David Connolly
- Jun 24, 2018
- 2 min read

How to Pull off Denim-On-Denim: The 8 Dos and Don’ts

Updated: May 29, 2021

Denim on denim: It’s a tricky beast. When done correctly, it looks amazing—but one minor misstep, and you can wind up with a situation similar to the Justin Timberlake/Britney Spears debacle of 2001.

Something about the double-denim trend—often referred to as a Canadian tuxedo—feels innately wrong fashion-wise. Even when we see street style stars execute the look flawlessly, it can still be intimidating to try to pull it off ourselves.

MORE: Your Comprehensive Denim Guide for Spring 2018

With that in mind, we’ve dissected the ultimate dos and don’ts of putting together a denim-on-denim outfit.

How to Pull off Denim-On-Denim

1. DO: Play with Colors If You’re a Total Beginner

Before delving into shades of double-blue, start out by pairing different shades of denim together, like white jeans and a blue denim jacket, or black jeans and a chambray shirt. It’s almost impossible to go wrong this way.

2. DON’T: Wear Denim Accessories

Keep the jeans confined to your clothing, and just say “no” to denim shoes, a denim hat, a denim, handbag, or any other accessory.

3. DO: Use Denim Shades to Flatter or Hide Body Parts

As a general rule, lighter shades of denim draw attention to the body parts they cover, while darker washes create a slimming effect. For many women this means that dark denim jeans, and a lighter denim top or jacket is the most flattering way to go.

4. DON’T: Wear a Denim Outfit That’s All the Same Weight or Wash

You don’t want to look too matchy-matchy.

5. DO: Distress

Something about distressed denim (ripped jean shorts or jeans) just lends itself well to the denim-on-denim look—so don’t be afraid to rip away.

6. DON’T: Look to Westerns for Inspiration

Think of denim-on-denim and images of cowboys likely come to mind—and that’s not necessarily a good thing (you don’t want to end up looking like a caricature). That means staying away from accessories like cowboy boots, cowboy hats, bolo ties, and Western belts.

7. DO: Dress up Your Double Denim

Don’t be afraid to elevate your outfit with luxe-looking items, including statement heels, a tuxedo blazer, or a fabulous red lip.

8. DON’T: End up Looking like Spears and Timberlake

When in doubt, just look at the now-iconic image of Spears and Timberlake from back in the day to remind yourself just how utterly wrong denim-on-denim can go. That being said, it’ll probably be impossible for you to ever go this wrong.