6 Stylish Outfits for People Who Only Ever Want to Wear Sneakers

Sponsor Content Created With Steven by Steve Madden

I'd argue that fashion sneakers are the single best thing that's happened in the past 10 years. And not just in fashion—I'm talking across all possible life categories, and I'm barely exaggerating. As a bona fide flats wearer, the notion that women of decades past were expected to totter about in heels all day makes my (weirdly high) arches hurt just thinking about it.

We, thankfully, live in a glorious age of female empowerment (admittedly still a work in progress) where we can elect to wear slingback pumps on our own damn terms. Perhaps not coincidentally, the industry is trending toward taking luxury fashion off its pedestal, making it all much more wearable—and if it sounds like I'm practicing my argument defending the purchase of yet another pair of sneakers, well, I am.

All being said: Time for our seasonal sneaker outfit update! Inspired by the new Steven by Steve Madden line, here are six A+ outfits put together by our editors that capture their luxe-casual vibe for fall.

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WHY THIS OUTFIT?

When the New York winter hits, comfort really is the name of my game. I know there’s a high chance I won’t be removing my coat, so I want one that’ll serve as MVP among interchangeable basics and walkable, slush-defying sneakers.

WHERE SHOULD IT BE WORN?

Ideally while ducking into the back of a taxi where you can snugly watch the lights of the city pass by, preferably while traversing an iconic bridge. More likely, while trekking through the city streets ISO ramen.

BEST EXCUSE FOR A NEW PAIR OF SNEAKERS?

Monday, Friday, pay day.

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WHY THIS OUTFIT?

Because my heritage-print blazer is freshly dry-cleaned and ready for another busy season, plus red and pink is still my all-time favorite color combo. (Also, pearls are about to be a thing.)

WHERE SHOULD IT BE WORN?

In some kind of dark wood-paneled parlor with a big fireplace and enormous framed pictures of horses and greyhounds. Also, to the office.

BEST EXCUSE FOR A NEW PAIR OF SNEAKERS?

After repurchasing the same white kicks on repeat for years, I started to experiment with dipping my toes (eye roll) in a new hue each season. I surprised myself by thrashing a pastel-pink pair over spring/summer, and this rusty red feels just right for fall.

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WHY THIS OUTFIT?

Because you can never go wrong with a few standout accessories against an all-black look, especially when the temperatures start to drop.

WHERE SHOULD IT BE WORN?

Secretly practical footwear means you can wear this anywhere, really. Work, your favorite restaurant, to get coffee or run errands, to catch a movie, or to grab a drink. You get where I’m going with this.

BEST EXCUSE FOR A NEW PAIR OF SNEAKERS?

No excuse needed to treat yourself to something so versatile. I’m not necessarily a sneaker girl, but when I find a pair I really like, I’ll wear them over and over again.

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WHY THIS OUTFIT?

I like colder-weather dressing because my statement maker is always my coat and shoe combo. This plaid coat and embellished sneakers feels elevated but also easy to wear on those days where I don’t feel like trying too hard.

WHERE SHOULD IT BE WORN?

I’ll travel in this look during the holidays when I’m headed to NYC for a *real* experience of December weather. These sneakers are also perfect for getting through TSA without awkwardly having to tie and untie your shoes.

BEST EXCUSE FOR A NEW PAIR OF SNEAKERS?

You never need an excuse for a new pair of sneakers; keep stocking up!

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WHY THIS OUTFIT?

I like being comfortable and hate making decisions, so I tend to wear vintage jeans daily, along with some sort of black top and slip-on sneakers. It’s cozy and time-saving, but it’s also easy to amp up by way of bold, occasionally out-there accessories.

WHERE SHOULD IT BE WORN?

I might be outing myself as a decidedly not-fancy person, but I’d wear this just about anywhere… Especially on the weekends, when my plans tend to consist of walking to my local bookstore (hi, Book Soup) for the afternoon and then meeting friends for dinner in the neighborhood.

BEST EXCUSE FOR A NEW PAIR OF SNEAKERS?

No need for an excuse… I don’t buy sneakers all that often, so whenever I find a pair I like as much as this one, I jump on it!

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WHY THIS OUTFIT?

In L.A., we get to wear our fall dresses with sneakers instead of boots—no tights required. I promise I’m not trying to brag.

WHERE SHOULD IT BE WORN?

I’d wear this outfit on a weekend day after receiving one or two “what are you wearing?” texts from a friend before meeting for brunch. You know, the text that means I apparently am not allowed to show up to the new trendy spot in leggings and a sweatshirt. This outfit is secretly really cozy (thank you, sweaterdress!) and comfortable (thank you, sneakers!), but the accessories make it feel elevated enough to convince everyone I put in at least 90% effort.

BEST EXCUSE FOR A NEW PAIR OF SNEAKERS?

Excuse? I wear sneakers any chance I get and must own at least 10 pairs in various colors—but this is my first one in a brown shade, and I’m excited to work them into my rotation.

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Natalie Cantell
Contributing Fashion Editor

Natalie Cantell is an NYC-based style director, creative consultant, and contributing fashion editor. She was the executive director of Who What Wear and Marie Claire’s brand studio until 2023, and now freelances globally on shoots, stories, and special projects across fashion, luxury, beauty, home, and travel.