Autumn Winter Footwear Buying Guide 2025

As the nights draw in and the temperatures drop, it’s natural to face pivoting priorities when it comes to fashion. No longer can we simply wear whatever we like – now we must first think about practicalities.

Getting the decision right, though, is key to enjoying whatever you get up to in this autumn/winter season. The key concerns of cold weather, plus rain, hail or even snow, mean your feet need to be as snug as possible all day long. Add that to the prospect of icy terrain to navigate and footwear becomes one of the most important parts of your outfit.

Finding it difficult to pick out a great pair of shoes that looks amazing and will keep your toes toasty? Don’t worry. We’ve got the perfect recommendations for every occasion this autumn and winter.

Everyday comfort

Possibly the most important pair of shoes in your collection this winter will be your go-to everyday favourites. These are the shoes that complement any outfit, that keep your feet warm and dry and that, crucially, feel comfortable to wear all day long.

Think they’re a myth? Think again.

The key aspects you need to look for in this kind of shoe are:

• Ease of fastening - for when you're in a hurry.
• Stylish design - so looking put-together is effortless
• Showerproof materials - to keep the rain and snow at bay
• Ridged sole - for traction in slippery conditions
• Comfortable insole - to keep your feet happy

Editor's picks

Ladies

Dr Lightfoot Slip On Quilted Top EE Fit Shoe – Black

Also available in Navy.

FROM £25

SHOP THIS STYLE

Men's

Mens Leather Touch Fasten Shoe – Black

Also available in Brown.

FROM £39

SHOP THIS STYLE

Classic casual

Next up, how about something simple and effective for those days when you don’t want to wear the same old favourites? Enter the go-to weekend shoe – ideal for casual get-togethers and gatherings as well as running errands.

For this shoe, you’ll want to keep an eye out for the same vital features you need in your everyday shoe, but in something that looks a little different. Think ankle boots or sporty trainers! The key here is to match the practical aspects of the footwear while giving yourself a touch of variety in design.

Editor's picks

Ladies

Leather Zip Boot with Thermal Lining – Black

Also available in brown and tan.

FROM £55

SHOP THIS STYLE

Men's

Pegasus Leather Wide Fit Lace Trainer – Black

Also available in brown, navy and tan.

FROM £32

SHOP THIS STYLE

Snazzy styles

The autumn winter season isn’t complete without Christmas parties, festive get-togethers and even the odd wedding or two – so you’ll need a pair of shoes that look the part without leaving you cold and uncomfortable all night.

For men, most leather styles offer equivalent protection against the weather, so the deciding factor will likely be style. For the most impact compared to your other footwear, opt for a formal style that’s a cut above the rest.

For the ladies, it can be more difficult to find a shoe that’s suitably stylish without compromising on comfort in what could turn out to be chilly temperatures. With that in mind, we advise pairing your footwear with snug garments like fleece-lined tights to stay warm and stylish.

Editor's picks

Ladies

Sling Back Sandal – Pewter

Also available in black, navy and white.

FROM £26

SHOP THIS STYLE

Men's

Pegasus Wide Fit Leather Brogue – Black

Also available in tan.

FROM £42

SHOP THIS STYLE

Snug slippers

Last but not least, the one thing we all need on a cold winter night is a pair of slippers to keep the chills at bay. Your slippers should of course be as cosy as possible, but don’t forget to think about functionality and style as well.

For many, slippers represent their everyday indoor shoe, meaning you might wear them more than any other item of footwear. That’s why it’s so important to choose a design that is comfortable and safe for walking in, helping you to avoid slips and trips inside the home.

Whether you wear slippers all the time at home or just when you’re gathered in for the night, it’s likely that not many people will see them apart from your loved ones at home – and the postie, of course! So this is the perfect opportunity to pick a bold colour or style that shows off your personality, without having to worry about how many outfits it matches.

Ladies

Padders Camilla Extra Wide EE Fit Slipper – Red

Also available in blue, grey, lavender and navy.

FROM £39

SHOP THIS STYLE

Men's

Faux Suede Fleece Lined Slipper – Tan

Also available in Black.

FROM £20

SHOP THIS STYLE

Autumn Winter Footwear at Chums

Whatever your plans are this autumn and winter season, we’ve got you covered with the best footwear styles for men and women. Find your next favourite pair today.

SHOP FOOTWEAR