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written by Zach Weiss — October 22, 2016

Building the perfect wardrobe starts from the ground up. You’ve already given your sock drawer a makeover, now it’s time you started thinking about your next step— literally. Upping your sock game will only take you so far if you’re still pairing your new socks with a busted pair of tennis shoes.


Whether you’re letting loose with the bold designs from our Wild Child collection, or keeping it classy with the classics from the Exec line, here are the shoes that will take you from sad to swag.

1. Oxford

If you’re paying attention, you’ve probably seen a pair of oxfords around before. The Oxford is the utility player every guy will be happy to have waiting at the back of their closet. When the Oxford is used responsibly, it will fit right in at the office or at happy hour a few hours later. They don’t call it a classic for nothing.

Pair it with: Studies have shown that the oxford, paired with the argyle socks from our Luminary V collection, are guaranteed to make you look smarter than you actually are.

We like: Zara offers a versatile, no-nonesense shoe in its Tailored Oxford. 

2. Boat shoe

Don’t let the name intimidate you. You don’t actually need a boat to look great in a pair of boat shoes. Conventional wisdom may say a pair of socks has no business cavorting with a shoe designed for the deck of a ship, but we disagree. Paired with the socks from one of our collections, your boat shoes will find a comfortable home in your office too. Besides, who ever wanted to be conventional?

Pair it with: You’re already bucking convention. Why not grab a pair fashionably outrageous socks from our Wild Child collection and see where your day takes you.

We like: Impeccably made with 100% leather, the Sperry's topsiders are durable, comfortable and look great. There's a reason these guys are #1. 

3. Sneaker

Hold up—We know what you’re thinking. But an on-point sneaker is nowhere near the same as those ratty tennis shoes we just convinced you to throw out a couple of paragraphs up. While it’s true that sneakers aren’t as versatile as the other entries on this list, the phrase “all work and no play makes Jack a dull boy” was probably coined about a guy named Jack who didn’t own any trendy sneakers in his shoe collection. Don’t be Jack. Just get the sneakers.

Pair it with: If the sneaker is already out of your comfort zone, tone it down with the simple-but-still-cool socks in our Exec VII pack. If you’re itching to take it to another level of “fun,” lean in with the crazy socks in our Avantgarde pack.

We like: Who says there's no such thing as a comeback? We recommend checking out the clean design of Pony's Topstar Hi Empire sneaker. 

4. Derby

So you’re serious about being the best dressed guy you know? Then let’s talk about the derby. Contrary to everything you know about the english language, this shoe is somehow both sleek and sharp. It doesn’t care about words or their meanings, it just cares about making you look good. Truth be told, it probably doesn’t care about anything. It’s a shoe.

Pair it with: Now is not the time to reinvent the wheel— you’ve got a cocktail party to get to. Go with the best men’s dress socks in our Exec VI. There’s still enough color there to keep you awake.

We Like: It doesn't get more classic than Allen Edmonds' Flatiron Derby shoe. 

5. Loafer


Comfort met sophistication and decided to create the loafer. Or so the legend goes. Believe what you want— the proof is right there in front of you. A great pair of loafers will keep your feet comfortable as you jet from meeting to meeting without losing you any street cred as the “classy guy” in your office.

Pair it with: Keep it simple and classic with our original Exec socks.

We like: Lean into your wild side with Steve Madden's Caviar loafer.