Get your own personal stylist to help you find clothes you love. All online, completely free

Sign In

What goes with what

The Thread Guide to: Boots

The Thread Guide to: Boots

The days might soon be getting shorter – and the sun showing its face a tad less frequently – but the good news is that boot weather is upon us. In fact, boots are as useful in early autumn as they are in winter, says Thread stylist Alice Watt.

Why boots are the best thing to wear in early autumn

"Boots are a nice transition piece as the weather slowly becomes more autumnal," Alice explains. "You can stick to your usual t-shirt and shirts, but wear boots to keep you warmer, save your feet from getting cold or wet as the temperature dips, and stop you from looking unseasonal when your clothes seem summery but it's still starting to get chilly."

The best beginner boots

If you're wary of wearing boots because they seem like too much of a statement, start with desert boots. "They're the perfect beginner boot," Alice says. "They give an outfit structure like boots, but they're as comfortable and easy to wear as trainers. Throw them on with jeans or chinos all autumn."

Why boots are worth investing in

"Boots are usually a bit more expensive than regular shoes, but they're worth spending on for three reasons," Alice says. "One, they're timeless. The five boot styles below have been around for forever, and they'll never go out of style. Two, you can wear them for years because they work on guys of every age, and three, they age well. Boots are sturdier and more durable than regular shoes."

Here, Alice shares the basics you need to know about our five favourite types of boots. A bonus: they’re arranged from most casual to smartest.

Desert boots

Boots to consider: Clarks brown leather desert boots (£99), Clarks brown suede desert boots (£95), Joules grey suede desert boots (£75)

Why we like them: Desert boots are the perfect autumn and spring boots. They’re lightweight, they go well with jeans and chinos, and because they don't cover the ankle, they're really easy to wear.

Comfort level: 9/10. They're light and mould to your feet.

Clothes they go with: Anything casual and utilitarian. Think jeans, t-shirts, jumpers, Harrington jackets and field jackets.

Clothes they don't go with: Any shirt that's smarter than an Oxford shirt. Desert boots should stay casual.

Seasons they work in: Autumn, spring, summer.

Care tip: Suede protectant spray might seem like a faff, but it can double the lifespan of a pair of desert boots. Here's why: suede picks up dirt more than regular leather, and the rough texture can look knackered more quickly. But a spray makes the suede much more resilient. 

Trouser tip: Desert boots end lower on your ankle than most other boots, which makes them work with basically any trousers. Wide-leg trousers, however, aren't quite right: they swamp desert boots' slim shape. 

Work boots

Boots to consider: Red Wing brown work boots, photographed (£249); Red Wing brown work boots (£229); Fracap brown work boots (£160); Dr. Martens red boots (£100) 

Why we like them: Work boots are the most masculine, durable and long-lasting boots. And because they're military-inspired, they're easy to wear well with utilitarian basics like jeans and knit jumpers.

Comfort level: 7/10. They might take a while to break in.

Clothes they go with: Anything military-inspired and masculine, particularly indigo jeans, field jackets, knit jumpers, utility shirts, military jackets and flannel shirts.

Clothes they don't go with: Anything too smart (such as formal trousers or shirts) or too lightweight (light chinos). Work boots are hard-wearing and substantial, so they should be worn with similar clothes. 

Seasons they work in: Autumn, winter, early spring.

Care tip: The boots themselves are low-maintenance: just wipe with a cloth if they look dirty. As you break a new pair of workboots in, a soft, thick pair of socks will save your feet from break-in blisters. 

Trouser tip: Thick, raw jeans (like selvedge denim) look great with work boots because they're both quite rugged. And because work boots end higher on your ankle, you can show them off with a two-inch turn-up at the bottom of your jeans. 

Lace-up leather boots

Boots to consider: Burberry black lace-up leather boots (£575); Hudson black lace-up leather boots, photographed (£125); Base black lace-up leather boots (£80) 

Why we like them: Think of lace-up leather boots as work boots’ more refined cousin. They have the same masculine aesthetic – but because lace-up leather boots are lighter and less clunky than work boots, they go well with smart-casual clothes like chinos and shirts. 

Comfort level: 8/10. They're a bit softer than workboots, but they can still take a week or two to break in. 

Clothes they go with: Smart-casual staples like grey and black chinos, indigo jeans, jumpers and Oxford shirts. They also work well with smart outerwear – for instance, quilted jackets.

Clothes they don't go with: These boots might be smarter than work boots, but they’re still not sharp enough to wear with blazers or suits.

Seasons they work in: Autumn, winter, early spring. 

Care tip: Lace-up leather boots look great for ages with little maintenance. Just wipe them clean whenever they need it, and give them a polish if they start to look tired. 

Trouser tip: These boots' slim shape makes them look good with slim or straight-leg chinos or jeans. If your trousers are so long that they bunch around the tops of the boots, turn up the bottoms by an inch or two to make your legs look leaner.  

Brogue boots

Boots to consider: Church's black brogue boots (£355), Grenson black brogue boots (£230), Base black brogue boots (£100), Topman black brogue boots (£55)

Why we like them: Brogue boots, particularly black brogue boots, go with almost everything. And because they fall halfway between super-sharp Chelsea boots and rugged work boots in the smart-to-casual spectrum, they're the ideal boots for smart-casual occasions. 

Comfort: 7/10. The thick leather lasts, but also takes some getting used to.

Clothes they go with: A wide range of clothes. They look good with slim, dark denim jeans and light jumpers, but you can also wear them with formal trousers and a jacket.

Clothes they don't go with: Black brogue boots are too dark to wear with stone or coloured chinos. And because they're quite sophisticated, they don't look right with very casual clothes: hoodies, graphic t-shirts or any bright colours or prints.

Seasons they work in: Autumn, winter, early spring. 

Care tip: Since they're meant to smarten up your outfit, you should keep brogue boots polished. And while they can be tough to break in, these boots also last forever. Save your feet in the first week or two by wearing thick socks. 

Trouser tip: Brogue boots look best with tapered or slim trousers that cover only the first one or two lace holes.

Chelsea boots

Boots to consider: Grenson Chelsea boots, photographed (£220); Base Chelsea brogue boots (£80); Selected black suede Chelsea boots (£90)

Why we like them: Chelsea boots are the most formal boots. They're iconic, they work with everything from suits to slim jeans, and they make already-smart outfits look a bit more considered. 

Comfort: 8/10. Because Chelsea boots have elasticated ankles, they're easy to slip on as you run out of the house—and you don't run the risk of over-tight (or loose) laces.

Clothes they go with: Everything smart, from suits down to slim jeans and fine-knit jumpers. Younger guys (à la Harry Styles) are increasingly wearing them with skinny jeans, too.

Clothes they don't go with: Because of their narrow shape, Chelsea boots don't work well with wide or relaxed-fit jeans, shirts or jumpers.

Seasons they work in: Autumn, winter, spring.

Care tip: Because of their reputation for smartness, you should keep Chelsea boots in tip-top shape. Polish them regularly and take them to the shoemaker the minute the soles or heels look too worn. At around £20, it will be much cheaper than buying a new pair when you get an inevitable hole in the heel.

Trouser tip: Proportionally, it makes sense that you should wear Chelsea boots with trousers that are slim and smart. Don't worry about the length; it's no big deal if you can't see the whole boot (although your trousers shouldn't be so short that you can see your socks when you're standing).