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

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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 Ballet Sauté 

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. 

Tory Burch

cap-toe ballet flats


square-toe ballerina flats

Loeffler Randall

Leonie ballet flats


two-tone ballet flats

Style du Monde

Slip & Slide 

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. 


Otto 15 backless loafers

Massimo Dutti

leather mule loafers

Bottega Veneta

leather mules


the leather mule sandals

Style du Monde

Loafin’ Around Town 

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. 


Sineu leather loafers

G.H. Bass

Whitney Weejuns loafers

The Row

soft leather flat loafers


Sara leather loafers


Winona penny loafers

Style du Monde

Mary Jane, Mary Jane 

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. 


the Nettie heeled Mary Janes


Kina Mary Jane trio pumps

By Far

Judy Mary Jane pumps


Blair block pumps

Miu Miu

leather slingback pumps

Roger Vivier

Très Vivier Babies pumps

Style du Monde

The Cat’s Meow

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. 


Sculptural Floral kitten heels


slingback kitten heels


VLOGO slingback pumps

Saint Laurent

Cherish slingback pumps

Miu Miu

coin penny loafers

Style du Monde

Fishy Business 

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. 


fisherman leather sandals


Cabersa caged sandals

Ancient Greek Sandals

Homeria fisherman sandals


flat fisherman sandals

Style du Monde

Pump It Up 

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


the Sharp slingback pumps

Bottega Veneta

Comet Mary Jane pumps


Marfa chain-detail pumps


brushed slingback pumps


the Italian day heels

Style du Monde

Sneaking Around 

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

New Balance

taupe 860V2 sneakers

Adidas x Wales Bonner

SL72 sneakers


gender inclusive Speedverse PRG sneakers


Flow Runner sneakers



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