Transitional Shoes: What to Buy for Autumn-Winter

Person wearing a pair of BIRKENSTOCK Naples with white socks.

The weather’s confused. Your calendar says “autumn”, but your wardrobe’s still clinging to summer. Enter transitional shoes: your wardrobe’s MVP when the seasons are doing a bit too much.

Whether you’re dealing with morning chills, afternoon heat or an “is it going to rain again?” situation, these styles have you covered. From durable boots to autumnal trainers, here’s what to step into now and keep wearing through winter.

Person wearing silver New Balance 740s in the outdoors.

Best Transitional Trainers

Built for pavement, parks and everything in between: these are trainers that work harder when the weather gets weird.

That Y2K runner aesthetic? Still undefeated. The Nike P-6000 in white is both breathable but beefy enough for colder temps, ideal for layering with slouchy socks.

Throwback silhouette with autumnal tones = chef’s kiss. The New Balance 740 in white & burgundy is lightweight enough for all-day wear, yet chunky enough to not feel summery.

The adidas VL Court 3.0 in brown serves suede uppers and earthy tones, making it the ultimate cold weather shoe in disguise. Pair with wide-leg trousers and an oversized coat.

Go for a clean court vibe with subtle burgundy hits with the Reebok Club C Revenge in white & burgundy. Ideal for easy layering, jeans, cargos, wool socks… sorted.

Rugged retro runner vibes with a technical edge: meet the ASICS GEL-1130 in black & green. Built to handle whatever the day (or weather app) throws at you.

The KEEN Jasper Zionic in beige serves hiking energy but for everyday. Great grip, bold styling, and the durability of a trail shoe = outdoor girl era, activated.

Best Transitional Boots

When you need to level up the warmth without breaking into full winter mode.

A taller take on a classic, the Dr. Martens 2976 Hi Chelsea Boots in black are made for unpredictable forecasts. Waterproof-adjacent vibes with that signature DM stomp.

The Dr. Martens 2976 Leonore Boots in brown are lined with faux fur but still breathable: these are basically winter boots in a wearable autumn shell. Trust us, they’ll sell out.

Equestrian-coded and ready to go: meet the schuh Dory Riding Boots in brown. Pull on with leggings or long socks for that TikTok-approved “horse girl” chic.

Low-profile and ultra-versatile: we’re loving the schuh Dale Suede Chukka Boots in brown. These are the smart-casual dream shoe for cold-but-not-frosty days.

Cosy Favourites & Transitional Wins

These stylish picks are for when the temp drops – but you’re not ready for full snow boot energy quite yet.

The UGG Classic Ultra Mini II in dusted cocoa is the internet’s fave for a reason. Comfy, compact, and toastier than your morning flat white. The perfect autumnal shoes.

DM meets vintage Mary Jane with the Dr. Martens Buzz 8363 in brown, featuring a thick sole to handle slick streets. Wear with tights or chunky socks, depending on the mood.

Looking for something more transitional? Meet the Dr. Martens Zebzag Mule in black. Yes, they’re open-backed. But no, they’re not just for summer. Mules in autumn = peak transitional energy. Add thick socks and feel smug.

For another transitional win, look no further than the Birkenstock Naples in taupe. Suede upper + cork footbed + covered toe = comfort + cool. Whether you’re working from home or just hate laces, these deliver.