Party Heels Can Wait—I’ll Be Rotating These Classy and Comfy Boot Outfits Instead This Winter

COMFY BOOTS OUTFITS
(Image credit: Future)

In my opinion, there's nothing worse than an uncomfortable shoe. I'm not very patient if footwear requires me to layer ten plasters in order to wear them, which is why I'm always on the lookout for styles that won't take much breaking in. You may automatically think of flat styles when it comes to peak comfort, but let me tell you, there are so many heeled iterations that will let you walk pain-free. And as someone who has put a pair of boots on Vinted a week after buying them because of blisters, you can trust I won't make the same mistake again.

I haven't bought any new season boots, as yet, so I decided to have a look at some of my favourite Instagram accounts to get some inspiration for us all. What did I find? Emili Sindlev in this season's key animal print kitten heel boots, Emmanuelle Koffi in a classic style you'll love for years and Amaka Hamelihnck showing everyone how to make shorts and skirts last longer with the ultimate pair of knee-high boots. Here's 7 comfy boots outfits I'll be recreating on repeat this autumn.

COMFY BOOTS OUTFITS I'M ROTATING THIS WINTER;

1. Flat Tall Boots + Biker Jacket + Shorts

Best comfy boots

(Image credit: @amaka.hamelihnck)

Style Notes: A tall, flat boot has the power to make your summer skirts and shorts last throughout the cooler months. Make like Amaka and add a pair to a layered look comprised of a shirt, cardigan and leather jacket. When winter hits, just add tights and a wool coat.

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2. Kitten Heel Ankle Boots + Suede Jacket + Ecru Jeans

Best comfy boots

(Image credit: @femmeblk)

Style Notes: Light wash jeans needn't be reserved for the warmer months, instead, layer with autumn textures like suede. See how a jacket and comfy kitten heel boots makes the humble jeans feel fresh for new season? Perfection.

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3. Western Boots + White Dress + Wool Coat

Comfy boot outfits

(Image credit: @lucywilliams02)

Style Notes: Western boots are key once again this year, but instead of an in-your-face fussy pair, give a sleek nod to the trend with simple details such as a low angled heel and a square-toe. Lucy proves how these will work with any classic outfit.

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4. Riding Boots + Roll Neck Jumper + Mini Dress

Comfy boot outfits

(Image credit: @emmanuellek_)

Style Notes: Everyone from Mango to Toteme has created riding boots this season––wear them the Parisian way with a fine roll neck knit and layered mini dress duo.

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5. Chunky Chelsea Boots + T-shirt + Trench Coat

Comfy boot outfits

(Image credit: @smythsisters)

Style Notes: Simple, effortless and easy to copy––this T-shirt, trench coat and Chelsea boot formula is one that'll save the day on many "I have nothing to wear" mornings.

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6. Leopard Loose-Fit Tall Boots + Quilted Jacket + Sleek Bag

Comfy boot outfits

(Image credit: @emilisindlev)

Style Notes: Animal print boots (and everything in leopard, for that matter) is huge for autumn. Emili proves how lively knee-high boots can also be comfy by opting for a loose-fit, low-heel style. See, practical boots needn't be boring!

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7. Block Heel Boots + Skirt Co-ord

Comfy boots outfits

(Image credit: @vikilefevre)

Style Notes: Ticking off all the credentials for a great autumn/winter 2024 boot––suede, knee-high and a wearable heel height––Vikile styles hers with a co-ord. Basically the easiest outfit you can rely on for any season.

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Freelance Fashion Editor

Harriet Davey is a freelance fashion editor who has been part of Who What Wear's extended team since 2017. She previously worked in print at Look magazine and has since worked across print, digital and social for many other titles, including British Vogue, Stylist, Grazia, Refinery29 and Marie Claire. Also a stylist, Harriet has had the pleasure of producing cover shoots and editorials along with commercial shoots for brands including Boux Avenue, Watches of Switzerland, Benefit Cosmetics and Revolution. To add to this, Harriet also works in live TV styling for ITV’s This Morning. Back to Who What Wear. With hundreds of published stories on site, Harriet knows what the WWW reader wants. Keeping up to date with the latest It buys and runway trends, she can guarantee to keep you one step ahead of the most stylish people. When not writing or styling, Harriet loves to go shopping (yes, more fashion). If she’s not in a local Hackney bar or restaurant, you can find her forever searching for her next holiday destination.