100 Ways to Wear Cutoffs

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Way #1

Like this Madewell model: with more denim. It's an unexpected choice, so it's a good one.


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Way #2

With a Chanel-y chain belt, for a super-cool, stylized look we could see Kate Moss wearing while shopping in Paris.


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Way #3

Like Kate Bosworth at Coachella.


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Way #4

With front pockets, which give them a '70s babysitter kind of coolness.
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Way #5

With a skimpy bikini when you want to get up from your lounge chair and walk the beach without being too too exposed.


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Way #6

Like Lucky Community member Golden White Decor, who added just the slightest dash of leopard to dress up a denim-on-denim ensemble.


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Way #7

With high-top sneakers that'll give you some swagger.
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Way #8

Like Rachel Bilson running errands, which is always a good look.


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Way #9

With flat studded boots, so you'll look like you're dating one of the Kings of Leon.


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Way #10

Like Lucky Community member Serena Goh, who slung a jacket over her shoulders for a glamorous, fashion-y look.


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Way #11

With zippers, which make them more "edgy," whatever that means.
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Way #12

With a printed blouse, for an easy Saturday morning flea market outfit.
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Way #13

Like this street style star, who perfectly mixed faded blues with tough black accents.


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Way #14

In pink, when you want to be a little surprising.
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Way #15

With a tie-front blouse, to add a bit of retro sweetness.
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Way #16

Like Rosie Huntington-Whiteley: embellished!


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Way #17

With a tailored blazer, to mix it up a little.
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Way #18

Like Alexa Chung: with a silky blouse that's got a bit of a lingerie vibe going on.


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Way #19

With a chain strap bag, for shopping with your friends.
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Way #20

Like Lucky Community member Melissa, whose baseball cap feels so on point.


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Way #21

With turquoise jewelry that speaks to your free spirit. Or to your music festival plans.


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Way #22

With a printed sweatshirt for the ultimate cool kid uniform.


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Way #23

With espadrilles, for beach days.
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Way #24

Like Cara Delevingne: with tights when it's cold.


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Way #25

With a backpack, because backpacks are awesome.
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Way #26

Like this Alexander Wang model: with something metallic, because why not?


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Way #27

With clog-style shoes that the cool barista at your coffee shop would totally wear.
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Way #28

Like Erin Wasson: with a t-shirt that's got the same "I've had this thing for 10 years and it's cooler than most of your new stuff" appeal.


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Way #29

With friendship bracelets, just like you did at summer camp years ago.
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Way #30

Like Lucky Community member Amber Wilkerson, with a funky scarf print blazer.


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Way #31

With a printed clutch that looks like something you picked up during an exotic vacation.
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Way #32

With an eyelet top, for a friend's barbecue.


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Way #33

Like the Olsen twins. Either one, or both.


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Way #34

With a whole armful of bangles that makes fun clinky noises when you walk.
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Way #35

Like Lucky Community member Meggan Morehead, who uses cutoffs and a white top as a backdrop to let great shoes shine.


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Way #36

Studded and chained, as default concert shorts.


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Way #37

Like Alessandra Ambrosio, with a printed top that feels cheery and summery.


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Way #38

With a sheer blouse and a sporty bralette. (Rihanna would do it, no?)
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Way #39

Like DJ Harley Viera-Newton, with a sweatshirt wrapped around your waist to nail that '90s grunge vibe.


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Way #40

Dip-dyed.


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Way #41

Like Lucky Community member Ashley Torres, whose polka dot blazer makes us smile.


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Way #42

With a bright blazer and a barely-there silk camisole.
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Way #43

With a pendant necklace that'll complement a sweet floral blouse.
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Way #44

Like Alexa Chung, who looks like the perfect blend between Francophile chic and Americana classic.


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Way #45

With the prettiest of shoes and a crisp button-down.


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Way #46

Like Lucky Community member Toni Willis, who worked them into a great weekend brunch outfit.


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Way #47

With a muscle tee and a swipe of fuchsia lipstick.
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Way #48

Like Rihanna, obviously.


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Way #49

With some embroidery, because it's fun.


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Way #50

Like this Madewell model, who makes all white look super-sharp.


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Way #51

Slightly longer, so you never have to worry about your butt dimples showing. (It happens in Daisy Dukes, let's be honest.)
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Way #52

Like Revenge's Ashley Madekwe: with a tie-front blouse that shows just the smallest sliver of midriff, so it's actually wearable.


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Way #53

With a baseball tee for an easy July weekend outfit.
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Way #54

Like this Isabel Marant model: because if you're wearing printed cutoffs, you don't need to stop there. Pick a printed belt, too.


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Way #55

Like this street style star, who uses all black as a backdrop for a arty-looking jacket.


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Way #56

With cool pockets that peek out of the hems.
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Way #57

Like model Lily Donaldson: with a slouchy tank and structured blazer. So easy.


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Way #58

In shorterall form (but slightly different than Hannah on Girls.)
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Way #59

Like Erin Wasson, Alexander Wang muse and patron saint of cutoffs.


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Way #60

With a ladies-who-lunch jacket, to balance your casualness with some polish.
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Way #61

Like this DKNY look: longer, so they feel more fashion-y.


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Way #62

With an oversized button-down untucked, so you can just barely see a glimpse of shorts underneath.
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Way #63

Like Lucky Community member Noir, who's totally ready for any and all summer music festivals.


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Way #64

With glamorous, over-the-top-in-a-great-way earrings.
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Way #65

Like this street style star, who makes sneakers, shorts and a t-shirt look fashion-y.


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Way #66

In camo, to mix it up a bit.


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Way #67

Like Elizabeth Olsen, who makes us wish we wore more hats.


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Way #68

Like this Isabel Marant model: with a vest. It's very "I'm with the band."


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Way #69

With sequins, because why not?
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Way #70

Like Lucky Community member Cara McLeay, who keeps it girly up top with a pink tweed shirt.


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Way #71

With an interesting detail at the hem. (Super-easy to DIY, if you can't find a pair like these.)


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Way #72

Like Victoria's Secret Angel Candice Swanepoel, who makes a muscle tee look amazing. (That dog's a pretty great accessory, too.)


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Way #73

In a fun print that's not too loud.


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Way #74

Like Maria Menounos: as a cover-up for your bottom half only.


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Way #75

With patchwork denim, for a fresh spin on the denim tuxedo.


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Way #76

Like this Twenty8Twelve model: with a wrap-front blouse for an airy outfit ideal for way-too-hot summer days.


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Way #77

With floral embroidery that you'll want to get up close to to check out.


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Way #78

Like Lucky Community member Chezka, who mixes a sporty bomber jacket with girly pink shorts.


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Way #79

With something, anything leopard.
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Way #80

Like this Diesel Black Gold model, who let her button-down peek out from underneath her shorts. It's a super-fashiony look, but a cool one if you're going for unexpected layers.


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Way #81

With opaque black tights, when it's too cold to go bare-legged.
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Way #82

Like this model, who has the best slouchy-cool proportions going on.


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Way #83

With a floppy hat, for a picnic in the sun.


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Way #84

Like this Erin Wasson x RVCA model: with garters. (Or maybe just fishnet tights, which is a little easier to pull off if you keep it conservative up top.)


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Way #85

In a punchy pattern, like these preppy windowpane checks.
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Way #86

Like Lucky Community member Nik G., who's got a good mix of girliness on top and swagger on bottom.


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Way #87

With a striped shirt Taylor Swift would love.


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Way #88

Like Erin Wasson, in her white-on-white-on-white fierceness.


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Way #89

As a bermuda short, which can actually be really flattering.


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Way #90

Like Lucky Community member Brittany Olson, who keeps it classic with her black and white palette.


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Way #91

Like this DSquared2 model, except maybe a little more toned-down.


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Way #92

With a chunky sweater, to keep you warm during a nighttime beach party.
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Way #93

Like this street style star. We can't tell if she's wearing shorts or pants or what to call them, but the hybrid cutoff style is super-cool.


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Way #94

With aviators, of course.
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Way #95

Like this Balmain model: with intentionally-ripped fishnets. (Just keep the rest of the look covered up so it's not too scandalous.)


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Way #96

In an unexpected color, like pale brown.
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Way #97

With a pajama top, for a eclectic, nonchalant weekend look.


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Way #98

Like Camilla Belle, with an eyelet top and sleek high ponytail for a look that's more on the polished side.


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Way #99

Black and floral, so they're a little tough but also feminine.
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Way #100

Like Lucky Community member Bindi Singh, whose dip-dyed ones are a notch more interesting than basic blues.


Digital Fashion Writer

If we were playing a word association game and you said "cutoffs," I'd have a zillion things to blurt out: triangle bikini tops, beach towels, Dazed and Confused, summer concerts, white tank tops, Britney Spears in the early '00s. But if we were playing "Let's Get Dressed for Weekend Errands/Concerts/Brunches" and you reached for cutoffs first, I wouldn't have nearly as many things to fire back. But now, all that's changing.

Sure, I've got all the familiar templates stamped into my mind: cutoffs + a printed chiffon-y blouse and sandals; cutoffs + a slouchy t-shirt and sneakers. You know. But there are tons of other ways to wear them beyond those defaults, as you'll learn below. With 100 (yes, one hundred) unexpected ways to wear them—about the same number of days as there between now and Labor Day—there's really no excuse not to try a cutoffs outfit at least once this summer. Or, say, 90 times.

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