The checklist
- Construction: welted boots can be resoled and handle wet weather better than cemented ones.
- Sole: a rubber commando or Dainite sole handles rain and winter; leather soles are for dry days.
- Suede or leather: suede is warmer looking and surprisingly hardy when sprayed; calf leather is dressier.
Set your budget
The men’s luxury boots we researched sell for $350 to $3,300 in the US. Decide how often you will wear it first; the most expensive piece is often a skip for everyday life.
Buyer tip
Boots see big end-of-season markdowns in January; buy welted classics from British makers when the pound is weak against the dollar or euro.
Buying in Europe
Buying in Europe: Italian and French sizes are used on most designer shoes, and they differ from US sizes by brand. Check the house’s own size chart, and remember that many Italian brands run about half a size small.
Ready to buy?
Jump to our buy-or-skip list of men’s luxury boots.
Recommended products

Buy this firstJohn Lobb · Men’s luxury boots
John Lobb Lawry Boot
Chelsea from John Lobb.
- Verdict
- Buy
- Best for
- Peak Chelsea
- Typical price
- $2,100–$2,400
Pros
- Superb
Cons
- Expensive

ChelseaJohn Lobb · Men’s luxury boots
John Lobb Romsey
Romsey.
- Verdict
- Buy
- Best for
- Chelsea
- Typical price
- $2,300–$2,600
Pros
- Superb
Cons
- Pricey

Chelsea iconR.M. Williams · Men’s luxury boots
R.M. Williams Craftsman Boot
One-piece leather Chelsea, resoleable.
- Verdict
- Buy
- Best for
- Chelsea icon
- Typical price
- $650–$750
Pros
- Durable
- Resoleable
Cons
- Runs wide
Frequently asked questions
What should I check before buying men’s luxury boots?
Construction: welted boots can be resoled and handle wet weather better than cemented ones. Sole: a rubber commando or Dainite sole handles rain and winter; leather soles are for dry days.
What are the most versatile men’s boots?
A dark brown suede or black leather Chelsea boot works with jeans, chinos and casual suits.
Are R.M. Williams boots worth it?
Yes, for a Chelsea boot built from a single piece of leather that can be resoled. Check the fit; they run wide.