How Our Editors Are Styling 8 Under-$40 Buys for Both Summer and Fall

Ready for some summer-to-fall styling inspiration? Our editors are a stylish bunch, no doubt about that, so today we're taking this opportunity to flex our styling skills to show you how to make the most out of your transitional wardrobe. Thanks to the versatile items from our own namesake clothing line, you're about to see how to wear key pieces for the current late-summer season and keep wearing them well into fall. If these aren't useful investments, then I don't know what are.

As a refresher, we drop new pieces for our Who What Wear line each month, and today, our editors are highlighting the flowy dresses and pretty prints from the August collection. Even though nothing rings up for more than $40, the cool looks our editors put together are making these affordable buys look far pricier. Ahead, see how we each wear our picks for both seasons and then shop our favorites if you're so inspired. (P.s. scroll to the end to check out some Zoom backgrounds we made inspired by the looks.)

Jasmine Fox-Suliaman, Audience Engagement Editor

"What I love about this dress, other than the fact the fabric is super breathable and the cut is über cute, is that it's super versatile. I live for a summer dress that can be styled up or down depending upon your plans—and this WWWC is just that. Whether you style it with a pair of sneakers for a grocery-store run or dressing it up with a pair of earrings and sandals for a socially distanced brunch situation. This dress exudes posh without the fuss."

Pictured: Who What Wear Puff Short Sleeve Ruffle Dress ($37); Mejuri Organic Pearl Hoops ($75); Missoma Gold Square Black Signet Ring ($123); Jeffery Campbell Khara Sandals ($75); Loeffler Randall Zadie Feather Circle Tote ($275)

"I'm not the hugest fan of pants, so I love dresses that can transition into the fall well, and I feel the puff-sleeve cut of this dress along with the print lends itself marvelously to doing just that. All you have to do is swap out your favorite sandals for your favorite boots, and you've got a fall-ready look with just one piece."

Pictured: Who What Wear Puff Short Sleeve Ruffle Dress ($37); Dr. Martens Jadon Platform Boots ($180); Urban Outfitters Rounded Rectangle Sunglasses ($20); Maison Miru Architect Hoops ($99)

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Allyson Payer, Senior Editor

"I got off pretty easy with this dress—it's so easy to wear in both summer and fall. Aside from being really comfortable and flattering, the one-shoulder style makes it feel so much more modern than your typical knit midi dress. You don't need much in the summer, just sandals and minimal accessories."

Pictured: Who What Wear dress; Loewe Small Basket Bag ($450); Staud Simone Mules ($265)

"For fall, you miss the full effect of the dress since the sleeves are probably going to be covered up, but it's still a great fall-friendly style, thanks to the color. I went with an oversize camel coat and knee-high boots, which I think give the dress an elegant look."

Pictured: Who What Wear Dress; Tôteme Annecy Coat ($1100) and Wide-Shaft Boots

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Kat Collings, Editor in Chief

"Soft pants are great. Soft pants that cleverly hide that they're soft pants and maybe even look like trousers? Stupendous. These fall into the latter category, as they look fancy enough for a big presentation (in the olden days when we participated in IRL meetings and anyone saw what you wore on your bottom half) yet feel as comfortable as pajama pants. The print has a vintage appeal too and is super versatile because it can go with black or brown (or olive as I styled it). I also love that they can dress up a casual tank yet somehow can still hold their own paired with a blazer. Basically, these pants are a win!"

Pictured: Who What Wear High-Rise Wide Leg Pants ($35); Goldsign The Rib Tank ($148); Neous Alkes Leather Sandals ($560); Monica Vinader Doina Chain Necklace ($275), Wide Chain Bracelet ($395), and Fine Chain Bracelet ($175)

Pictured: Who What Wear High-Rise Wide Leg Pants ($35); LVIR Belted Wool Blazer ($342); Rachel Comey Adams Sandals ($435)

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Anna LaPlaca, Associate Editor

This frock really impressed me. The puff sleeves and babydoll shape are so easy to wear and truly a major dress silhouette of the moment, which make this not only a practical option (hello, versatile midi length), but an on-trend one, too. While it's still summer, I'm leaning into the whole cottagecore aesthetic. I married it with a scarf headband and ankle-tie sandals.

Pictured: Who What Wear Puff Sleeve Tiered Babydoll Dress ($40); vintage scarf; Krewe Ward Sunglasses ($295); Amanu Studio sandals

While the voluminous shape makes sense for summer, I think I like this dress even better for fall. It lends itself super well to pairing with chunky-sole shoes, which just so happen to be a big fall trend since the wide-cut shape balances it out nicely. It's truly one of those throw-on pieces that speaks for itself (and it doesn't hurt that it's comfortable, too). 

Pictured: Who What Wear Puff Sleeve Tiered Babydoll Dress ($40); vintage sweater; Converse All Star Lift Cable ($85)

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Lauren Eggertsen, Senior Fashion Editor

"This dress has such a pretty print so I didn't want to distract from it, especially when extra layers are not necessary right now. A simple strappy sandal was really all it needed!"

"A snakeskin boot oddly paired so perfectly with this dress. I added the leather blazer to toughen it up a bit, but a simple black coat would also go perfectly."

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Sarah Yang, Managing Editor, THE/THIRTY

"I love that this dress is so simple and comfortable but you can really dress it up with some jewelry and heels, or down with some flats or sandals for everyday wear. Even though nights out aren't an option right now, I styled both my summer and fall looks for a night out or a special occasion. For summer, I paired with tortoiseshell-esque sandals from Zara, colorful earrings, and a bright and bold lip. I could see myself wearing this to cocktails and dinner with friends or a date night. While those things aren't really happening right now, I'll settle for wearing this dress to socially-distanced backyard drinks if I persuade my friends to ditch the house dresses and bike shorts!"

"I feel like I need to reiterate to everyone out there how incredibly comfortable and non-fussy this dress is, but how put-together it looks when you have it on. Seriously, it's one of those magical outfits that you throw on for an effortlessly dressed-up look. For the fall, I paired it with lace-up heels, a printed clutch, and simple gold earrings. I also did my hair in a relaxed bun for a more sophisticated vibe. I'm planning on re-creating this for my friend's Zoom wedding in October (and yes, I will even wear the heels!)."

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Judith Jones, Market Editor

"I love the bold, vintage-inspired print and silhouette of this puff-sleeve dress. Since it's a statement dress, it doesn't need too much in the way of accessories. This summer, I've been styling it with chunky black sandals, and when fall arrives I'll pair it with black knee high-boots and hoops. Bonus: The dress has handy pockets. Always a win in my book."

Pictured: Who What Wear Puff Short Sleeve Ruffle Dress ($37) and Axel Sandals ($76)

Pictured: Who What Wear Puff Short Sleeve Ruffle Dress ($37)

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Erin Fitzpatrick, Senior News Editor

"It’s super hot in Southern California, so I’ll be wearing this breezy puff-sleeve dress by the pool for the foreseeable future. All I need is a floppy hat to keep the sun off me and some sunglasses. Oh, and my dog, of course."

Pictured: Who What Wear Puff Sleeve Tiered Babydoll Dress ($40)

"For fall, I’ll be wearing this dress with my new & Other Stories bag. The brown suede and croc print feel very fall-like, so the bag tones down the summery-ness of the dress. Instead of sandals, I’d probably wear this dress with sneakers for fall."

Pictured: Who What Wear Puff Sleeve Tiered Babydoll Dress ($40); & Other Stories Suede Canvas Strap Crossbody Bag ($149)

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More summer-to-fall editor favorites:

Love these looks? Download our Zoom backgrounds inspired by them below:

Up next: 22 under-$40 buys that will 100% level-up our wardrobe.