Quick answer: Leave about a thumb's width in front of your longest toe, expect a snug but not painful fit across the widest part of the foot, and only slight heel lift when walking.
Length and width
There should be room to wiggle your toes. The ball of your foot should sit at the widest part of the shoe.
Style changes fit
Oxfords are slimmer over the instep; derbies like our lug sole brogues open wider; loafers should be snug.
Break-in
Leather softens over a few weeks. Pain on day one usually means the wrong size.
Frequently asked questions
Should I size down for loafers?
Usually not — order your normal size; they should feel snug at first.
What if I am between sizes?
Choose the larger size for lace-ups.
Shop the store: oxfords · loafers · derby & brogues. Free U.S. shipping on orders $150+, 30-day returns on unworn shoes.