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12 Stylish Ways to Wear High Top Converse Sneakers

How to wear the ubiquitous shoe of cool.
12 Stylish Ways to Wear High Top Converse Sneakers
IMAGE INSTAGRAM/idaandu, pressmanissa
How to wear the ubiquitous shoe of cool.

The Converse All-Stars are the anti-fashion fashion sneaker that is sitting in every girl’s closet. What makes the shoe so cool is that the design is literally timeless with the look barely changing since its 1917 debut–that’s 102 years!

It was the first athletic sneaker ever made and in 1921 with the help of semi-professional basketball player turned Converse salesman, Chuck Taylor, the All-Stars became the go-to shoe for athletes and even the military during World War II. To honor Taylor’s effort and marketing genius, Converse added Taylor’s signature to the shoe. It became the first celebrity endorsed shoe and are now known as Chucks or Chuck Taylors to generations of rebels.

Jumping from athletic wear to streetwear All-Stars have since been a status symbol of cool and American counter-culture. From rockstars like Kurt Cobain to former U.S First Lady Michelle Obama, it transcends styles and looks good on everyone. To prove that we’ve curated style tips from these It girls below. See how they style their Converse high top sneakers their way!


Wear them with a flirty sundress.

Sundresses are the summer staple every girl needs in their closet. They’re feminine, cool in the heat, and a one-step outfit that looks so chic. Pairing it with high top Chucks adds a tomboy contrast that will make your outfit look less like you raided your grandma’s closet and more like you raided super model Kaia Gerber’s closet.

Cropped pants are your best friend.

Take a cue from Miss Universe Philippines 2014 Mary Jean Lastimosa and wear cropped pants that just hit above the top of the sneaker. They give balance to the high ankle upper and will give you a fire OOTD! We love Mary Jean’s high waisted jeans, fanny pack, and tube top look with her classic white Chucks!

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Look effortless in a shirt dress.

High top sneakers emote lowkey cool so why don't you match that effortlessness like Malia Obama with a chambray shirt dress? It has that cool college girl vibe that looks like you haphazardly put it together but ended up looking amazing. If you want to be more modest add some denim shorts or on-trend black biker shorts to your look. 

Wear them with wide-legged culottes.

If you didn’t think wide-leg culottes would look good with Chucks think again because blogger Ida Anduyan’s OOTD is making us rethink everything we thought about culottes before! Take note from Ida and pair yours with a T-shirt knotted at the most narrow part of your waist to show off your shape, denim overshirt, and sunnies. It’s an unexpected streetstyle combo that’s perfect for sightseeing or taking the perfect Instagram photo!


Channel your inner Sporty Spice.

Chucks are originally an athletic shoe, so lean into Converse’s sports heritage for this one. Why don’t you pair your Chucks like Bea Marin with an oversized windbreaker, crossbody purse, and on-trend biker shorts? You’ll be ready for a run or an impromptu photoshoot with friends. But here's a tip: Juxtapose the super sporty look with a polished beauty element (like a bold red lip or sharp eyeliner) for a more dressed up vibe.   


Wear an artsy outfit.

If casual isn’t your style then go for an artsy look! Try wearing an avante-garde piece to elevate a casual street look. Pairing something high fashion with your Chucks will make your outfit look less like a costume and more like you just stepped off the streets of Paris Fashion Week. 


Bring up the street style cred in a jumpsuit.

Why don’t you switch your everyday jeans and wear a tomboy jumpsuit instead? We love how Bea Marin wore a chic minimalist jumpsuit and cat-eye sunglasses with her high tops. It’s a put together look that’s great for work or happy hour with friends!


Wear an off-the-shoulder tunic and board shorts.

Remember when dresses over jeans were such a thing back in the 2000s? With the 2000s trend looming, bring back the look but reimagined for Gen Z. We love this idea from ASOS reinterpreting the aughties look by pairing Converse high tops with an off-the-shoulder dress over denim Bermuda shorts!


Wear yours as an after beach cover-up.

Channel your inner Venice Beach skater and wear your sneakers after a day at the beach! We love these after-beach outfits like Issa Pressman who paired her navy high tops with a bikini top and matching high waisted cropped trousers.

Or take a cue from blogger Rahnee Bransby who wore a bikini top and cuffed denim overalls with her high tops. They’re easy looks to wear after galavanting in the sand. Just make sure to wear your Chucks after you leave the beach unless you want to feel sand in between your toes–and not in a good way! 


Pair with a party dress.

Who says you can’t wear sneakers to a night out? Break the fashion rules and dress down a party dress or skirt with a pair of Chucks. We love how Pia Wurtzbach wore hers with a vinyl ruffle mini skirt and a silky button-down shirt or blogger Kaesha Ann Grauag in a bodycon dress. It adds a comfy-cool vibe to your look and allows you to properly dance the night away without worrying if you’ll fall on the dance floor!



Wear them baggy.

Jump on the '90s baggy jean trend Like Ida Anduyan! Rolled up at the hem, cropped or cut off it gives an effortless streetwear vibe. We love how she paired her Converse with a bucket hat, spaghetti strap top, and rolled up baggy jeans.

Slip into a silky slip dress.

Satin slip dresses are everywhere this summer so why not contrast the sturdy canvas All-Star sneaker with slithering satin? We love how Rihanna wore her sneakers with a slinky slip dress and a bucket hat for a chill street style look.


Or take a note from blogger Marie Von Behrens and wear a leopard silk skirt with a basic tee tucked in at the waist. You’ll be an Instagram hit every time. 

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