We’ve Found the Best Affordable Boots to Wear With All Your Dresses This Autumn

Boots, glorious boots. What would we do without them? Nothing beats that fresh-out-of-the-box, new-boot feeling (apart from perhaps the elation when you find a pair that doesn’t give you blisters on the first wear). As a staple of our wardrobes pretty much year round, boots of all kinds really do deserve a medal for how many footwear dilemmas they see us through and especially for how versatile they make our wardrobes. 

The perfect western pair will tone down a dressy dress and make those summery styles feel suddenly autumn/winter appropriate. A polished ankle boot will elevate jeans and a T-shirt. Anything with a heel suddenly makes wide-leg trousers actually wearable and a knee-high does wonders for a midi or mini dress.

The beauty is that fashion trends come and go, but buy a classic boot and they will last you for years. I promise I’m not just saying that—the black ankle boots I currently have on from Arket are heading into their third winter and still going strong despite the fact that I wear them on repeat. This also proves you don’t have to spend thousands to ensure they last. Just make friends with your local shoe-repair shop and pop in for a polish or re-sole every once in a while and they’ll feel good as new.

There is a lot of choice out there, though, and if you’re anything like me and struggle to make a decision on what to have for lunch, you might be slightly overwhelmed if you’re currently searching for a new pair. So, below I’ve pulled together 25 of the best boots on the market right now for under £250. I’ve also made I’ve made sure they work with all your autumn/winter dresses (or skirts) as well as your favourite jeans— to maximise the wear you’ll get out of them. Keep scrolling to see (and shop the styles you fall for).

These elevated riding-style boots look SO expensive. 

This is the style I’ve owned for years and they’re still my favourite. 

I’ve had my eye on these uber-cool boots for a good few weeks now and I think they may be my boot purchase of the year. 

These timeless boots have a hint of seventies chic to them, meaning they’ll work perfectly with all those floaty floral dresses you own. 

Another high street pair that wouldn’t look out of place on a catwalk. These are just so elegant. 

If you haven’t invested in a pair of long, flat chunky boots yet— what are you waiting for? These will take you all through spring with shorts and mini dresses and then into winter too. 

The best dupe I’ve found for those celebrity-loved boots. 

I’m a sucker for a western boot, and there’s no denying these are really fun for wearing under skirts and dresses. 

These could just as easily be out-out boots as day boots. 

The rounded toe and deep burgundy colour instantly make these boots look designer. 

Bring your chunky boot addiction into spring. 

Minimalist but still incredibly cool. They’ll look great with pleats. 

A nod to the cowboy trend that still feels really polished. 

Such a gorgeous chocolate brown. 

A block heel will mean you stay comfortable all day as well. 

I’d wear these under wide leg jeans for a more grown up look. 

Basic but not boring. 

This is a surprisingly versatile colour that will work in autumn, winter and spring.

Of course, Ralph Lauren does the most timeless riding-style boots. 

White can feel really fresh in autumn/winter too. 

Wear these with midi skirts and tights. 

A modern classic. 

The pointed toe makes a basic black boot feel really refined. 

The block heel means these will be so comfy. 

Dr.Martens have proven they’ll never get old. 

Next Up: 6 Items Every London Girl Has in Her Autumn Wardrobe