There’s a small window each year where getting dressed becomes a day by day guessing game. A chill in the morning can mean shedding layers by noon, and it’s not unheard of for an 80 degree scorcher to transform into a cold snap by 4 p.m. It’s hard to miss a step (sorry, couldn’t resist), however, when you’re armed with the right array of transitional staples, starting from the bottom up. From the summer sandals you’ve grown quite attached to, to those cute new boots you’ve been eyeing for fall, these in-between days are the perfect chance to style your shoes in the most creative of ways.
Vogue’s Favorite Transitional Shoes
Featured in this article
The Studded Clog
Birkenstock Boston rivets clogs
See MoreThe Suede Ankle Boot
Gucci Horsebit ankle boots
See More
It’s also one of the funnest times to shop for footwear, as the possibilities are endless and no style is off limits. The statement makers of the season include colorful sneakers, a pop of optic white, and the Zendaya-endorsed “sneakerina.” You can polish up in pointed-toe pumps and embellished ballet flats, or keep it classic in a loafer or boat shoe. We have our eye on several boot styles (moto boots, western boots, and suede ankle boots all incoming) for next season, though no need to pack up those sandals just yet—from trusty flip-flops to chic heeled pairs, your summer MVPs still have quite a bit of mileage left in them. Shop our top pairs below, and take cues from street style on how to wear yours in the coming weeks.
Photographed by Acielle / StyleDuMonde
The Loafer
Nothing captures back-to-school nostalgia like a new pair of shoes for fall, especially if that pair is a preppy loafer. We’re loving a driving loafer lately (think minimal, with ruched seams) in every iteration, from sumptuous suede to patent leather. Styled with a sock or without, a great loafer is ready for whatever the mood calls for.
Dries Van Noten
patent crinkled-leather loafers
Photographed by Acielle / StyleDuMonde
The Flip-Flop
Ubiquitous this summer, the flip-flop is still going strong even as cooler fronts start sweeping in. Juxtaposed with ground-grazing jeans or trousers and a transitional jacket, the toe-peeping style is ready to take on any temp. Given the mileage we continue to get from them, we’re considering our summer flip-flop purchases one of our smartest investments.
Photographed by Acielle / StyleDuMonde
The Boat Shoe
If you haven’t snagged a pair of boat shoes yet, now’s the time! The Miu Miu-approved shoe is perfectly suited to transition your looks for autumnal temps. You can’t go wrong with a pair by Sperry, who invented and perfected the boat shoe, but we’re also obsessed with iterations by Bally, Jamie Haller, and Tory Burch’s newly introduced “Boaty.”
Photographed by Acielle / StyleDuMonde
The Heeled Sandal
Elevate your sandal game with a heeled pair, if you haven’t already. Be it caged and strappy like those at Khaite and Jil Sander, or a sleek thong silhouette like those from Toteme and A. Emery, a heeled sandal is a sophisticated investment—particularly in classic black. Simply add tights to carry your favorite pair into cooler days.
Photographed by Acielle / StyleDuMonde
The Pointed Pump
The ultimate mainstay in ladylike footwear, a pointed pump instantly ups the elegance of your day to day, paired with anything from denim and a trench to chic suiting. The Row and Toteme offer timeless kitten heels, while Toteme and Le Monde Beryl embrace modern sculptural silhouettes, all perfectly on point.
Photographed by Acielle / StyleDuMonde
The Pop of White
While we’ve been long time proponents of pops of red, a new color has caught our eye as of late: optic white. It offers the same low-effort, high-impact reward as any vibrant color, whether you’re wearing neutrals or a super-chromatic look.
Photographed by Acielle / StyleDuMonde
The Statement Flat
Flats have gone all out glam. From bold prints to rhinestone and stud embellishments (or all of the above at once), the ballet flat has claimed its place as a statement piece. Gucci marries several trends at once with a netted, strapped, and square-toed pair, while Valentino shows off its wild side in leopard print calf hair. Likewise, Christopher Esber’s signature mesh style dotted in rhinestones and Aeyde’s studded Mary Janes will have you tapping your toes.
Christopher Esber
Minette mesh ballet flats
Photographed by Acielle / StyleDuMonde
The Moto Boot
Is there anything cooler than a wind-slicked, hardware-heavy moto boot? We’re spoilt for choice this season, with options from the boot stalwarts at Paris Texas to the lived-in, runway-ready takes at Miu Miu, Khaite, and Chloé. A pull-on pair with the perfect slouch plays well with a summer dress for sunny days, yet is perfectly suited for any weather event on the horizon, be it rain, slush, or, dare we say the word… snow.
Photographed by Acielle / StyleDuMonde
The Retro Sneaker
Leave it to the Scandi street style stars of Copenhagen Fashion Week to make sneakers work with almost every outfit under the sun—from frothy Cecilie Bahnsen dresses to printed pants and preppy polos. You don’t have to be commuting by bike to embrace the agility (and comfort) that a sneaker offers. This season, retro kicks get an autumnal update in earthy tones and suede details.
Adidas Originals
x Wales Bonner Lo Pro sneakers
Maison Margiela
Sprinter leather and brushed suede-trimmed shell sneakers
Photographed by Acielle / StyleDuMonde
The Western Boot
Memories of dusty Coachella days and Cowboy Carter tour fits are far from fading, as the cowboy boot gets carried forward into fall dressing. Whether you put the wild in the west with a distressed and embroidered pair, or keep it more cowboy-chic in a streamlined knee-high pick, the Western boot is a transitional must-have.
Photographed by Acielle / StyleDuMonde
The Sneakerina
Celebrity-approved with throwback flair (perhaps you had an OG pair in the early aughts), the sneakerina made a bold entrée into our wardrobes this year. Striking a perfect balance between sporty and girly, the sneaker-ballet hybrid is as cool as it is comfy. Wear yours with anything from your most darling dresses to your go-to workout gear.
Adidas Originals
Taekwondo Mei ballet sneakers
Photographed by Acielle / StyleDuMonde
The Clog
When in doubt, slip on and go! From minimalist silhouettes in suede by A. Emery and The Row, to hardware-embellished options from Chloé and Birkenstock, these transitional mules are ready-made for morning coffee runs and post-dinner evening runs (just add a chunky sock if temperatures dip!).
Photographed by Acielle / StyleDuMonde
The Ankle Boot
Rich brown suede has officially taken over this fall, from our jackets to our handbags and right down to our toes; the supple material undoubtedly makes for a great pair of boots. The Row’s signature zip-front boot gets a yummy makeover in chocolate suede, while rustic pairs from Gucci and Gianvito Rossi feel prime for an early fall cabin getaway. Khaite’s “Marfa” style bring downtown polish to the Western boot.
