Boots are the most useful footwear a man can own from October to April. They handle rain, cold and rough streets better than shoes, they add a bit of height and presence, and there's a boot for every style, from sleek chelsea boots under a suit to rugged work boots with raw denim. Here's every major boot style explained.
Chelsea boots
An ankle boot with elastic side panels and no laces. Created in Victorian England and made famous by 1960s rock stars, the chelsea boot is the most versatile boot there is.
- Sleek leather (black or dark brown): works with suits, tailored trousers and slim jeans.
- Suede (tan, brown, grey): smart casual, jeans and chinos.
- Chunky sole: more casual, pairs with workwear and streetwear.
Chukka and desert boots
An ankle boot with two or three eyelets and open lacing. The desert boot is a specific type of chukka with a crepe rubber sole, famously worn by British officers in North Africa during WWII.
- Wear with: chinos, jeans, corduroys, flannel trousers and smart casual outfits.
- Best materials: suede in sand, tan, brown or navy.
Brogue boots and country boots
A lace-up ankle boot with brogue perforations and usually a thick, grippy rubber sole. Heavier and more rugged than dress shoes, and perfect for British country style, tweed and cords, but also smart enough for a flannel suit in winter.
Service boots
A clean, lace-up leather work boot, originally a military design (the US Army's service boot). It's less bulky than a work boot and dressier, making it one of the best all-rounders for jeans, chinos and casual outfits.
Moc-toe work boots
The classic American work boot: a moccasin-stitched toe, a thick white wedge sole (originally for comfort on hard floors) and oiled leather in tan or brown. Iconic in American workwear. Wear it with raw denim, canvas trousers, flannel and chore coats.
Combat and military boots
Taller lace-up boots with heavy lug soles. Black or brown. Great with military-inspired outfits, black jeans and streetwear. Choose sleek, minimalist versions for everyday wear, and avoid overly bulky tactical models.
Engineer and harness boots
Pull-on boots with a buckle strap at the ankle and top, originally for railroad engineers and later motorcycle riders. Very rugged, and best with heavyweight denim and leather jackets.
Quick pairing chart
| Boot | Formality | Best outfits |
|---|---|---|
| Black leather chelsea | High | Suits, dark trousers, evening smart casual |
| Suede chelsea | Medium | Smart casual, jeans, chinos |
| Suede chukka / desert boot | Medium–low | Chinos, jeans, cords, knitwear |
| Brogue boot | Medium | Tweed, flannel, country style |
| Service boot | Medium–low | Jeans, chinos, casual layers |
| Moc-toe work boot | Low | Raw denim, workwear, flannel |
| Combat boot | Low | Military style, black jeans, streetwear |
How to wear boots with trousers
- With slim trousers or jeans: let the hem sit on the boot with a slight break, or cuff (turn up) jeans once or twice to show the boot.
- With wider trousers: let the trousers fall over the boot. A chunky sole balances a wider leg.
- With suits: use only sleek boots (chelsea or a slim dress boot), with the trouser hem covering the top of the boot.
- Socks: wool socks for warmth. With cuffed jeans, a visible grey or coloured sock adds character. More in our sock guide.
Boot care
- Brush off dirt after every wear.
- Use cedar boot trees to keep the shape and absorb moisture.
- Condition leather every few months; wax or cream polish for smooth leather.
- Spray suede with a protector and clean it with a suede brush and eraser.
- Remove road salt quickly with a damp cloth and a little diluted white vinegar.
- Resole Goodyear-welted boots when the sole wears thin. Good boots can last decades.
Choose dark brown suede or leather chelsea boots. They work with suits, jeans and everything in between, and they cope with most weather.
Frequently Asked Questions
Can you wear boots with a suit?
Yes. Sleek leather chelsea boots or slim dress boots in black or dark brown work well with suits, especially in autumn and winter.
What is the difference between chukka and desert boots?
A desert boot is a type of chukka boot with a crepe rubber sole, usually in suede. All desert boots are chukkas, but not all chukkas are desert boots.
What is the most versatile men's boot?
A dark brown chelsea boot, in leather or suede, works with the widest range of outfits from suits to jeans.
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