Men's Dress Shoes: Guides and Top Picks

Dress Shoe Size vs Sneaker Size: How Much to Size Down

Most men wear a dress shoe a half to a full size smaller than their sneaker size. Conversion table, reasons, and brand notes.

How each construction is made, how to tell them apart, what a resole costs, and which one to buy.

Chukka vs desert boot vs Chelsea, the four main types, what to wear them with, and how they should fit.

Seven Chelsea boots from under $75 to $500+, with pros and cons, plus the most comfortable, budget, and office picks.

Snug, not tight. A thumb's width at the toe, firm at the ball, a quarter inch of heel slip at most. The 5-point check.

A Chelsea boot is a laceless ankle boot with elastic side panels. Types, toe shapes, history, fit, and outfits.

Nine lace-up, Chelsea, and chukka dress boots from under $75 to $500+, with the most comfortable picks and best brands.

Seven Derby shoes from under $75 to $500+, sorted by comfort, office wear, casual wear, summer wear, and build quality.

Eight single and double monk strap shoes from under $75 to $500+, compared by materials, construction, fit, and drawbacks.

Ten penny, tassel, and bit loafers from under $150 to $500+, with the most comfortable and best casual picks.

Ten Oxfords from under $75 to $500+, compared by construction, fit, and the one drawback of each.

Penny, tassel, horsebit, Belgian, and driving loafers compared, plus loafer vs slip-on, socks, and fit.

An Oxford is a lace-up shoe with closed lacing. The six types, Oxford vs Derby, formality, and fit.

Monk straps close with a buckle instead of laces. Single vs double, how formal they are, and how to wear them.

A Derby is a lace-up shoe with open lacing. The main types, Derby vs Oxford, socks, and outfits.

Dress boots vs dress shoes, the five types ranked by formality, and how to wear boots with a suit.