When most men think of buying dress shoes, their first instinct is usually to spend as much or as little as they can on some shiny, super-slim black shoes. While this is a great strategy if you make a living as a maître d’ or a funeral director, there are many more flavorful ways to rock shoes suitable for evening events. A man should only wear one sort of shoe to a wedding (lace-up oxford), but for all other formal occasions (dinners, business dinners, dates, business dates) you can dress things up a bit while still retaining some thoughtful edge.
Get the right pair up front and with enough time, you will soon be reaching for all these handsome devils in the afternoon too, just to walk with some extra swagger.
Brogues, those shoes with the holes in them, are traditionally thought of as "country shoes." After all, the reason they had the holes originally was to help water from dank bogs drain out while you were hunting. However, it is now totally acceptable and in many cases encouraged to wear them in the city.
Don't be afraid to spend as much money as you can afford on a sturdy, substantial pair. They can be rocked with everything from oxford shirts and cardigans to tweed blazers and polos. And they always, always go with nicely fitting dark blue jeans. Perfect for date night. If you show up wearing natty brogues, you are at the head of the race, my friend.
Elliot’s choice: these chocolate brown suede joints from the don dada of funky country shoes, Mark McNairy. They are extra special but not overly flashy. The white eyelets say it all.
The loafer's chief competitor in the evening casual space is usually the sneaker. While sneaks are fine for the weekend (afternoon), you should be stepping things up a bit come nighttime with a handsome brown loafer. Unlike brogues and cap toes, where I encourage you to go big and drop some cheddar, you can find a perfect loafer for around $150 from any number of mainstream brands.
I'm a traditionalist in this department, so my advice is to go with something that looks a few steps up from what you imagine Dustin Hoffman would have worn in The Graduate. Something collegiate and smart-ass, not dad-like. No thick soles, no stitching on the sides.
Elliot’s choice: classic Bass model. You won't stick out too much when you wear it, but it will be clear you have your shit together in an easy, comfortable way. Oh look, it's even on sale right now.
I am at an age where despite being a raging bohemian I receive no fewer than 10 wedding-related shoe emails per week. Now, assuming that the wedding is not black-tie, you can totally wear brown shoes to a wedding. If someone wants to revoke my card now, we can have words outside. Besides, compared to the undertaker trainwrecks other dudes will be showing up in, if you wear something sleek, sharp and well balanced you will be a minor king.
The natural mates for shoes like these are suits in the gray and blue family. Because the silhouette of the shoe is slimmer, you will want to wear these with light wools rather than heavy tweeds (which would go great with your brogues, btw). If you are that sort of guy, you can also wear these with lighter, nicely fitted jeans and an immaculately clean white shirt with a semi-spread collar for a look that is very uptown to the point of being sorta edgy.
Elliot’s choice: This gorgeous collaboration between Spanish brand Carmina and NYC shop Epaulet is fresh on the racks and kicks with life.