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Peanut butter and jelly. Sunsets and rosé. Brangelina. Some things are just better together. 

The same is true when it comes to fashion. Certain items in your closet just work better with others. And for good reason: Classic style pairings stand the test of time because they complement each other and help answer that age-old question, “If I were to run into my ex wearing this outfit, would they kick themselves with regret?”

Ahead, we show you fashion’s must-own pairs that you probably already own (and if you don’t, it’s high time you do). Plus, we introduce a new “wild card” to complete each look in a way that’s unexpected and fresh.

Stripes Crossbody
Brit + Co

THE PERFECT PAIR: Striped Shirt + Leather Crossbody Bag

THE WILD CARD: Floral-Print Skirt

Breton stripes and a cognac-hued bag put a little New England class into your wardrobe. Add a flared floral skirt to look more like a lady, less like a sailor.

Kule top ($98)
Coach crossbody ($155)
Halogen skirt ($55)

SkinnyJeans Blazer

THE PERFECT PAIR: Blazer + Skinny Jeans

THE WILD CARD: Statement Scarf

Your casual-Friday uniform just got a whole lot cozier, thanks to the addition of a luxe, oversized scarf. Swap out your neckwear from season to season (think rich plaids for fall, silky florals for spring) all while keeping the backdrop sleek and basic. 

Zara blazer ($70)
Madewell jeans ($128)
Echo scarf ($41)

LBD Heals

THE PERFECT PAIR: LBD + Strappy Sandals

THE WILD CARD: Denim Jacket

Your LBD and party heels have seen you through countless cocktails and endless desk-to-dinner events. Your denim jacket has accompanied you to every baseball game and brunch. Put them all together: It’s a sophisticated but cool trio.

Calvin Klein dress ($90)
Joie sandals ($158)
Levi’s denim jacket ($78)

PencilSkirt Pumps

THE PERFECT PAIR: Pencil Skirt + Pumps

THE WILD CARD: Graphic Tee

God bless optical illusions in fashion: Pointy-toe pumps elongate your legs, while apencil skirt makes you look oh-so-Beyoncé. Add a bold graphic tee (you have permission to break out that Led Zeppelin World Tour 1971 number) and you’ve bagged yourself the coolest Saturday outfit ever.

Banana Republic skirt ($90)
MICHAEL Michael Kors shoes ($160)
NSF tee ($125)

Chambray Necklace
Gurl

THE PERFECT PAIR: Chambray Shirt + Statement Necklace

THE WILD CARD: Cropped Sweater

Not too fussy, not too stiff, with the right amount of ease plus polish: Boy, do we love a good chambray shirt. It's also the perfect backdrop for a less-than-subtle necklace. Layer like a pro and top it off with a cropped sweater to create pretty proportions.

Anthropologie shirt ($88)
BaubleBar necklace ($68)
Ann Taylor sweater ($20)

Fedora Buttondown

THE PERFECT PAIR: Button-Down + Fedora

THE WILD CARD: Palazzo Pants

Menswear is perennially chic (and so, so comfy), especially when it’s an oversized shirt topped off with a kicky hat. Keep the vacation vibe going with decidedly feminine breezy pants.

H&M shirt ($25)
Eric Javits hat ($250)
TopShop pants ($75)

PolkaDots Redlip
Anthropologie

THE PERFECT PAIR: Polka Dots + Red Lips

THE WILD CARD: Overalls

Polka dots and a berry-stained pout always read as timeless (and nod to the Audrey Hepburn era of playful glamour). Make it modern with slim-cut overalls, and then keep the look out of Minnie Mouse territory with grown-up sunglasses and a neutral clutch.

Jones New York blouse ($59)
Nars lipstick ($32)
Whistles overalls ($230)

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