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Style Advice

Four essential autumn shoes

Four essential autumn shoes

As the weather starts to turn, it’s your cue to look away from the sun and down at your footwear – an outfit choice that can make or break a mood if it’s not durable enough to face the elements. You don’t, after all, want to get caught short in a downpour in your boxfresh trainers, but on warmer days, chunky boots can feel like overkill. 

“The transition from summer to autumn is a great time to make small tweaks to what you would usually wear,” says Thread stylist Alexander McCalla, “so try switching to higher top shoes, which are great for dealing with changeable weather conditions. Smart casual lace-up boots are easier to keep presentable in wet weather, and colourful footwear keeps your outfit fresh and exciting, even when the weather isn’t.” To prepare you for all autumn forecasts, we've rounded up the four shoes that will guide you through the season in style, whilst keeping your toes comfortable and dry – only tiny puddle jumps required. 

Photographed: Similar AllSaints Jarred Shoe (£99)

Bolder black Derbys 

Black Derbys with a chunky sole give a bolder finish to a formal outfit. That little extra lift brings a stylish touch to your work wardrobe in the colder months, and the thicker sole will better prepare you for wet weather. 

Look for: “A rounded toe tends to be more versatile than almond shapes, and can be easily paired with any smart trousers,” Alexander says. “Summer is about sleeker styling, so as the seasons turn these shoes are a great way to add some weight to your work aesthetic.” How chunky you choose to go is a matter of preference. Pick a commando sole if you’re a bold dresser, or a rubber grip sole if you want a practical seasonal look that’s not so military-looking when paired with formalwear. 

How to wear them: With your usual work attire. Derbys, chunky or otherwise, will always be a formal footwear classic. Whether you’re wearing a cotton suit, flannel trousers, or a print like houndstooth or pinstripes, a pair of black lace ups are the perfect finish.

Where to wear them: Work, weddings, special events, or any formal occasion that calls for Derbys – but don't overlook them for smart casual settings too. The chunky sole relaxes a typically smart style, so they won’t look out of place teamed with wide fit trousers or jeans.

Versatile leather chukka boots 

Leather chukkas are easy to keep fresh in autumn’s elements and are more durable and weather resistant than suede desert boots. They’re ideal for adding a smarter finish to casual outfits and will run you into winter seamlessly.

Look for: Crepe soles offer good grip and are a nice alternative to combat sole boots, as they still look smart but are suitable for casual wear. 

How to wear them: Whilst chukka boots can dress down tailored-fit trousers, a crepe-soled style also pairs effortlessly with rolled-up denim or cargo trousers. “It all comes down to how your trousers sit on the shoe, so steer clear of skinny jeans, which proportionally won’t flatter," Alexander says.

Where to wear them: Whether you need some durable footwear for walking, or are looking for some smart yet stylish boots to finish off a casual autumn outfit, chukkas are an obvious go-to.

Photographed: Grenson Joseph (£285), Barena Drawstring check trouser (£137)

Classic lace-up boots 

A durable boot is the perfect choice for autumn, as they cover more of your foot in wet weather and can be easily dressed up or down for work or weekend wear. 

Look for: Dark brown woody tones are great for the season,” Alexander says, “but if your wardrobe is mainly navy and black, go for a darker colour. A bit of grip is better in wet weather so chunky commando soles are ideal.” When picking fabrics and features, consider if you want something distinctive like pebble grain, sleek and smart like high shine, or more casual like a cap toe. 

How to wear them: In office settings, they look smart with tailored trousers, especially in tweed or neutral tones. For smart casual outfits, try rolled-up denim or chinos. Wearing combat boots shouldn’t feel like you’re going to battle – they should be easy to throw on with anything. 

Where to wear them: The beauty of lace-up boots is that they’re never out of style and appropriate for most occasions, so whether you’re at work, on a date, or just out and about over the weekend, you know you’ve made the right choice.


Statement-making trainers 

Whether you’re going for monochrome, multi colours, or interesting takes on classic shapes, bold trainers brighten up the muted tones that typically form our autumnal outfits. A statement shoe is an effortless finish for any casual look. 

Look for: A pair that will be the hero of your outfit. The punchier they are, the more neutral the rest of your look should be, but have fun and don’t worry too much about the styling.

How to wear them: When you don't want to have to overthink getting dressed, bold trainers are an easy way to add life to your outfit. Style with a simple sweatshirt and jeans to balance out the brightness and avoid a clown vibe.

Where to wear them: Bold trainers are perfect weekend wear, especially when you’re not sure how to make a casual look pop. Rock these at the pub, the park, on a dinner date, or a day out with friends. As a bonus, they’re a welcome distraction from doom-and-gloom skies.

Words: Ella White
Photography: Jake Millers
Styling: Alexander McCalla