How to Wear Jeans to the Office

July 19th, 2011

If you’re denim has the right cut – think slim and straight – there is no reason you can’t dress it up.

Depending on your office of course, these looks may give you ideas for good Casual Friday looks that can transfer directly to a “fancy” weekend night out.

As a matter of fact, in a lot of professions you may not need to wait until Friday. If you can make your denim look sharp and presentable nobody will call you out on looking “not appropriate”.

Here’s three different pairs of jeans dress-up, to get you thinking.

The Easy Way


If you’re unsure about dressing-up jeans, take the easy way out. Dark, slim, straight, hardly any contrast stitching, and hemmed to the top of the back of the shoe. Can’t really go wrong here.

Tip: You may have noticed in the close-up shots that every jacket in this post has some texture to it. The more “rugged” the fabric, the easier it is to pair with denim.

Tip II: A soft shoulder can help give a slighty more relaxed, denim-friendly feel as well.

Tip III: The tie in this look (and look 1) is cut from the same cloth (literally) as the DB jacket in look 2. Worn together they ad an element of simplicity that is new and fresh.  Wool ties aren’t just for the winter, keep in mind there are awesome lightweight textured wools too.

Olive Worsted Suit

Brown Gingham Shirt

Modern DB/Vintage Denim


Looking for a new pair of jeans? Get a pair of old jeans instead. As we all know, denim gets better with age. So why pay $300 for a pair of fake-washed jeans, when you can get an authentically broken-in pair of American classics for $20?

Tip: Yes, even your favorite beat-up jeans can be dressed up, as long as they still fit properly. If they’ve stretched over time, you may need to have them altered a little to coincide with the silhouette of your slim jackets.

Tip II: Slippers are a great style-forward city man’s alternative to boat shoes. I find it a bit strange how many people are wearing boat shoes now, especially in the concrete jungle.

Tip III: Again, if you’re going to roll your jeans with a “dressed-up” look, make it clean and crisp.

Tip IV: Brown + Blue. Get with it.

  • Forest green velvet slippers by Del Toro ·
  • Distressed jeans by Levis Vintage ·
  • Madras pocket square by Fine and Dandy Shop ·
  • Tortoise aviator shades by Ralph Lauren Purple Label ·
  • White poplin shirt ·
  • Watch by Montblanc Timewalker Automatic
  • · Brown hopsack double breasted suit jacket

Worsted Wool Suit in Coffee

White Works Too

I know, I’ve been wearing these white jeans a lot lately – but they work with everything. I once wore them for three days straight, with three completely different looks (even slept in them one drunken night…yes, they were quite dirty afterwords).

Tip: Everything in this look can be considered a (take on) menswear classics. Blue blazer, pink shirt, simple stripe rep tie, straight denim, monkstrap shoes, aviator shades. Classic items are very easy to pair together, making it hard to go wrong.

Tip II: If you’re as big of a white denim fan as I am, get to know your bleach bottle, or your dry cleaner.

  • Pink cotton shirt ·
  • Tortoise aviator shades by Ralph Lauren Purple Label ·
  • Brown alligator belt by Ralph Lauren Purple Label ·
  • White denim jeans by Helmut Lang ·
  • Watch by Montblanc Timewalker Automatic ·
  • Leather/suede double monkstrap shoes by Scarpe di Bianco ·
  • Brown striped tie by Ralph Lauren Black Label

Thanks for reading.

Yours in style,

Dan Trepanier

Photography by Clark Shaw. 

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