The 8 Dos and Don’ts of Wearing Denim on Denim

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: How to Wear a Denim Shirt in 25 Different Ways

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

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.

Photo: Imaxtree

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.

Photo: Song of Style

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.

MORE: Behold: A Complete Guide to Wearing High-Waisted Jeans

8. DON’T: Ever end up looking like Spears and Timberlake, for the love of all things holy

When in doubt, just look at this 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 #neverforget.

Photo: Getty Images

 Originally published August 2014. Updated May 2017.