Finding the perfect dress shoe is a feeling like few others — it makes you feel like a successful grown-up. Sadly, it’s one that way too few guys get to experience. The reality is that the majority of men don’t know squat about dress shoes and settle for ugly, uncomfortable shoes when they could just as easily be rocking wicked kicks.
No one expects you to become a connoisseur of balmorals and brogues and wingtips — and certainly no one expects you to fill a closet with all kinds of shoes you’ll wear only once or twice in your life — but every guy should own two good pairs of dress shoes. That’s all you need.
And I’m about to make it extra easy on you by telling you exactly what shoes to buy.
Shoe #1: Black oxfords
First, get yourself a quality pair of black oxfords. If you own just one pair of dress shoes, it should be black oxfords (also called balmorals). They should look something like this:
Look for a cap-toed shoe with no broguing (more on what that is later — for now, just worry about whether your shoe looks like the picture above). Avoid thick rubber soles, though rubber is okay if you can’t afford a leather sole. At all costs, avoid slip-ons, shoes with square toes and shoes with excessively pointy toes. Shoes like these are still common, but they are horribly out of style (and were never really in style in the first place). No square toes!
For my money, the best black oxfords on the market are Allen Edmonds Park Avenues. They’re pretty pricey, though — coming in at over $300. If that’s out of your range, Johnson & Murphy makes a cheaper alternative that still looks decent.
Black oxfords are formal shoes, so you should only wear them when you’re wearing a suit — unless you’re pretty good at this fashion stuff. When you’re not wearing them, store them in a cool, dry place (inside a box in your closet is fine).
If you keep your oxfords in good shape by cleaning and polishing them regularly, they’ll last you for years.
Shoe #2: Brown brogues
Your second pair of dress shoes should be should be appropriate to wear with a suit, too, but they should be a bit more casual. Not football-game-with-your-friends casual — you can wear sneakers or whatever the heck you want for that. We’re talking dinner-date-in jeans-and-a-blazer casual or at-the-office-in-chinos-and-a-button-down casual.
Pick up a pair of brown brogues, perhaps the most versatile shoes in the world. They should look roughly like this:
See those little decorative circles? That’s called broguing. It looks fancy, but shoes with it are actually less formal than shoes without it. When the broguing on the toe cap of the shoe comes to a point in the middle, the shoes are called wingtips.
Again, Allen Edmonds is killing it when it comes to these shoes. The company’s Strands are legendary among the #menswear crowd and McAllisters are a great option if you prefer wingtips. If you have the cash, you won’t regret dropping a little over $300 on them. There are several cheaper options that are really good, too. Stafford Ashtons are a great alternative — and they can be had for less than $100 at JCPenny. The Giorgio Brutini Medallion is another good choice for those on a budget.
Wearing your new shoes
Okay, so you now own two pairs of dress shoes. When should you wear them? What should you wear them with?
The most obvious scenario for wearing dress shoes is when you’re wearing a suit. Both the shoes above can be worn with most suits, but you’ll want to avoid pairing your brown shoes with anything too dark. Just keep this handy guide in mind:
Remember that your black shoes are more formal. Summer wedding outdoors? Brown shoes are great. Funeral? Maybe stick with black.
The other great thing about your brown shoes is you can wear them with clothing other than suits. Here are some looks for you to consider: