The High/Low: Tailored Jackets & Hoodies

February 5th, 2012

As I’ve written many times (since 2009), my favorite way to dress is what I sometimes call High/Low. A classic silhouette with a combination of dressy/casual and luxury/affordable. It’s an easy formula for an outfit that is stylish but not “too much” in any direction.

An example of High/Low is a simple hoody (preferably neutral and solid) combined with a tailored jacket (suit or blazer).

I am partial to this particular combination because it is very me and represents my style influences – mixing athletic elements as a former basketball player and tailored elements as a current menswear designer/ “tailor’s apprentice”.

Here’s a couple examples I wore last week.

1. Grey on Grey

I hear it from guys all the time: “I want to wear suits and tailored pieces more often, but I never have occasions to wear them.” Here’s an easy solution: you don’t need an “occasion”,  just wear your suit. Men look good in suits. Girls like it. Your parents like it. And most importantly, YOU like it.

The best part is, it’s easy. The jacket matches the pants…75% of your outfit is already put together.

There are plenty of “laidback” suits on the market now – from Uniqlo to Michael Bastian. Soft shoulders, partial lining, textured fabric, slim leg, etc. These are the easiest to wear casually – with sneakers, for example.

However, that doesn’t mean you can’t dress-down a sharp suit. This charcoal grey peak lapel number sometimes serves as my “semi formal” suit.

As always, fit is critical.


Charcoal Essential Suit

  • Grey hoody by Theory ·
  • Tortoise shell prescription glasses (w/ clip on shades) by Garrett Leight ·
  • Oxblood loafers by Scarpe di Bianco ·
  • White sneakers by Nike ·
  • White t-shirt by Alexander Wang
  • · Grey wool suit

2. Navy on Navy

The right blazer can sharpen a very casual look and take it up a level. This is just a simple casual look – hoody, jeans, boots – with the “perfect blue blazer” from my collection over it.

Sometimes going without a pocket square is more natural. When it’s a really laid back look, you don’t need to add a fussy accessory like a pocket square.

  • Navy pullover hoody by Club Monaco ·
  • Light grey wash jeans by Ralph Lauren Polo ·
  • Black leather wingtip boots by Paul Smith ·
  • Black aviator shades by Persol

3. Suit & Sneakers


Like I said, easiest done with a more casual suit, like an olive green cotton.


Thanks for reading.

Yours in style,

Dan Trepanier


Photography by Alex Crawford.