5 Jeans: The Perfect Denim Wardrobe

April 6th, 2016

I’m typically more of a trousers guy myself, but that doesn’t mean you won’t catch me in a pair of jeans from time to time.

The right denim fits most of my criteria for a good wardrobe investment: a durable fabric that builds character over time, a timeless design that can be worn for years and years, and a versatile garment that can be worn with everything from a t-shirt to a bespoke jacket.

In my opinion the perfect denim wardrobe consists of only five pairs of jeans:

Tailored Indigo


For your raw indigo pair, have them tailored to fit like your trousers, because you’re most likely to wear these with tailored jackets. These APC jeans, for example, have been hemmed with no-break making them ideal for loafers and sharp dress boots.

Cropped White


If you haven’t scooped a pair of white jeans, tis the season. You will be surprised at how much these amp up your Spring/Summer wardrobe. I like mine cropped for the warmer weather, although hem break is largely a personal preference.

Slim Black


For your black pair, make them a little skinnier and a little longer – don’t be afraid of a little pooling at the ankle. The distressing around the knees is very current and on-trend, but can be tasteful if done subtly.

Vintage Wash


A good light wash pair can be hard to find, since so many of them look weirdly and fakely distressed. I picked up these vintage Levi’s 501s from a vintage shop and have been wearing them with everything – yes, including a cream DB linen jacket. 1970’s inspired.

Cool Grey


Medium grey in a cool hue – arguably as versatile as the dark indigo, but much more rare and underrated.

Things to avoid when buying jeans:

  1. Back pocket “designs”
  2. Embellishments of any kind (rivets, heavy stitching, paint splatter, etc)
  3. A low rise jeans that doesn’t fit your natural waist

Things to know when buying jeans:

  1. They will stretch out, a lot. When you first buy them they should be very snug in the waist, seat and thigh.
  2. Wear them several times before you have them tailored, you want to make sure they are fully broken-in out before altering the fit.
  3. Some people have crazy rituals with washing their jeans…you’ll have to find what works for you.


Thanks, as always, for reading.

Yours in style,

Dan Trepanier

Photography by Alex Crawford.

  • Philipp

    The Slim Black are pure gold! Thanks man!


  • TheWolvesden

    Grey jeans are deeply underrated. Rocking a pair for this conference I am going to this weekend.

  • Miguel

    Excellent post.

  • Kyle Leon Norville

    Ironically enough I have been trying to figure out which denim to get. I have horrible history with denim at this point ( specifically with the crotch ripping on me). Trying to invest in a pair of black and vintage washed denim. Any suggestions for brands? ( tried Gap, Levi’s, and J Crew and no luck)

    • Reuben

      I just bought a pair from Nordstrom (Joe’s) give them a Try, I love them.
      Thanks, Joe’s ‘Classic – Spotless’ Straight Leg Jeans (Warbucks).

  • Dirk Gently

    Love this article! As a frequent complainer here in the comments, I appreciate this “TSBMen-esque” post very much. Thanks for listening, Dan, and trying to accommodate us all.

    (BTW, I appreciate the need to monetize the blog and make a living and I don’t begrudge you that. There are just not a lot of sources out there for great content like this post, and your editorial voice is very strong, so these articles have been missed!)

  • LarsBrown.

    My jean game has been a little off recently – I haven’t been giving it the attention required – so this is good inspiration to freshen it up.

    Dan (and anyone else who appreciates a raw denim), I’d implore you to check out Huit Denim. They’re a small factory in Wales who produce some awsome jeans. Big believers in the ‘slow fashion’ philosophy. International shipping and all that fun stuff…

  • NickH

    Jeans, no thanks.

    • http://www.TSBmen.com/ Dan Trepanier

      Not the same class as tweed trousers. Cheers NH :)

      • NickH

        Three years ago I threw every pair I owned away and it was the best decision ever. I was never able to find a pair that fit like a good pair of chinos. Girlfriend hates it because I’m always “overdressed” but I call it liberation.

  • rhone04

    great article, Dan!

    • http://www.TSBmen.com/ Dan Trepanier

      Appreciate you.

  • Terrified T

    Where are the mid grey jeans from? Those are clean…

  • Alex G

    Been waiting on a post like this! Are any of the tailored pieced from the AoS collection?

    • http://www.TSBmen.com/ Dan Trepanier

      Hey Alex. These are all older pieces, from before the collection. We have access to some very similar fabrics, however. If there’s something you like, just shoot me an email and we can show you some swatches and get started with your fittings :) Cheers brother

  • tommyjohn_45

    Good post! Would love to know more about proper fit. I always struggle to find the right jean. Definitely need to give black and grey a try, but not quite ready to pull of the white ;)…

    • AdamE

      Proper fit for jeans is a bit like the boxers vs. briefs debate… That said, I’m a big fan of the slim not skinny mantra, much the same as I am with trousers, chinos, shorts, and just about anything I wear on my lower body over the aforementioned undergarments (boxer briefs BTW, best of both worlds…)…
      Right now I stick to raw indigo, in various stages of break in (I recently retired my favorite pair, because of blow-outs in the crotch/seat area beyond patching (I had patched them many times, but it was becoming too obvious))… The grey ones look awesome… Black give me flashbacks to middle school, and the light washes give me mild PTSD to the late 80s early 90s acid wash… and Obama’s dad jeans… White is a great look, but the lids at most of our local coffee shops are too dicey for me to make the leap, the odds of them staying white beyond a couple of wears are exponentially low, and nobody wants to explain random brown stains on white pants…

    • TO

      To me, the best fitting pair in this article is “vintage wash”. Can’t go wrong if that’s how your jeans fit!