How to Wear Boyfriend Jeans for Any Occasion

The popular silhouette is more versatile than you think.

How to Wear Boyfriend Jeans Ashley Graham

@ashleygraham/Design by Cristina Cianci

Beating skinny jeans as the preferred silhouette, boyfriend jeans have become a fan-favorite staple among Gen-Z and millennials alike. The slightly tailored cut is revered for its distinct high waist and comes in a range of washes. But it’s the versatility of the style—its ability to go with, basically, anything—that’s really cemented its spot as a true wardrobe icon. 

Whether you have plans to dress your pair up with heels or prefer to keep your denim casual, you have options when it comes to boyfriend jeans. This relaxed fit is especially great for desk-to-drink situations that call for quick outfit changes at a moment’s notice. This means they can just as easily create a smart ensemble when paired with an oversized blazer and loafers, as they can hit the town by simply swapping out the brogues for a pair of mules or pumps. 

For those who still aren't quite sure how to wear boyfriend jeans, just ahead are 11 outfit ideas suited to fit an array of lifestyles, personal aesthetics, and occasions, too.

01 of 11

The Everyday Outfit

Design by Tiana Crispino

Design by Tiana Crispino

Give your boyfriend jeans a casual yet elevated feel with a collared bodysuit and platform sandals. Add luxe accessories, like a pair of trend-forward sunglasses or a statement bag to complete the look.

BDG Premium High-Waisted Retro Boy Jeans
BDG Premium High-Waisted Retro Boy Jeans $99
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Jacquemus Yauco Buttoned Rib-Knitted Bodysuit
Jacquemus Yauco Buttoned Rib-Knitted Bodysuit $350
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Vagabond Courtney Sandals
Vagabond Courtney Sandals $120
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Bottega Veneta Eyewear Rectangle Sunglasses
Bottega Veneta Eyewear Rectangle Sunglasses $350
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02 of 11

The Sneaker Outfit

Design by Tiana Crispino

Design by Tiana Crispino

When wearing sneakers with your boyfriend jeans, balance the super-relaxed feel with minimally chic pairings so that the outfit doesn’t feel too informal.

Levi's 501 Original Fit Jeans
Levi's 501 Original Fit Jeans $98
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K.ngsley Dark Olive "Fist" Ribbed Tank
K.ngsley Dark Olive "Fist" Ribbed Tank $180
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Saucony Jazz Court
Saucony Jazz Court $90
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Elisa Johnson Jane Sunglasses
Elisa Johnson Jane Sunglasses $140
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03 of 11

The Beach-to-Street Outfit

Design by Tiana Crispino

Design by Tiana Crispino

Next time you’re on vacation, slip a pair of distressed boyfriend jeans over your bikini to wear the look both poolside and to dinner right after.

Ksubi Playback Distressed Straight-Leg Jeans
Ksubi Playback Distressed Straight-Leg Jeans $240
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Riot Swim Wave Top
Riot Swim Wave Top $79
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Local European Nuria Oversized Blouse
Local European Nuria Oversized Blouse $93
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Tkees Riley Vegan Sandals
Tkees Riley Vegan Sandals $50
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04 of 11

The Desk-to-Drinks Outfit

Design by Tiana Crispino

Design by Tiana Crispino

Similarly, wearing boyfriend jeans also works well when transitioning between night and day. All you need are a few quick accessory changes to alter the overall feel of the ensemble.

Agolde Grey '90s Mid-Rise Loose Fit Jeans
Agolde Grey '90s Mid-Rise Loose Fit Jeans $190
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Drae Black Square-Neck Top
Drae Black Square-Neck Top $81
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Rejina Pyo Allie Mules
Rejina Pyo Allie Mules $329
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Edas Maria Bag
Edas Maria Bag $395
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05 of 11

The Off-Duty Model Outfit

Design by Tiana Crispino

Design by Tiana Crispino

Embody your favorite supermodel on their day off by pairing a second-skin tee with boyfriend jeans, hoops, and a logo-emblazoned baseball cap.

Skims Stretch Cotton Tee
Skims Stretch Cotton Tee $48
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R13 Baseball Cap
R13 Baseball Cap $65
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Lili Claspe Dani Hoops
Lili Claspe Dani Hoops $90
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Gucci Distressed Organic Boyfriend Jeans
Gucci Distressed Organic Boyfriend Jeans $890
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06 of 11

The Smart Blazer Outfit

Design by Tiana Crispino

Design by Tiana Crispino

A key tip in wearing boyfriend jeans to the office is adding smart pairings into the mix. Give the look a little extra lift with strappy mules.

Reformation Cynthia High Rise Straight Long Jeans
Reformation Cynthia High Rise Straight Long Jeans $138
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Frankie Shop Hourglass Cotton Blazer
Frankie Shop Hourglass Cotton Blazer $210
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Gia Couture x Pernille Teisbaek Puffer Slide Sandals
Gia Couture x Pernille Teisbaek Puffer Slide Sandals $425
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Mansur Gavriel Pencil Bag
Mansur Gavriel Pencil Bag $495
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07 of 11

The Trend-Driven Oufit

Design by Tiana Crispino

Design by Tiana Crispino

Looking to make a statement? Try slipping a long tunic or dress over your jeans for a cool, layered look. Also, don’t be afraid to play with color—add complementary accessories but don't necessarily match conventionally.

Paloma Wool No. 758 Jenny Dress
Paloma Wool No. 758/Jenny Dress $182
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The Attico High-Rise Straight-Leg Jeans
The Attico High-Rise Straight-Leg Jeans $303
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Amina Muaddi Gilda Embellished Satin Mules
Amina Muaddi Gilda Embellished Satin Mules $929
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Byfar Baby Amber Moc-Croc Shoulder Bag
Byfar Baby Amber Moc-Croc Shoulder Bag $364
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08 of 11

The Effortlessly Cool Outfit

Design by Tiana Crispino

Design by Tiana Crispino

On days that may call for a little less effort, all you need is a graphic bowler-style shirt and sporty sandals of the variety we've seen all over Instagram.

& Other Stories Keeper Cut Jeans
& Other Stories Keeper Cut Jeans $89
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Frankie's Bikinis Fifi Button Up Shirt
Frankie's Bikinis Fifi Button Up Shirt $185
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Jil Sander Off-White Leather Chunky Sandals
Jil Sander Off-White Leather Chunky Sandals $940
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Cult Gaia Katka Sunglasses
Cult Gaia Katka Sunglasses $228
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09 of 11

The Transitional Outfit

Design by Tiana Crispino

Design by Tiana Crispino

When the weather is a bit unpredictable, opt for convertible layers and slip-on footwear that you can wear with or without socks, should conditions change dramatically.

Good American Mom Jeans
Good American Mom Jeans $149
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Source Unknown Detachable Sleeve Linen Knit
Source Unknown Detachable Sleeve Linen Knit $136
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Hyusto Quincy Slippers
Hyusto Quincy Slippers $323
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Advene The Age Bag
Advene The Age Bag $495
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10 of 11

The Early 2000s Outfit

Design by Tiana Crispino

Design by Tiana Crispino

The early aughts are back, and all you need to recreate a Y2K look for 2021 is a fitted, cropped T-shirt and a vintage bag.

Heaven by Marc Jacobs Crochet Teddy Baby Tee
Heaven by Marc Jacobs Crochet Teddy Baby Tee $75
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Denimist Distressed Boyfriend Jeans
Denimist Distressed Boyfriend Jeans $158
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Pêche Layla Sandals
Pêche Layla Sandals $86
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Louis Vuitton Monogram Multicolor Pochette
Louis Vuitton Monogram Multicolor Pochette $1015
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11 of 11

The Plain White T-Shirt Outfit

Design by Tiana Crispino

Design by Tiana Crispino

Sometimes you want to wear boyfriend jeans and a plain white tee. In that case, add tall leather boots and a trucker jacket to round out the look.

Eloquii Classic Fit Distressed Boyfriend Jeans
Eloquii Classic Fit Distressed Boyfriend Jeans $100
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Universal Standard Foundation Short Sleeve Crew Neck Tee
Universal Standard Foundation Short Sleeve Crew Neck Tee $48
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Frye Campus 14L Boots
Frye Campus 14L Boots $398
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Brixton Women's Utopia Corduroy Jacket
Brixton Utopia Corduroy Jacket $109
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