neck t-shirt by Kenneth Cole ·
  • Black sneakers by Vans ·
  • Tortoise shades by Matsuda Eyewear ·
  • Watch by Montblanc Timewalker Automatic
  • · Grey donegal suit

3. Classic Converse


Of course it’s okay to recycle outfits, as long as enough time has passed or you’re with a different crew of people. I’m not too cool to admit that sometimes, when I’m feeling lazy (or I really like a particular outfit), I will wear it on back-to-back days or nights, as long as it didn’t get dirty and I don’t anticipate seeing any of the same friends  ;) shhhh”¦

If you’ve been a reader from the very beginning (first of all, thank you), you may recognize this look. It was in my “portfolio” for the Esquire magazine “Best Dressed Real Man in America” contest around this time two years ago (amazing how much can happen/change in 2 years).

Here is that picture, from the my personal archives:

Though the more recent photograph in the direct sun makes the silk-blend suit look slightly bronze, I assure you this is the same suit, and it is brown.

This was my first ever “slim fit” suit, purchased more than 4 years ago on eBay for about $150.

Fun Fact: My girlfriend at the time, a fellow basketball player, convinced me that the pants were too tight and needed to be let-out. I gave in. Since then, the pants have been taken-in, twice. And I’ve had several girlfriends. Hah.

Bonus Tip: Don’t let your girlfriend make your clothing decisions. Grow some b*lls and dress yourself, like a man. More often than not, gfs are not menswear experts and have bad taste in mens clothing. It makes no more sense for her to dress you than it does for you to dress her.


Oak Wool & Linen Suit

  • Grey micro-check washed cotton shirt by Steven Alan ·
  • White striped cardigan by Rag&Bone ·
  • Sneakers by Converse (Jack Purcell) ·
  • Watch by Montblanc Timewalker Automatic ·
  • Tortoise shades by Matsuda Eyewear
  • · Brown Cotton/Silk Suit

Thanks for reading.

Yours in style,

Dan Trepanier


Photography by Alex Crawford.