Kourtney Kardashian has been in the spotlight for two decades, leaving us countless street-style looks to get inspired by. Here’s a walk through some of the greatest hits from her style files.

From the boho queen of Calabasas to rock royalty—she nails every look.

Reality star, mom, mogul, influencer: Kourtney Kardashian’s personal style has to tick a lot of boxes. Thanks to her innate sense of what’s cool, plus a long-time partnership with superstylist Dani Michelle, the TV personality has built an archive of outfits that inspire an entire generation (not to mention her 220 million Instagram fans!) 

With her tiny stature but larger-than-life personality, Kardashian has nailed the types of pieces that compliment and flatter her no matter what’s on the agenda in her highly-photographed daily schedule. From sizzling date night looks to airport dashes and matcha errands, you’ll see her reach for her favorites—including leather, leggings, vintage graphic t-shirts, and luxury handbags—time and time again.

Having been in the spotlight for two decades, there was no shortage of archive shots to choose from—here’s a walk through some of the greatest hits from Kardashian’s style files. 

Structured Suiting

Despite her petite frame (she’s a pint-sized 5’1) Kardashian doesn’t shy away from a power suit—like this black one with leather belt detailing across the legs for an appearance on The Today Show. 

Proportion Play

An easy, breezy go-to Kardashian look as of late is styling an oversized jacket as a dress, teamed with chunky platform boots to up the ante. It's a look that works double duty with coverage and just the right amount of a reveal.

Multi-tasking Mom

Out and about with daughter Penelope in Paris, Kardashian toed the line between chic and comfortable perfectly in opaque tights, loafers, and a tried-and-true mini dress and trench combo. 

Cool Girl

A vintage oversized Madonna t-shirt, animal print shorts, and tan boots make for a super chill grocery store run outfit in KK’s playbook. We’d be ready to crack open a beer too! 

Look of the day

Must see fits from all your favorite celebs. See the looks

Date Night

Kardashian’s style took a more daring turn when she began her relationship with now-husband Travis Barker, and the internet lives to see their all-black date night looks, like this strapless top and flared trouser ensemble complete with fuzzy clutch handbag to keep things interesting. 

Outerwear Game Strong

The humble trench coat is an MVP of Kardashian's rotation, whether she dresses it up with leather layers or tones it down for daytime. 

Monochrome

When she’s not in her favorite all-black, Kardashian often leans towards wearing one flattering tone from tip-to-toe, such as this serene pistachio outfit with a peekaboo sheer top underneath.  

Youthful Glow

Kardashian might be more than 20 years older than her friend Addison Rae, but the two look totally in sync in coordinated mini-length dresses, ' 90s-style sunglasses, and chunky boots while enjoying a Soho stroll—not to mention their matching matcha lattes.

Cinched

A maroon look head-to-toe is no easy thing to pull off, but Kardashian makes it look like a doddle—particularly with the use of an oversized belt to accentuate her figure.  

Killer Leather

We imagine that the black leather section of Kardashian’s wardrobe might just be an entire wing of her house by now. Still, no one does it better in glammed-up leather for the evening! 

Airport Cool

This jet-setting mom is never caught off-guard. Here she’s juggling it all, literally with her son Reign on her hip while cruising through a sea of paparazzi at JFK in style.

Elevated Basics

Stepping out for a TV appearance, Kardashian opted for some of her favorite pieces: a calf-length slim-fitting midi skirt, duster coat, knit top, and t-strap stilettos. Chances are, they’re hiding in your own closet waiting for you to recreate this outfit—Keeping up with the Kardashians, are we right?!

Dressed Up Denim

Why choose between your beloved leather and jeans when you can do both? Now that’s how you send pulses racing while in your daytime denim.

Sporty Spice

Elevating a pair of fire engine red track pants, Kardashian showed how to take things up a notch by pairing the tailored pants with a simple black vest and heels. 

Gone Clubbing

Kardashian headed to Up and Down nightclub in Manhattan, leaving her body-con dress at home in lieu of a crop top, bomber jacket, and leather pants instead. 

Shopping In Style

While filming Kourtney & Kim Take New York back in 2011 (were we ever so young?!), the eldest Kardashian sister was papped in a sophisticated polka dot pussybow blouse while indulging in some retail therapy. 

Off Duty Uniform

Take a shot every time you see someone in LA wear this outfit. Kardashian was instrumental in popularizing bike shorts, sneakers, and a designer carryall. Spoiler alert: you’re drunk!

Classic Rock

Why choose between a Birken and a band tee? Kardashian always manages to fuse her dueling style personalities with ease.

Cost Per Wear

The thing about Kardashian is once she gets her hands on an accessory—she’s not afraid to wear it. Case in point: the Celine Luggage Tote, which barely left her arms in 2012. She’s paired it here with a bohemian white lace blouse, skinny black pants, a double-row headband and tousled bun, and Cartier accessories. 

Cute Mama

Kardashian’s maternity outfits were always a slay. The now mom-of-four opted to draw attention to her bump from the get-go, like in this form-fitting dress and costume necklace she wore while pregnant with her first son, Mason, in 2009.