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The Insider Pick:
With tons of incredible sneakers on the market, it’s hard to narrow down your options. If you have to choose just one pair, make it the Allbirds Wool Runners. They’re comfortable, chic, and so convenient.
I used to be That Girl — the one who thought high heels were the only “fashionable” shoes. It took, oh, about twenty years of blisters and aching toes before I finally realized how ridiculous I was being. There’s nothing stylish about trailing behind a group of your friends because the stilettos you’ve had on since 9 a.m. are slicing into your ankles like some "Game of Thrones" torture device.
Now that I’ve fully embraced the sneaker, my feet have never been happier. The right pair of sneakers can look amazing with so many different looks, from trousers to dresses. Best of all, they literally save you from a world of hurt.
What constitutes a “stylish” sneaker will surely depend on your individual style. But, by and large, the options on this list are easy to wear with many different outfits, comfortable enough to commute in, and won’t give you flamin’ hot blisters whenever you have to walk longer than a mile.
Here are the best stylish sneakers you can buy:
- Best sneakers overall: Allbirds Women’s Wool Runners, $95
- Best sporty sneakers: Adidas Women’s Stan Smith Shoes, $75
- Best classic sneakers: Converse All-Star Canvas Low Top Sneaker, $50
- Best non-sneakers: Everlane's Leather Street Shoe, $145
- Best patterned sneakers: Keds x Rifle Paper Co. Champion Lively Floral, $60
Read on in the slides below to check out our top picks.
The best stylish sneakers overall
Why you'll love them: Allbirds' cult-favorite Wool Runners are the kind of shoes you never really want to take off because they're simple enough to wear with most anything, comfortable enough to take to the gym, and machine washable.
Allbirds claims to offer “the world’s most comfortable shoe” and, from all the glowing reviews I’ve read online and heard in real life, they might be onto something. The brand’s initial product, the Wool Runners, are like a traditional runner’s sneaker only made of wool. I know, your feet are sweating just thinking about it.
But don’t let this unconventional detail throw you — people love these sneakers. Allbirds uses Merino wool from New Zealand that they claim is “temperature-regulating and moisture-wicking, all without an irritating scratchiness” for the Wool Runners. So, no, this isn’t the footwear equivalent of an itchy Christmas sweater.
The Allbirds Wool Runners are revered by comfy footwear experts. PopSugar Fitness editor Dominique Michelle Astorina described them as “incredibly soft, lightweight, and breathable, making for exceedingly comfortable wear” and insisted they didn’t smell funky even after a few wears sans socks.
She did note, however, that despite the name, “they're not quite suited for running,” so keep that in mind if you’re a hard-core jogger. On the flip side, the Insider Picks team also gave the Wool Runners top marks for comfort and convenience, so it seems the positives outweigh the negatives with these sneaks.
My favorite detail? These shoes are machine washable. Yep, you can toss ‘em in the wash to keep them looking fresh, which is especially awesome if you’ve got your eye on one of the lighter shades.
Pros: Moisture-wicking, machine washable, Merino wool helps control temperature and odor, moves with your foot
Cons: Not a hardcore exercise shoe
Buy the Allbirds Wool Runners for $95
The best sporty sneakers
Why you'll love them: Adidas’ Stan Smiths are an enduring hit because they go with everything. Floaty dresses? Check! Jeans and a sweater? Double check!
You can spot a pair of Adidas’ Stan Smiths from a mile away, especially in the unmistakable white and green colorway (though there are other options) and with the perforated side detailing. They don’t seem like they’d be the most versatile shoes in your wardrobe, and yet I think you’ll find they go with more outfits than you’d imagine.
Stan Smiths have been around since the 1970s, but they don’t look dated in the least. They have a slightly vintage look, but if they’ve basically been cool for forty years, I’d say these make a solid investment. Plus, at $75, they won’t totally break the bank.
The women’s Stan Smiths have 310 reviews on the Adidas website and come recommended by 92% of shoppers. One fan writes, “I love these shoes, they're so comfortable and they look very nice on; however, I recommend you go down a full size or half size because they fit very large since they're based off of a men's shoe design.”
Indeed, the men’s version is extremely similar and boasts almost 4,000 reviews, the majority of which give the kicks 5 stars. Although the aforementioned green and white version is probably the most iconic, the shoes come in several other colors.
Pros: Iconic design, comfortable, perforated side detail for temperature control
Cons: Reviews on the women’s shoe suggest sizing down
Buy Adidas Stan Smiths for $75
The best classic sneakers
Why you'll love them: If you wore Converse All Star Canvas Sneakers in high school, I have good news — they’re still cool!
Converse Chuck Taylor All Star’s were all the rage with a certain kind of teenager back when I was in school, and the All-Star Canvas Low Top Sneaker was the most iconic style. I never owned a pair myself, but I did “borrow” some that didn’t really fit me from a friend for a few months. Wearing them made me feel like a cooler version of myself.
Like Stan Smiths, Converse have never really gone out of style. They still might make you want to write Jimmy Eat World lyrics on the rubber soles and tell your mom that she just doesn’t “get” you, but hey, at least you’ll look cool doing it!
Besides, these shoes have history on their side. According to Complex, this style of Converse “has been in constant production since 1917, and has gone virtually unchanged since 1949.” They were initially popular with basketball players before becoming synonymous with the alternative music scene. Complex reported that, as of 2013, a pair was still sold “every 43 seconds.”
The Canvas Low Top is perhaps the most versatile Converse style and perhaps the most comfortable, too. 70% of the Amazon ratings give it 5 stars. One reviewer writes, “I LOVE Chucks. I have about 8 or 9 pairs. They are my go-to shoe. I wear them with everything., skirts, dresses, jeans ... I like them because they hold up well and are comfy right out of the box.”
Pros: Classic style that goes with anything, light canvas material, comes in a bunch of colors
Cons: Reviewers suggest adding an insole for additional arch support
Buy Converse Chuck Taylor All Star Canvas Low Tops for $50
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