There was a time when dress shoes were for times when you, wait for it, dressed up. They were the shoes you put on when you had to wear a suit and tie and that was about it. As menswear evolves, those rules are changing. A dress shoe doesn’t just have to be a wing tip (although that’s still a classic style) and it can look as great with jeans as it does with a suit.
We rounded up 7 dress shoes that every guy should have in rotation in his closet. Regardless of the occasion, one of these shoes will fit the bill.
1. Black Cap Toe Oxford: Crockett & Jones Audley
The black cap toe oxford will work just about anywhere you need to wear a tie. Crockett & Jones makes theirs with calfskin leather that polishes up to a mirror shine and bark-tanned leather soles.
2. Brown Wing Tip: Florsheim Vincent
These work well with a suit, but also look great with a pair of raw denim jeans. As you wear them more a complex patina develops in the leather, giving them a color that is uniquely yours.
3. Chelsea Boot: Grenson Declan
Popularized by hip Londoners in the 1950s and adopted by The Beatles and Rolling Stones, the Chelsea boot has endured because of its dress up/dress down versatility and the comfort of the elastic side panels.
4. Penny Loafer: Bass Weejun
A preppy staple worn by everyone from JFK Jr. to James Dean, the penny loafer pairs great with a suit, but you can also rock them without socks for a more casual look. They’re also a great place to stash your change.
5. Chukka Boot: Clarks Desert Boot
Inspired by the boots British officers wore in World War II, not much has changed to Clarks classic desert boot, with its incredibly comfortable crepe soles, in 60-plus years. If it ain’t broke, don’t fix it.
6. Double Monk Strap: Alfred Sargent for J. Crew
Alfred Sargent has been making shoes in England for more than 100 years. These double monk straps take eight weeks to make, but they could quite possibly live longer than you will.
7. Comfort: Cole Haan Zerogrand No Stitch
Dress shoes don’t have to be heavy and stiff affairs. Cole Haan’s Zerogrand technology combines the comfort and lightweight nature of a sneaker with the refined styling of a dress shoe. Available in a bunch of fun colors, these will definitely turn heads.