This Is How to Pull Off Double Denim Like a Street Style Pro

What is it about denim on denim that feels so quintessentially cool? It’s a low-effort, high-yield layering trick that’s remarkably easy to pull off, no matter the wash. For 2025, mixing and matching your assortment of denim separates is all about keeping an open mind. While a classic jacket and jean combination always does the trick, timely silhouettes—such as nipped-in waistcoats worn with bootcut jeans—are shifting into focus now that the weather is warming up.

For those well-versed in the versatile joys of the Canadian tuxedo, this shopping guide will help flesh out any lingering gaps in your wardrobe. (Don’t sleep on belted jean jackets!) That said, if your approach to denim tends to err on the side of restraint, rest assured these pairing ideas won’t feel over the top. We looked to street style for inspiration and found six ways to wear denim on denim this year, leaning on blue jean mainstays from the likes of Levi’s, Madewell, and Favorite Daughter.

A pair of jeans that fits like a glove is no doubt a holy grail find in the denim world, but its unsung cousin? The boldly baggy silhouette. Not only is a relaxed fit inherently more comfortable to wear, but it also oozes a sort of insouciance that skinnies simply cannot pull off. For crisper temperatures, style a loose jacket with your go-to roomy jeans. Once it’s warm out, switch to a baggy button-down and wear with your staple jeans or a pair of oversized shorts.

For all of its good qualities, we’ll concede that denim can feel a bit too casual for certain occasions. The exception? Denim crafted in smooth, clean lines. Rather than reaching for the usual suspects, like a cropped buttoned jacket, slip into streamlined silhouettes like tunics and popover tops to help add polish to any layered look. Minimal, sculptural jewelry is a good finishing touch.

You may already have an affinity for vests, the elegant alternative to the tank top. And though waistcoats and cutaway vests are often crafted in tailoring materials like crêpe fabrics, there’s something about a denim iteration that feels stylishly rebellious. Wear yours with jeans that offer a roomier silhouette—bootcut, baggy, or wide legs are all great options. Or, a longline denim skirt also makes a stylish pairing (extra points if it’s in the same wash for a monochromatic effect).

Nothing can replace our jean jackets (nothing!), but sometimes an outfit calls for a silhouette that’s slightly more refined. Enter: the tie-waist belt. Denim jackets with this extra accessory feel a little bit ’70s and a whole lot chic. Styling is fairly painless: Wear with jeans (we love the bootcut with this) or try layering it with a matching skirt for a fresh spin on the skirt suit.

The denim skirt renaissance lives on. Whether you’re more of an A-line midi type or prefer maxi-length hems, this piece can pair well with a variety of denim toppers. For example, tuck a jean shirt into your skirt and accessorize with simple flat sandals for a mid-week coffee date. Easy. Or if you’ve got a cropped denim shell in your closet, team it with a mid- or low-rise skirt to allow for a slight peek of skin at the waistline. One thing to keep in mind: The longer the skirt, the lighter you should go on the denim up top to avoid an overwhelming pairing.

Make your khaki trench coat jealous with a denim iteration that you can mix and match with all of your favorite jeans. With its lighter material, it’s the perfect piece to transition between seasons—and it’s eye-catching no matter how you style it. Right now, we’re loving a ’90s-meets-early-aughts interpretation, featuring a denim trench with baggy jeans, a shrunken tee, and finished off with a cord necklace and ballet flats.

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