With winter approaching, it’s time to swap out the open-toe sandals and sling backs in favour of some winter boots and shoes with a little more weatherproofing. But winter shoes and boots don’t have to be boring. Party season is just over the horizon, so we’ve picked out a few of our favourite options that will be perfect for parties, or delightful for dog walking, but perhaps not for both.
Windsor Women’s waterproof mid-calf boots from Chatham Footwear
£210
There are plenty of stylish women’s winter boots around, but finding a pair that is as at home in muddy wood as with a thick winter maxi dress is much more challenging. For me, Windsor fits both briefs nicely.
These mid-calf boots, made of tan-coloured premium leather, have a thick rubber sole to keep feet well insulated and dry. The waterproof Sympatex lining adds another layer of protection from the elements.


The Sole Spring Poron cushioning is soft yet supportive, ensuring all-day wear without tiring the feet, while the breathability of the materials keeps them feeling fresh.
Style details like the raised seams and side buckle elevate Windsor from run-of-the-mill waterproof boots to everyday essentials with style and character.
Waverly Ankle Boots from Hush Puppies
£95
Adding a little Western wear into the mix is never a bad thing, in our opinion, and the Hush Puppies Waverly Ankle boot gives a stylish nod to this without going full-on Cowgirl.
Available in both tan and black, the leather features an elegant yet simple studded western wear design across the toes, with a studded line that follows the arch to the front edge of the boot.

A small 50mm block heel adds shape to the boot, and the flexible sole and memory foam leather insole make it comfortable to wear. The zip side makes it easier to get your foot in and out without much undignified pushing and pulling, which is a positive thing.
Waverly ankle boots work well with jeans and trousers or dresses and skirts, making them easy to dress up or down, depending on the occasion. They’ll come into their own next year, too, pairing well with denim shorts ready for festival season. A worthy investment for multi-season wear.
Lara flats from Toms
£42
Autumn and winter are the perfect times to add some colour and texture to your shoe collection. With the festive party season just around the corner, these velvet classic loafers in dark burgundy are a must.


The beautifully cut page boy styling creates a flattering shape that works well with jeans, trousers or dresses, making them highly versatile loafers. Inside, the CloudBounce insoles provide cushioned support, ensuring you won’t suffer from uncomfortable sore spots after a full day of wear.
The only downside is that the velvet outer might not be ideal for winter walks, but they will be a hit for party season.

