How to Wear Boyfriend Jeans (4 Dos and 3 Don’ts)

Boyfriend jeans are a favorite pick for off-duty models and celebrities. Get the look right and you have an ensemble that’s carefree, casual and chic all rolled into one. Get it wrong and — well, it’s not the end of the world to have a bad outfit day, but we’re just not gonna let that happen. Read on for our dos and don’ts on how to wear boyfriend jeans.

And at the end, we have five boyfriend jean outfit formulas for you to copy!

Dos and Don’ts of Wearing Boyfriend Jeans

Do roll them up.

Boyfriend jeans have a loose fit, which can easily morph into sloppy. Keep the look tidy by rolling them up loosely to a crop length. They should sit a few inches above your ankle, but this isn’t a hard-and-fast rule. Go with the length that feels right, based on your height and the choice of shoes. Better yet, ask a friend for a second opinion.

Do demand a tapered leg.

Pay attention to how the entire jean hangs on your leg after you roll them. You should see an even taper with a slightly tighter ankle. If the jeans hang straight down or even get wider towards the ankle, that’s generally going to create an unflattering, blocky look. Blame this on the jeans and try a different pair.

how to wear boyfriend jeans

Do experiment with washes.

Models and celebrities favor the ultra light wash boyfriend jeans that have some level of distress to them. In your own wardrobe, mix it up with dark- or medium-wash jeans. Even a colored or white jean (yes, even in winter!) could work well. As for the rips and tears that celebs seem to love so much, go easy on them. Excessively torn-up jeans aren’t practical and they rarely look great on anyone.

how to wear boyfriend jeans

Hatty High Waisted Black Boyfriend Jeans, $31, Boohoo

Do wear a belt and tuck in your top.

Boyfriend jeans fit loose and straight, like joggers. A belt and tucked-in top ensures you have a waist, and also gives your outfit an intentional quality. Let the world know you put this outfit together (and you did not just grab stuff from the closet in the dark).

Do have fun with your choice of shoes.

how to wear boyfriend jeans

From left to right: (1) Catherine Slim Boyfriend Jeans, $53.70, Nordstrom (2) Boyfriend Mid-Rise Skinny Ankle Jeans, $28, OldNavy (3) ASOS KIMMI Shrunken Boyfriend Jeans In Clover Mid Stonewash with Raw Hem Turn-up, $49, ASOS

It’s hard to pick the wrong shoe for the boyfriend jean. UGGs and tall boots wouldn’t work so well, but pumps, sandals, ankle boots, flats and sneakers are all good choices. You could even pair ankle socks with heels for a cute retro look. Have fun with it!

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Catherine Brock

Catherine Brock is a writer, editor and marketer who's been sharing wisdom online since 2002. She's been featured on, and ABC7 Chicago, FOX2News St. Louis and KCAL9 Los Angeles. Connect with Catherine on LinkedIn, Instagram, or Twitter. Learn more about Catherine.
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