48 Transitional Footwear Options to Shop Ahead of Fall, from Khaite to Mango.

By Cortne Bonilla

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It’s the most wonderful time of the year, and no, it isn’t the holiday season just yet. More so, it’s the industry’s most anticipated season—when fashion month commences, the street style inspiration is abundant, and blistering temperatures conclude in favor of temperate mornings. For the fashion set, it’s also the ideal season for transitional dressing, from structured blazers atop cashmere T-shirts to lightweight trenchcoats layered over thin turtlenecks. Transitional footwear is an uncomplicated way to convert your wardrobe from midsummer to early fall, with tepid temperatures delivering ample opportunities to showcase a little ankle or a bit of kitten heel.

This season’s sought-after shoe trends feature a stimulating hodgepodge, yet they all embody a practical tone. Basically, all of our favored transitional footwear picks equip plentiful style without renouncing comfort, from minimalist pointed-toe pumps, sporty sneakers, embellished ballet flats, and a superb display of fisherman sandals. Set aside your lug-sole boots for now—these options should suffice.

Style du Monde

The once-modest shoe is now a must-have transitional footwear option, and we can thank Miu Miu for its resurgence. These ballet flats will inject a playful edge into your autumnal wardrobe, thanks to beloved styles from Aeyde and Loewe.

Loewe

bow ballet flats

MATCHES

Tory Burch

cap-toe ballet flats

TORY BURCH

Margaux

the Demi flats

MARGAUX

Mango

square-toe ballerina flats

MANGO

Loeffler Randall

Leonie ballet flats

NET-A-PORTER

Aeyde

two-tone ballet flats

NET-A-PORTER

Style du Monde

With a new season slowly creeping in, don’t give up the ease and comfort of a flip-flop, and instead, look to a pair of mules or slip-on flats. Designers like Khaite, Toteme, and Bottega are showcasing options that vary in silhouette, from sleek and sharp to square-toes.

Khaite

Otto 15 backless loafers

MATCHES

Massimo Dutti

leather mule loafers

MASSIMO DUTTI

Bottega Veneta

leather mules

NET-A-PORTER

Totême

satin mules

NET-A-PORTER

Zara

heeled mules

ZARA

Everlane

the leather mule sandals

EVERLANE

Style du Monde

Chic loafer options for women continue to ripen each season, and this year we’re eyeing an array of reinvigorated iterations, from classic penny leather (redone in a burnt brown hue) to nostalgic styles with a slight, walkable heel.

Hereu

Sineu leather loafers

MATCHES

G.H. Bass

Whitney Weejuns loafers

G.H.BASS

The Row

soft leather flat loafers

BERGDORF GOODMAN

Aeyde

Oscar loafers

NET-A-PORTER

Flattered

Sara leather loafers

MODA OPERANDI

J.Crew

Winona penny loafers

J.CREW

Style du Monde

Preppy style codes join forces with Parisian sensibilities to curate the most pleasing Mary Janes of now. From ultra-feminine to cool girl, the dainty shoe has been reimagined for the season with block heels, patent leather, and gleaming buckle embellishments.

Madewell

the Nettie heeled Mary Janes

MADEWELL

Carel

Kina Mary Jane trio pumps

NEIMAN MARCUS

By Far

Judy Mary Jane pumps

NET-A-PORTER

Larroudé

Blair block pumps

LARROUDE

Miu Miu

leather slingback pumps

MIU MIU

Roger Vivier

Très Vivier Babies pumps

MYTHERESA

Style du Monde

It’s safe to say that the kitten heel is officially back—the low-heeled styles have become a mainstay on the runways and in insiders’ wardrobes for the past few years. Comfortable and sophisticated, the kitten heel is ideal for work, play, and everything in between—especially when it comes to the styles donned by Prada and Saint Laurent this season.

Prada

Sculptural Floral kitten heels

SAKS FIFTH AVENUE

Zara

slingback kitten heels

ZARA

Valentino

VLOGO slingback pumps

NET-A-PORTER

Khaite

the Minna mules

KHAITE

Saint Laurent

Cherish slingback pumps

MYTHERESA

Miu Miu

coin penny loafers

NEIMAN MARCUS

Style du Monde

It’s clear that the caged-effect sandal obsession isn’t fading anytime soon—the style has gained an abundance of traction since it first popped back onto the scene two seasons ago. Fashion has spoken and the determination is obvious: your next investment should be a pair from Hereu, Marni, or The Row.

Marni

fisherman leather sandals

MATCHES

Hereu

Cabersa caged sandals

FARFETCH

The Row

fisherman sandals

SSENSE

Ancient Greek Sandals

Homeria fisherman sandals

MYTHERESA

Zara

flat fisherman sandals

ZARA

Dear Frances

Theo sandals

DEAR FRANCES

Style du Monde

Miu Miu’s thoughtful fall 2023 show proved that pumps are back, but they aren’t the pumps from yesteryear. Unlike the teetering 6-inch iterations of the past, the modern pump comes in various easy and sculptural iterations. The styling possibilities are endless: just picture these creamy Bottega’s peaking from beneath wide-leg trousers, or Prada's adding an unexpected twist to an otherwise neutral look.

Manolo Blahnik

Lista suede pumps

BERGDORF GOODMAN

Totême

the Sharp slingback pumps

MATCHES

Bottega Veneta

Comet Mary Jane pumps

MODA OPERANDI

Khaite

Marfa chain-detail pumps

FARFETCH

Prada

brushed slingback pumps

PRADA

Everlane

the Italian day heels

EVERLANE

Style du Monde

After the lockdown, it was clear that fashion lovers’ everywhere were more than ready to embrace comfort first, and sneakers became a shoe that isn’t gym exclusive. Who can forget the rise of Stan Smiths—worn during every Fashion Week and beyond? Now, there’s a transitional sneaker for everyone to wear with both suits and knitted maxi dresses alike.

Gola x Anthropologie

Elan sneakers

ANTHROPOLOGIE

Chloé

Lauren sneakers

MODA OPERANDI

New Balance

taupe 860V2 sneakers

SSENSE

Adidas x Wales Bonner

SL72 sneakers

MYTHERESA

Salomon

gender inclusive Speedverse PRG sneakers

NORDSTROM

Loewe

Flow Runner sneakers

SAKS FIFTH AVENUE