I Styled 5 Killer Under-$250 Outfits (to Prove It Can Be Done)

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As of this second, please do not come at me claiming that the coolest outfits always cost a small fortune. I've gone and put together five excellent ways to strategically spend a $250 budget, and I'm not cutting corners: I'm talking legit head-to-toe looks complete with stylish, comfortable shoes, really good bags, on-trend jewelry—the whole shebang, all for under $250. It can be done.

If you're trying to save some coin, or are a big fan of outfits that look great with white sneakers, or are just in the mood to scroll some new cool things while you're on the part of the subway that gets Wi-Fi, Boy George, have you come to the right place! (And on behalf of both your summer wardrobe and your credit card statement, we're so happy you're here.)

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OUTFIT TOTAL: $238

Here's your shortcut to looking easy, breezy, and super elevated. Head-to-toe neutral outfits are a whole big thing this year, and they're definitely the easiest way to look cool in a way that your parents "get." Take a chic white top (this season, we're accepting all forms of statement sleeves, button-downs, classic tees, and racer-back tanks), grab a mandatory pair of fresh white sneakers, and add a tailored trouser in between. Then it's just about the on-trend details that make everything look expensive: These under-$100 pants from The Frankie Shop come complete with such a good croc-effect belt. A structured top-handle bag always feels put-together, and a braided straw sun visor is so wonderfully '90s-sitcom-mom-on-vacation I can hardly stand it.

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OUTFIT TOTAL: $241

Wearing a bunch of brown might not sound super cute, but I'm very into all these deep warm hues, from the rust-colored dress to the tortoiseshell eyewear to the beaded wood bag. If you're a slip-dress aficionado, it's definitely time to get on board the knit-dress train—they're best paired with flat footwear for a modern vibe that suggests you're probably very cool but also super easygoing. On that note, these summer-ready off-white canvas Keds are definitely my pick for the best sneakers out there under $100. Oh, and this single statement earring from my favorite Danish-Irish jewelry designer, Maria Black? A bargain at $86, and therefore proof that you can find very cool things on NET-A-PORTER for less than the price of your first car.

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OUTFIT TOTAL: $183 

Shorts suits! Very important. Relaxed tailoring is so good with canvas slip-on sneakers, and adding these layered gold chains and a bamboo-handle purse means everything looks way more expensive than the sum of these price tags. One note: I purposely didn't include a little top here, partly for the whole five-items-per-collage continuity, and partly because one could argue this blazer look doesn't require one—but mostly because I instead would like your brains to marvel at the possibilities. A bright red ribbed tank? A black silk cami? A simple white tee? A button-down that adds more clashing (yet wonderful) stripes? Even if you don't already own them, any of these possibilities can be yours, thanks to the grand total of $67 I left in this $250 outfit budget. Go wild.

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OUTFIT TOTAL: $248

Investing in a long, summery printed skirt (in a color you love and that you can dress up or down) really is a thing that's worth doing—whether you consider $90 an investment or a steal is really your call. This elevated designer logo tee is the best shade of green, and it rings in at just $77. It has very good Frenchie vibes, as do these classic white Keds leather lace-ups (leather sneakers for $50 quite frankly deserve a special mention). If you're into more accessories that are acutely on trend, a beaded mini bag in sunshine hues plus these little shell earrings will get you across the finish line with $2 to spare.

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OUTFIT TOTAL: $248

Whether you're on vacation or just brunching like you are, off-duty cool is easily achieved by remembering the three S's: sneakers, stripes, and statement earrings. If this season has one clear message, it's to have some fun with your jewelry, for crying out loud! It doesn't have to be parrots (although parrots are encouraged); please feel free to insert the creature of your choice. If you usually live in jeans, these pastel-pink babies from Zara are lighter than denim and have some stretch, and they're very much ready for you to wear them all season. Cult Gaia bags are also still a thing, and this one is under $100, which means it's obviously selling out, but you can still get it at Saks (where it also comes in black, if you're that way inclined).

Natalie Cantell
Executive Director, Brand Studio

Natalie leads the style direction for the all content we create in partnership with our friends at various brands plus the legendary team of editors who work on those shoots and stories. She loves collaborating and storytelling, so it's a really fun role for her. It's also the first full-time job she's ever had⁠! She started out in her career as a very mediocre model who agreed to her first styling job to impress a photographer she had a crush on, which led her down a happy path of contributing to Vogue Australia and working as a stylist, fashion writer, and creative director for all sorts of brands and titles. She has a bachelor of communications, but most of her career opportunities came up thanks to some fleeting and accidental street style moments. She's been at Who What Wear for three and a half years and still loves to work as a freelance consultant with brands and designers to shoot their campaigns in NYC. She's originally from New Zealand, and Bondi Beach is her second home, but like just about every other 20-something, she fell in love with New York at some point. She lives in Williamsburg with her fiancé and their weird little dog, Ruby. If you ever need reccies for feel-good fashion, legit coffee spots, politics podcasts, or non-intimidating yoga studios, she's very much your girl.