#44: How to wear a Canadian Tuxedo without looking like Britney and Justin

Double the pleasure, double the fun. Double the denim!

Lindsay Sword

Today’s topic is a fun one. We’re doubling down on double denim aka the Canadian Tuxedo (more on that below) aka denim-on-denim (what we call it in the biz).

Full credit goes to my work wife and long-time friend, who suggested this idea after Kendrick Lamar and I both rocked double denim this week. (His look looked especially good with multiple Grammy awards!)

I fell asleep and missed the Grammys, so this was an unintentional twinning! (Kenrick by Kevin Winter//Getty Images; Me by Me//My iPhone)

It’s no secret that I am a huge fan of denim. I’ve written about it here and here and here (it could easily be the workhorse of my wardrobe).

But as an elder millennial who brain was burned by this image…

Britney and Justin at the 2001 VMAs (P.S. We’re obviously Team Britney here.)

It’s taken me a little while to figure out how to wear denim with denim that doesn’t get me in double trouble.

(Which, ironically, was why the Canadian Tuxedo was invented in the first place. Because Bing Crosby got in dress code trouble for wearing Levi’s jeans at a fancy Vancouver hotel. When Levi’s heard about this, they created a formal tuxedo jacket made from their denim just for him.1)

Bing Crosby in his natural element & rocking his denim tuxedo c/o Levi’s

But thanks to some excellent inspiration that I’ve gathered and studied over the years, I think I’ve cracked the code on how to wear it.

My Do’s and Don’ts for Denim-on-Denim:

DO wear similar shades (washes) on top and bottom
DON’T lean too hard into the Western vibes
DO layer, t-shirts under, blazers over, etc.
DON’T wear a cowboy hat 😉
DO accent with rich reds, burgundys and neutrals like camel, tobacco, and chocolate browns
DON’T mix with brights or neons (right now at least, too Jenna Lyons J.Crew for the moment, but I could see it coming back and I’d be first in line!)
DO pair with prints, like cheetah, zebra, even snakeskin in small doses (like my boots above)
DON’T pair with polka dots, or other overly bold, graphic prints. Small scale is better.
DO accessorize with polished jewelry, pointy-toed shoes, and preppy elements like loafers
DON’T go overly dressy, avoid stilettos and Britney-style Swarovski!!

The beauty of double denim is how it casually makes a statement. It’s classic Americana without feeling classic. Cowboy swagger without having to learn how to ride a horse. Laid-back but a step ahead of jeans and a tee shirt. Minimal with a maximalist impact. Midimalist, if you will.