Every year, there’s a brief window when getting dressed turns into a daily guessing game. A crisp morning can give way to a warm afternoon, and it’s not unusual for an 80-degree scorcher to suddenly turn chilly by 4 p.m. But with the right transitional pieces—starting from the ground up—you can stay stylish and comfortable. Whether it’s the summer sandals you love or the new boots you’ve been saving for fall, these in-between days are the perfect opportunity to get creative with your footwear.
It’s also a great time to shop for shoes, with endless possibilities and no style off-limits. This season’s standout trends include colorful sneakers, bright white kicks, and the Zendaya-approved “sneakerina.” You can dress up with pointed-toe pumps or embellished ballet flats, or keep it classic with loafers or boat shoes. Boots are already on our radar for next season—think moto, western, and suede ankle styles—but don’t pack away your sandals just yet. From trusty flip-flops to chic heeled pairs, your summer favorites still have plenty of wear left. Check out our top picks below, and take inspiration from street style for how to wear them in the coming weeks.
The Loafer
Nothing says back-to-school nostalgia like a fresh pair of fall loafers. We’re especially loving driving loafers right now—minimalist with ruched seams—in everything from rich suede to glossy patent leather. Wear them with or without socks; a great loafer adapts to any mood.
The Flip-Flop
Ubiquitous this summer, flip-flops are still going strong as cooler weather sets in. Paired with long jeans or trousers and a light jacket, this laid-back style works for any temperature. Given how much use we’re still getting out of them, we’d call our summer flip-flop buys some of our smartest investments.
The Boat Shoe
If you haven’t tried boat shoes yet, now’s the time. This Miu Miu-approved style is perfect for transitioning into autumn. You can’t go wrong with Sperry, the brand that invented the boat shoe, but we’re also loving versions from Bally, Jamie Haller, and Tory Burch’s new “Boaty.”
The Heeled Sandal
Elevate your sandal game with a heeled pair. Whether it’s a strappy design from Khaite or Jil Sander, or a sleek thong silhouette from Toteme or A. Emery, a heeled sandal is a sophisticated investment—especially in classic black. Just add tights to wear them well into cooler days.
The Pointed Pump
The ultimate in ladylike footwear, a pointed pump instantly adds elegance to any outfit. Paired with everything from jeans to dresses, it’s a timeless staple that never goes out of style.From denim and trench coats to chic suiting, kitten heels from The Row and Toteme offer timeless appeal, while Toteme and Le Monde Beryl feature modern sculptural shapes—all perfectly on trend.
The Pop of White
We’ve long loved pops of red, but lately, optic white has caught our eye. It delivers the same effortless impact as any vibrant color, whether you’re wearing neutrals or a bold, colorful look.
The Statement Flat
Flats have gone glam, with bold prints, rhinestones, and studs turning the ballet flat into a standout piece. Gucci combines netting, straps, and square toes, while Valentino goes wild with leopard print. Christopher Esber’s rhinestone-dotted mesh style and Aeyde’s studded Mary Janes add even more flair.
The Moto Boot
Nothing beats the cool factor of a sleek, hardware-detailed moto boot. This season offers plenty of choices, from Paris Texas’s classics to Miu Miu, Khaite, and Chloé’s runway-ready styles. A slouchy pull-on pair works just as well with a summer dress as it does in rain or snow.
The Retro Sneaker
Scandinavian street style stars at Copenhagen Fashion Week proved sneakers go with everything—from airy dresses to printed pants and preppy polos. You don’t need to bike everywhere to appreciate their comfort and versatility. This season, retro sneakers get an autumn update with earthy tones and suede details.
The Western Boot
Cowboy boots are still going strong this fall, whether you prefer distressed, embroidered styles or sleek knee-high versions. They’re a must-have for transitional dressing.
The Sneakerina
Celebrity-approved and nostalgic (you might remember them from the early 2000s), the sneaker-ballet hybrid made a bold comeback this year. Striking a perfect balance between sporty and feminine, they’re as cool as they are comfortable. Wear them with dresses or workout gear.
The Clog
When in doubt, slip them on and go! From minimalist suede styles by A. Emery and The Row to hardware-embellished designs…From Chloé and Birkenstock, these versatile mules are perfect for quick morning coffee trips or evening strolls after dinner (just pair them with chunky socks if it gets chilly!).
Chloé
Jeannette leather clogs
$1,050 at NET-A-PORTER
Birkenstock
Boston rivets clogs
$175 at NORDSTROM
The Row
Hugo suede mules
$1,050 at BERGDORF GOODMAN
Photographed by Acielle / StyleDuMonde
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The Ankle Boot
Rich brown suede is everywhere this fall—from jackets and handbags right down to footwear. The soft material makes for a great pair of boots. The Row’s classic zip-front style gets a delicious update in chocolate suede, while rustic designs from Gucci and Gianvito Rossi are ideal for an early autumn cabin escape. Khaite’s “Marfa” boot adds a polished downtown twist to the Western style.
Gucci
Horsebit ankle boots
$1,320 at GUCCI
The Row
Zipped boots
$1,490 at THE ROW
Gianvito Rossi
Ripley ankle boots
$1,395 at NET-A-PORTER
Khaite
Marfa ankle boots
$1,480 at KHAITE
Frequently Asked Questions
Of course Here is a list of helpful and naturalsounding FAQs about transitional shoe styles for the shift from summer to fall
General Transitional Shoe FAQs
Q What exactly is a transitional shoe
A Its a versatile shoe designed to bridge the gap between two seasons For summertofall its a style thats lighter than a boot but more substantial than a sandal perfect for cooler mornings and warmer afternoons
Q Why cant I just wear my summer sandals or winter boots
A You can but transitional shoes are specifically designed for the unpredictable weather of early fall They offer more coverage and warmth than sandals but are more breathable and less bulky than heavy winter boots keeping you comfortable all day
Q What are the most important features to look for
A Focus on three things coverage material and versatility
Beginner Questions
Q Im new to this Whats the easiest transitional shoe to start with
A A classic loafer or a simple slipon sneaker Theyre incredibly easy to wear match almost everything in your wardrobe and are a clear step up from flipflops
Q Can I still wear opentoed shoes in the fall
A Absolutely Peeptoe booties and strappy blockheel sandals are great choices The key is that the rest of the shoe offers more coverage and structure making them feel seasonally appropriate
Q Are sneakers okay for fall or are they too casual
A Sneakers are perfect Opt for leather or suede styles instead of mesh athletic ones Fashion sneakers in neutral colors look chic with everything from jeans to midi dresses
Q What colors are best for fall transitional shoes
A While you can wear any color neutrals are most versatile Think taupe burgundy olive green cognac black and navy These colors easily complement common fall clothing palettes
Advanced Styling Questions