Converse

Jessica Hart might have been dressed down in a white tee, denim cutoffs, and high-top white Converse sneakers ($45) while walking her pup in NYC, but per usual the model managed to still look stunning. Her short shorts accentuated her gorgeous gams, while her lust-worthy locks peeked out from under her sporty red cap. Jessica finished her street style with an oversized watch, a few bracelets, and a black canvas backpack. Channel your inner model with a white tee, denim cutoffs, and her exact Converse for a low-key day at the park, or take a cue from Miley and work your high-top kicks with a floral dress.

If there's one thing the sneaker-obsessed can agree on, it's that there are some brands that defy fleeting trends and seasonality. To this point, there's no argument that Converse, Keds, PF Flyers, and Superga have stood the test of time without ever compromising a simple rubber-soled, canvas-top silhouette in the process. Perhaps, that's what makes these iconic brands — all synonymous with old-school laid-back style — a favorite for celebrities, sleek style setters, and everyone else you know. But as a devout sneaker classicist myself, I think the appeal of a high-top Chuck or a cherry red low-top Superga is deeply rooted in its history, its functionality, and its easy ability to evoke a nostalgic-meets-sporty vibe simultaneously.

A few of our favorite classic kicks spotted (clockwise from top left): Kristen Stewart, street style, Miley Cyrus, street style, Michelle Williams, street style, Jennifer Aniston, street style

Steeped in a rich Americana culture — save for Superga's Italian-bred beginnings — these household names have been around since the early 1900s. That is to say, it's entirely possible your grandparents were rocking the same kicks you are today. Maybe it's my memory of The Sandlot and the film's emphasis on PF Flyers — "guaranteed to make a kid run faster and jump higher." Maybe it's the fact that Keds can complete a plethora of looks, from girlie 1950s poodle skirts to Grease-inspired all-leather getups. Or maybe it's because when we think of Converse, we instantly are transported to the innocence of our playground days. Whatever it is that strikes a chord first, it's pretty evident that, like our striped t-shirt fixation, there's a real practicality that comes with wearing these classic sneakers. You can style them with something as casual as denim or as ladylike as a tea-length dress — either way, it's a no-fail look with an effortless feel.

Inspired by the stylish stars (picture above) that wear them, read on for updated classic kick styling tips.

Keira Knightley and Steve Carell's new movie, Seeking a Friend For the End of the World, opens this Friday, June 22, and while Keira's onscreen wardrobe isn't extensive, one of the outfits she wears throughout the flick is perfect for Summer. Here is Penny, Keira's character, sporting a lavender button-down, a knee-length dress with an army green anorak, black Converse sneakers, and a delicate gold starfish necklace. It's a simple look but one with a color combination that makes it fresh. We're smitten with the mix of lavender and army green and the fact that she looks cute yet relaxed in her sneakers. Before you catch the movie this weekend, get Keira's onscreen look by shopping similar pieces below.

Rihanna is no stranger to fashion-forward styles, but the singer really turned heads while shopping in NYC when she worked a soft pink American Apparel lace bandeau top ($18), a pink pleated Topshop skirt, black high-top Converse ($50), and a mini Céline tote. The midriff-baring starlet accessorized her ballet-meets-street style with oversized round Karen Walker shades ($250), a few necklaces, and diamond stud earrings, then layered on a two-tone sweatshirt. Style Rihanna's exact top, shoes, and shades with a flirty pleated skirt and laid-back hoodie to re-create this daring look.

While strolling through LAX airport, Nicole Richie worked a comfy and cool travel ensemble: plush black jacket, black skinny jeans, studded high-top Converse sneakers — get the black or cream pair with silver studs here ($175) — and House of Harlow accessories. It was the perfect combination of style and comfort, fusing basics with standout accessories like a textured House of Harlow bag ($506), blacked-out House of Harlow shades ($138), and an oversized gray scarf. Score Nicole's kicks to pair with your laid-back looks or work them with a sheer coral Zara maxi skirt ($80) and black tank for a glam-rock vibe.

While promoting their new flick Snow White and the Huntsman in Madrid, Kristen Stewart and Charlize Theron coordinated their all-black outfits down to their old-school Converse and Nike sneakers. We all know Kristen is a huge fan of comfy-cool sneakers, and we love how her red Converse Chuck Taylors ($50) livened up her dark outfit, which included her go-to quilted leather Balenciaga jacket and a black Joe's Jean tank ($88). As for Charlize, we're used to seeing her in edgy heels, so the black-and-white Nike low tops ($35) she wore were a refreshing change. Plus they lent sportiness to her otherwise-classic ensemble. Score Kristen's and Charlize's exact sneakers, then be sure to add them to your everyday outfits for a comfy-slash-sporty flair.