6 transitional shoes that will see you through autumn/winter

And how to style them.
6 Transitional Shoes To See You Through AutumnWinter 2025
Jeremy Moeller

What exactly are transitional shoes? Well, this time of year is confusing weather-wise. You can leave your house in clothes meant for sunny weather, and get caught in a rainstorm. Or, even worse, you set out in a warm, cosy outfit, then progressively melt as the day goes on. For this awkward time, you'll need shoes that will carry you through a variety of scenarios.

To help alleviate the weather whiplash, we’ve studied the New York Fashion Week set to bring you the best transitional shoes, and how to style them. Since fashion month happens throughout September, it's a good time to observe how the pros are dressing.

Featured in this article

Willa Western Boots
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Mid Rise Straight Flare Jeans
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ASOS DESIGN Milan Chunky Chain Detail Loafers
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6 Transitional Shoes To See You Through AutumnWinter 2025
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Cowboy boots and a sweater dress

When the weather makes a turn for the worse but you still want to show off your legs, opt for a warm sweater dress on top and boots on bottom.

DIA Studios Cowboy Western Boots

Willa Western Boots

& Other Stories Knitted Mini Dress With Belt

Knitted Dress

6 Transitional Shoes To See You Through AutumnWinter 2025
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Sneakerinas and a trench coat

Two of the hottest items of the year – why not combine them? Ballet flats have ruled fashion for a while now, but sneakerinas, their sneaker-hybrid cousins, are more practical for the colder months.

Adidas Originals Taekwondo Mei Ballet Trainers

Speedcat Ballet Cow Print Sneakers

Camel Cape Trench Coat

Twill Trench Coat

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6 Transitional Shoes To See You Through AutumnWinter 2025
Jeremy Moeller/Getty Images

Wellies and a midi skirt

Wellies are essential for rainy weather, but who said being sensible has to be boring? Opt for wellies in fun colours, or match a more classic pair with a stylish midi skirt.

Hunter Original Short Wellington

Hunter Original Tall Leopard Print Wellington Boot

ASOS DESIGN Co-ord Hanky Hem Skirt

White Polka Dot Knee Length Slip Skirt

6 Transitional Shoes To See You Through AutumnWinter 2025
Christian Vierig/Getty Images

Knee high boots and long shorts

Long, baggy shorts combined with knee high boots is a win as the weather starts to get colder. It allows you to have fun with your silhouette, while keeping you warm.

UO Wine Kaia Knee High Leather Boots

ASOS DESIGN Charmed Heeled Knee Boots

Dark Denim Bermuda Shorts

Belted Wrap-Front Cotton Shorts

6 Transitional Shoes To See You Through AutumnWinter 2025
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Ankle boots and jeans

Your trusty jeans with a pair of ankle boots are the perfect formula for an autumn outfit that looks put together, but is the easiest thing to throw on.

Hedda Boots

Chloé Susan Short Ankle Boots

High-Waist Flared Jeans

318™ Shaping Wide Leg Jeans

ED Skylar Flare Jeans

Mid Rise Straight Flare Jeans

6 Transitional Shoes To See You Through AutumnWinter 2025
Edward Berthelot/Getty Images

Loafers and a maxi skirt

Loafers have been super popular this year, and they're not about to go anywhere. So match them with a maxi skirt – either in a pattern like check, or an eye-catching texture like satin – to carry this trend into the colder months.

ASOS DESIGN Milan Chunky Chain Detail Loafers

Temara Arcadia Leather Loafers

ASOS DESIGN Satin Bias Maxi Skirt

Black Checked Midi Skirt