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.
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.
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.
A version of this article was originally published in August 2014.