Shop Men's Leather Boots, Handmade and Goodyear Welted

Men's Boot Styles Compared

The closure decides how a boot fits and how dressy it looks. Here is how the main styles in this collection differ.

Chelsea and Jodhpur Boots

Both are slim, low profile ankle boots that sit neatly under a pant hem. The Chelsea pulls on with elastic gussets; the jodhpur closes with a strap around the ankle and reads slightly dressier.

Chukka and Lace Up Derby Boots

Lace up boots give the most adjustable fit over the instep. A chukka has two or three eyelets and a relaxed feel, while a derby boot adds more eyelets and a sturdier profile for colder months. Lace up boots are the easiest choice if you have a high instep or wear thicker socks in winter.

Zip, Monk Strap and Button Boots

A side zip gives a clean, laceless line, buckles add detail, and button boots revive a Victorian pattern for men who want something rarely seen.

Dress Boots or Casual Boots

• Dress boots: smooth calf, slim last, leather sole. Chelsea, jodhpur and zip boots in black or dark brown work with a suit.
• Smart casual: suede Chelsea boots, chukkas and wingtip boots with chinos and a jacket.
• Casual: derby and biker boots in grain leather or suede with denim and knitwear.
• Western: for cowboy styles, see our custom cowboy boots.

Leather, Suede, Patina or Exotic

• Calf: takes a shine and suits dress boots in black, brown and burgundy.
• Suede: soft and relaxed, in tobacco, navy and gray.
• Hand painted patina: layered color in shades you rarely find, including gray, olive green and blue boots for men. See our patina shoes.
• Norwegian stitch: hand stitched aprons on sturdier boots. Browse the Norwegian stitch collection.
• Exotic: crocodile grain, ostrich, stingray and python. Browse our exotic shoes.

Why Goodyear Welted Boots Last Longer

Boots take more strain than shoes, so construction matters more. Ours are Goodyear welted: the sole is stitched to a leather welt rather than glued, so a cobbler can resole them many times and the upper, which is the expensive part, keeps going for years. A cork layer under the insole also molds to your foot over the first few weeks, so a welted boot gets more comfortable the longer you wear it, which a glued boot never does.

How Men's Boots Should Fit

• Order your usual dress shoe length; most boots need no size change.
• Pull on boots should grip the heel firmly, with slight lift at first.
• Lace up boots should close comfortably over the instep.
• Choose width separately, from D to EEE.
• Check our shoe size guide before ordering.

FAQs

What boots should every man own?

Most men are well served by two pairs. A black or dark brown leather Chelsea boot covers suits, smart casual outfits and evenings, because its slim, laceless profile sits neatly under tailored pants. A brown suede chukka or derby boot handles weekends, travel and colder days with chinos and denim. From there, a patina or exotic boot adds personality, and a jodhpur or zip boot gives a dressier alternative to a Chelsea.

Can you wear boots with a suit?

Yes, as long as you choose a slim dress boot. A black or dark brown calf Chelsea, jodhpur or zip boot with a leather sole looks sharp with a suit and keeps your ankles covered when you sit. Make sure your pants are hemmed with little or no break so they fall cleanly over the boot. Chunky derby, biker or lug sole boots are too casual for tailoring and look better with denim.

What is the difference between Chelsea and chukka boots?

A Chelsea boot has no laces; it pulls on using elastic gussets on each side, which gives it a slim, clean silhouette that works with suits and smart casual clothes. A chukka boot has two or three pairs of eyelets and laces up, which makes it more relaxed and adjustable over the instep. Chelseas lean dressier, chukkas lean casual. Many men own one of each to cover both ends of the wardrobe.

Should men's boots be a size bigger?

Usually not. Order your normal dress shoe length, because a boot that is too long slips at the heel and creases in the wrong place. If you plan to wear thick socks or have a wide or high volume foot, choose a wider width rather than a longer size. Pull on boots such as Chelseas should feel snug at first, since leather relaxes slightly with wear, while lace up boots can be adjusted.

Are suede boots good for winter?

Suede can handle cold, dry winter days very well, and it looks warmer and softer than polished calf. It is less suited to heavy rain, slush and road salt. Treat suede boots with a protective spray before wearing, brush them after each wear, and let them dry naturally if they get wet. For regular wet winters, a grain leather or calf boot with a Goodyear welt is the more practical choice.

Can you wear Chelsea boots with jeans?

Yes, Chelsea boots are one of the best boots to wear with jeans. Choose slim or straight leg denim that ends just at the top of the boot, either hemmed or with a small cuff, so the jeans do not bunch over the ankle. Dark denim with black or dark brown calf Chelseas looks sharp enough for an evening out, while suede Chelseas in tobacco or gray feel more relaxed. Avoid very wide jeans, which hide the boot's clean shape.

What color boots are most versatile for men?

Dark brown is the most versatile boot color. It works with navy, gray, olive and tan pants, with every wash of denim and with most suits outside black tie. Black is the next choice, dressier and ideal with charcoal and black clothing. After those two, burgundy adds warmth without being loud, and tan or tobacco suede suits casual outfits. Patina colors such as gray, olive green or blue are best as a third or fourth pair.

How long do Goodyear welted boots last?

With rotation and care, Goodyear welted boots can last ten years or more, often much longer. Because the sole is stitched to a leather welt instead of glued, a cobbler can remove a worn sole and stitch on a new one while the upper stays intact. Use cedar boot trees after wear, rest pairs a day between wears and condition the leather every few weeks, and a good pair will outlast several soles.

Looking for shoes to wear alongside your boots? Explore our full range of handmade men's shoes.