A gentleman's guide to picking the perfect dress shoes

John Lobb Marldon Dress Shoes.

Dress shoes are like the grown-up version of your favorite sneakers—formal, polished, and designed for those times when you need to look like you know what you’re doing. They’re usually made from leather, and whether it’s a wedding, a big business meeting, or you just want to look sharp for date night, these shoes are your go-to. You’ve got a few styles to pick from: Oxfords, Brogues, Derbies, and Loafers. Each has its own vibe, so let’s figure out what’s what.

Why Dress Shoes Actually Matter

Here’s the deal: shoes are like the secret weapon of your wardrobe. You can be wearing a killer suit, but if your shoes look like they’ve seen better days, it’s game over. Quality dress shoes say, "I’ve got this," without you having to say a word. They’re all about making that solid first impression. You know the one that makes your boss think you're ready for a promotion or your date wonder if you’re secretly James Bond? Yeah, that kind.

The Breakdown: How to Pick the Perfect Pair

Hawes & Curtis Dark Brown Leather Double Monk Strap Shoe.

1. Know Your Styles—Because Not All Dress Shoes Are the Same

It’s easy to think, "Shoes are shoes," but there’s a little more to it than that. Let’s do a quick run-down:

• Oxfords: These are your power shoes. Closed lacing, sleek design—think of them as the suit-and-tie of shoes. Perfect for weddings, job interviews, or anytime you need to be on your A-game.

• Brogues: You’ll recognize these by their fancy little perforations (basically, stylish holes). They’re a notch down from Oxfords on the formality scale but still sharp enough for most occasions.

• Derbies: With an open lacing system, Derbies are more relaxed than Oxfords. They’re versatile—think of them as the smart-casual option. You can wear them with a suit or jeans and still look on point.

• Loafers: No laces, no fuss. Loafers give off that laid-back, polished vibe, perfect for smart-casual events or days when you just want to look effortlessly cool.

2. Material Matters—Leather, Suede, and Everything in Between

Crockett & Jones WestbourneDark Brown Calf Suede.

When it comes to dress shoes, quality leather is where it’s at. Look for calfskin if you want that smooth, luxurious feel. Not a fan of shine? Suede is your guy, but heads up—it’s a bit high maintenance, like that one friend who always needs help moving. Just know that suede looks killer but needs extra TLC to stay looking fresh.

3. Focus on Fit—Don’t Squeeze into a Size That Doesn’t Work

Here’s a pro tip: no matter how good a pair of shoes looks, if they don’t fit right, they’re going to ruin your day. You don’t want to be that guy hobbling around a wedding because your shoes are a half-size too small. Make sure your toes have room to breathe, but your heel shouldn’t be sliding around. If it’s a choice between style and comfort, trust me—comfort wins every time. Your feet will thank you.

4. Color Choices—It’s Not Just About Black

Yes, black dress shoes are classic, and you really can’t go wrong there. But don’t sleep on brown shoes—they’re more versatile than you’d think. A nice pair of dark brown shoes can work for everything from business meetings to a casual dinner out. Want to stand out a bit? Try something in burgundy or oxblood. They’re like the cool cousin of black shoes—sophisticated but with a little more personality.

5. Comfort—Because You’ve Got a Long Day Ahead

Remember, style is important, but if your feet are killing you halfway through an event, it’s game over. Look for cushioned insoles or arch support to keep you comfy, especially if you’re on your feet for a while. Pro tip: leather lining can help with that gross foot sweat situation. Some dress shoes even come with rubber soles these days—just make sure they don’t look too casual for the occasion. Comfort and style don’t have to be mortal enemies.

6. Invest in Quality—Think Long-Term

Berluti Equilibre Leather Oxford.

Here’s the thing about dress shoes: you get what you pay for. A well-made pair might cost you a bit upfront, but they’re going to last for years if you take care of them. Look for shoes with Goodyear welt construction (it’s basically a fancy way of saying they’re built to last and can be resoled). That higher price tag is worth it when you’re still rocking them five years later.

Keeping Your Shoes Looking Sharp

So, you’ve found the perfect pair of shoes—now what? Maintenance, my friend. Here’s how to keep them looking as good as the day you bought them:

• Polish them regularly. Think of it like giving your shoes a spa day. It keeps them looking shiny and protects the leather from wear.

• Use crease guards. These bad boys help your shoes keep their shape and absorb moisture (yeah, feet sweat—let’s not pretend they don’t). We like the Diagonal One crease guards because their design fits any type of dress shoe.

• Rotate your shoes. Don’t wear the same pair every day. Give them time to breathe and recover, and they’ll last way longer.

• Waterproof them. Leather and water aren’t friends. Give your shoes a quick spray with a water-repellent product to protect them from unexpected downpours.

Conclusion: Find Your Perfect Pair

At the end of the day, finding the right pair of dress shoes is about nailing that balance between style, comfort, and quality. Get the fit right, pick a style that works for your wardrobe, and take care of them once you’ve got them. It’s not rocket science, but it does take a little thought. And trust me, once you’ve got that perfect pair, you’ll wonder how you ever survived without them.