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Way #1
Like this Madewell model: with more denim. It's an unexpected choice, so it's a good one.
Way #2
With a Chanel-y chain belt, for a super-cool, stylized look we could see Kate Moss wearing while shopping in Paris.
Way #3
Like Kate Bosworth at Coachella.
Way #4
With front pockets, which give them a '70s babysitter kind of coolness.
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.
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.
Way #7
With high-top sneakers that'll give you some swagger.
Way #8
Like Rachel Bilson running errands, which is always a good look.
Way #9
With flat studded boots, so you'll look like you're dating one of the Kings of Leon.
Way #10
Like Lucky Community member Serena Goh, who slung a jacket over her shoulders for a glamorous, fashion-y look.
Way #11
With zippers, which make them more "edgy," whatever that means.
Way #12
With a printed blouse, for an easy Saturday morning flea market outfit.
Way #13
Like this street style star, who perfectly mixed faded blues with tough black accents.
Way #14
In pink, when you want to be a little surprising.
Way #15
With a tie-front blouse, to add a bit of retro sweetness.
Way #16
Like Rosie Huntington-Whiteley: embellished!
Way #17
With a tailored blazer, to mix it up a little.
Way #18
Like Alexa Chung: with a silky blouse that's got a bit of a lingerie vibe going on.
Way #19
With a chain strap bag, for shopping with your friends.
Way #20
Like Lucky Community member Melissa, whose baseball cap feels so on point.
Way #21
With turquoise jewelry that speaks to your free spirit. Or to your music festival plans.
Way #22
With a printed sweatshirt for the ultimate cool kid uniform.
Way #23
With espadrilles, for beach days.
Way #24
Like Cara Delevingne: with tights when it's cold.
Way #25
With a backpack, because backpacks are awesome.
Way #26
Like this Alexander Wang model: with something metallic, because why not?
Way #27
With clog-style shoes that the cool barista at your coffee shop would totally wear.
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.
Way #29
With friendship bracelets, just like you did at summer camp years ago.
Way #30
Like Lucky Community member Amber Wilkerson, with a funky scarf print blazer.
Way #31
With a printed clutch that looks like something you picked up during an exotic vacation.
Way #32
With an eyelet top, for a friend's barbecue.
Way #33
Like the Olsen twins. Either one, or both.
Way #34
With a whole armful of bangles that makes fun clinky noises when you walk.
Way #35
Like Lucky Community member Meggan Morehead, who uses cutoffs and a white top as a backdrop to let great shoes shine.
Way #36
Studded and chained, as default concert shorts.
Way #37
Like Alessandra Ambrosio, with a printed top that feels cheery and summery.
Way #38
With a sheer blouse and a sporty bralette. (Rihanna would do it, no?)
Way #39
Like DJ Harley Viera-Newton, with a sweatshirt wrapped around your waist to nail that '90s grunge vibe.
Way #40
Dip-dyed.
Way #41
Like Lucky Community member Ashley Torres, whose polka dot blazer makes us smile.
Way #42
With a bright blazer and a barely-there silk camisole.
Way #43
With a pendant necklace that'll complement a sweet floral blouse.
Way #44
Like Alexa Chung, who looks like the perfect blend between Francophile chic and Americana classic.
Way #45
With the prettiest of shoes and a crisp button-down.
Way #46
Like Lucky Community member Toni Willis, who worked them into a great weekend brunch outfit.
Way #47
With a muscle tee and a swipe of fuchsia lipstick.
Way #48
Like Rihanna, obviously.
Way #49
With some embroidery, because it's fun.
Way #50
Like this Madewell model, who makes all white look super-sharp.
Way #51
Slightly longer, so you never have to worry about your butt dimples showing. (It happens in Daisy Dukes, let's be honest.)
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.
Way #53
With a baseball tee for an easy July weekend outfit.
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.
Way #55
Like this street style star, who uses all black as a backdrop for a arty-looking jacket.
Way #56
With cool pockets that peek out of the hems.
Way #57
Like model Lily Donaldson: with a slouchy tank and structured blazer. So easy.
Way #58
In shorterall form (but slightly different than Hannah on Girls.)
Way #59
Like Erin Wasson, Alexander Wang muse and patron saint of cutoffs.
Way #60
With a ladies-who-lunch jacket, to balance your casualness with some polish.
Way #61
Like this DKNY look: longer, so they feel more fashion-y.
Way #62
With an oversized button-down untucked, so you can just barely see a glimpse of shorts underneath.
Way #63
Like Lucky Community member Noir, who's totally ready for any and all summer music festivals.
Way #64
With glamorous, over-the-top-in-a-great-way earrings.
Way #65
Like this street style star, who makes sneakers, shorts and a t-shirt look fashion-y.
Way #66
In camo, to mix it up a bit.
Way #67
Like Elizabeth Olsen, who makes us wish we wore more hats.
Way #68
Like this Isabel Marant model: with a vest. It's very "I'm with the band."
Way #69
With sequins, because why not?
Way #70
Like Lucky Community member Cara McLeay, who keeps it girly up top with a pink tweed shirt.
Way #71
With an interesting detail at the hem. (Super-easy to DIY, if you can't find a pair like these.)
Way #72
Like Victoria's Secret Angel Candice Swanepoel, who makes a muscle tee look amazing. (That dog's a pretty great accessory, too.)
Way #73
In a fun print that's not too loud.
Way #74
Like Maria Menounos: as a cover-up for your bottom half only.
Way #75
With patchwork denim, for a fresh spin on the denim tuxedo.
Way #76
Like this Twenty8Twelve model: with a wrap-front blouse for an airy outfit ideal for way-too-hot summer days.
Way #77
With floral embroidery that you'll want to get up close to to check out.
Way #78
Like Lucky Community member Chezka, who mixes a sporty bomber jacket with girly pink shorts.
Way #79
With something, anything leopard.
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.
Way #81
With opaque black tights, when it's too cold to go bare-legged.
Way #82
Like this model, who has the best slouchy-cool proportions going on.
Way #83
With a floppy hat, for a picnic in the sun.
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.)
Way #85
In a punchy pattern, like these preppy windowpane checks.
Way #86
Like Lucky Community member Nik G., who's got a good mix of girliness on top and swagger on bottom.
Way #87
With a striped shirt Taylor Swift would love.
Way #88
Like Erin Wasson, in her white-on-white-on-white fierceness.
Way #89
As a bermuda short, which can actually be really flattering.
Way #90
Like Lucky Community member Brittany Olson, who keeps it classic with her black and white palette.
Way #91
Like this DSquared2 model, except maybe a little more toned-down.
Way #92
With a chunky sweater, to keep you warm during a nighttime beach party.
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.
Way #94
With aviators, of course.
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.)
Way #96
In an unexpected color, like pale brown.
Way #97
With a pajama top, for a eclectic, nonchalant weekend look.
Way #98
Like Camilla Belle, with an eyelet top and sleek high ponytail for a look that's more on the polished side.
Way #99
Black and floral, so they're a little tough but also feminine.
Way #100
Like Lucky Community member Bindi Singh, whose dip-dyed ones are a notch more interesting than basic blues.