The 6 Rules of Wearing a Jean Jacket in 2021

We love the ease of a loose-fitting denim jacket, but sleeves that go way past your wrists (or even past your finger tips) can leave you looking like a kid playing dress up, especially if you’re petite. The solution is simple—just roll the cuffs up so the end of the sleeves hit somewhere between your wrist and three inches above your hands. This shows just enough skin to avoid you being swallowed up by your outerwear, without exposing you to too much crisp fall air.

Shop similar styles: Urban Renewal jacket ($69); Club Monaco sweater ($170); Wit & Wisdom jeans ($78); Converse sneakers ($60)

This doesn’t necessarily have to mean skinny jeans or leggings, but whatever pants you choose, they should fit fairly close to the leg to help you maintain some shape and avoid turning into a denim blob. Skinny jeans, straight-leg and other slim-fit cuts are ideal while Boyfriend jeans, flares and ‘90s skater styles are better paired with a cropped jacket. P.S. Adding a heeled bootie can also help elongate your stems and balance an oversize jacket up top.)

Shop similar styles: Outland Denim jacket ($265); BP turtleneck ($19); Frame jeans ($228); Frye boots ($398; $239)

Wearing a longer, looser jacket over a minidress or shorts might leave you looking like an apple propped up on two popsicle sticks. A jacket that hits right at your hips, or even higher at your natural waist, helps maintain your proportions in a more flattering way.

Shop similar styles: Roxy jacket ($80); Goodlife T-shirt ($60); Lee shorts ($68); UO shoes ($59)

If you’re going to rock head-to-toe denim, we recommend choosing a variety of washes rather than trying to match pieces together. Pale chambray shirts, deep blue jeans, distressed jackets, acid washes—feel free to mix things up with wild abandon. You could even add in some black, gray or white wash denim if you wanted, but save the patterned or colorful options for a different ensemble.

Shop similar styles: Reformation jacket ($112); Rails shirt ($158); Noend jeans ($158); Børn boots ($165; $115)

On the other hand, if you prefer a totally monochrome look, opt for pieces from the same brand in the exact same color or wash. We prefer bright hues, patterned options or neat black or white washes over any classic blue jeans. They feel much more modern and fresh, and don’t run any risk of making you look like a rancher lost in the big city.

Shop similar styles: Hidden Jeans jacket ($98) and jeans ($80); Reformation jacket ($148) and jeans ($178); Outdoor Voices T-shirt ($38); Cole Haan loafers ($160; $96)

Layering your outerwear is a fun way to get more use out of lighter jackets while adding depth to your ensemble. And while we love our classic denim styles, they aren’t the most exciting to look at. This is why we suggest layering them under your plaid blazer or floral trench coat, rather than on top. You’ll still get that bonus warmth and a fun pop of blue, but it looks much more fashion forward than having a plain denim jacket front and center.

Shop similar styles: Reformation blazer ($174); Wash Lab jacket ($138; $83); AG turtleneck ($138); PTCL jeans ($45); Marc Fisher Ltd boots ($179)