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People often think of Labor Day weekend as the unofficial sendoff to summer (a notion that Charli xcx recently confirmed when she took to X to announce the end of brat summer). And so, as the days wind down to autumnal equinox, and we welcome the return of fall fashion, it begs the question—what footwear should you sport when hitting the pavement?
From loafers to box-fresh sneakers to sandals that aren’t ready to be retired yet, Vogue editors are embracing the return of balmier temps with their favorite transitional shoe styles. Below, the pairs they plan to baby step into fall with.
Vogue Editors’ Picks:
The Fall-Friendly Sandal
“I love a grown up Birkenstock for September in New York City when it’s still balmy out but you want to lean into the fall mood in the air. I love these espresso leather ones with the hammered gold buckle, perfect for a playground run or the office!” —Chloe Malle, Editor, Vogue.com
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The Boat Shoe
“When the day comes for me to finally have to retire my A.Emery flip-flops, I’ll be switching into a pair of chocolate brown boat shoes from Bally. The style doesn’t feel too trendy nor too classic, which is something I’m always looking for in an investment buy. I went for the dark brown, it felt a little more exciting than black! —Talia Abbas, senior shopping editor
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The Velvet Thong Sandal
“I have been a devoted flip flop wearer all summer long and have been wondering what my fall equivalent will be. They’re just so easy and really look good with everything, especially a wide-leg trouser. To be honest I might milk it until it’s absolutely too cold to wear them. To be determined! I do have a a velvet pair that feels more appropriate for fall.” —Madeline Fass, senior shopping market editor
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The Wide Boot
“Recently I was home at my parent’s for the weekend and commuting directly to the office from their place. There I was, walking down the stairs, in my Schutz boots styled with a pair of jorts and oversized button-down, to which my mother exclaimed with earnest concern ‘You’re wearing boots? But it’s still technically summer!’ Ironically, I received countless compliments on that day, and most specifically on my boots. So yes, bring on the boots even before their prime!” —Conçetta Ciarlo, associate manager
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The Classic Keds
“I’m back on my Keds beat! They work for everything and people stop me all the time being like, ‘Keds! Nice!’ I’m walking to the Vogue offices skipping in the streets, wearing them all day, even customizing them (my favorite) for different looks.” —Arden Fanning, beauty editor at large
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The City-Approved Heels
“I think zipper details are such a great design element, and knew that I needed these slingbacks as soon as I saw them. They’ll be great with an A-Line midi skirt and a crisp white button-up. The second is a velvet platform in the perfect shade of brown. I’m very much aligned, and will be wearing these to the office, out to dinner, and everywhere else.” —Leah Faye Cooper, digital style director
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The Satin Flip Flop
“Possible hot take but I think the perfect transitional shoe is a leather flip flop. They look great with jeans or a maxi/midi skirt, with a jumper thrown around the shoulders for a chillier evening. It makes me feel like I’m at the beach for just a little longer—and still looks chic!” —Madeleine Schulz, Vogue Business reporter
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The Earth-Toned Boot
“The perfect fall transition shoe has to have one of three things: an earthy, fallen-leaf color, textured notes (think bouclé, leather, suede), and the ability to weather temperatures between 50 and 72 degrees. This Dico Julia boot from Danish brand Anonymous has all three. The light brown color is a great pitstop before the moodier, winter colors and the lack of hardware keeps the boot feeling sturdy, yet light. Though this shoe is to my taste, any moto boot will carry you perfectly through the upcoming fall.” —Maya Layne, entertainment associate
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The Mary Jane
“September and October are my favorite months of the year in New York City, and there’s no better shoe for those not-too-hot yet not-too-cold days than a Mary Jane! I recently snagged these Le Monde Beryl Mary Jane flats during an end-of-summer sale, knowing that I’ll be able to wear them well into the fall in New York City!” —Alexandra Ditch, commerce producer
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The Edgy Flats
“Transitional footwear is the unsung hero of seasonal style shifts, effortlessly bridging the gap between summer sandals and winter boots. My go-tos are my Tony Bianco lug-sole loafer, or Ganni’s pointed-toe buckle flats. They perfectly pair with layered looks, as the weather turns crisp!” —Rose Carlisle, special events assistant
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