Ever seen a well-dressed man wearing some tired old kicks? Nope? Us either. As designer Hardy Amies said, “It is totally impossible to be well-dressed in cheap shoes.” We agree. So do the ladies. Many women consider a man’s shoes the most important thing he wears. (Did you hear that, single guys?) Neglecting this part of your wardrobe can make you into the style equivalent of the guy at the gym who only works his upper body and ends up with a barrel chest and scrawny legs.
Some guys might build a shoe wardrobe by going to the nearest department store, finding the shoe section and saying, “give me one of everything.” Not you, though. You know that true style isn’t a game of who can drop the most cash on the trendiest stuff the quickest. It’s about finding the timeless pieces and wearing them with panache. That’s why we’ve compiled a handy guide to help you in your quest to build the ultimate dress shoe wardrobe.
To begin, we think the most important shoes any well-dressed gent should have in his arsenal are…(drum roll, please):
1) Brown Brogues
Brown brogues are the jack-of-all-trades of shoes. There’s something almost spiritual about a fine pair of brown brogues. The leather should feel soft and supple, but not too smooth. If you gently run your fingernail across the surface, you should just barely be able to feel the skin’s natural grain. The color should be deep and rich. You’ll instantly feel manlier when you step into them, and you probably won’t want to take them off for a good while. When you finally do take them off, you’ll want to take care of them, because a well made pair will last for a long, long time, and they’ll only get better with age.
Keep them sleek and they can easily be worn with your workhorse navy and gray suits, while the brogueing (the decorative punching on the toes and seams that gives these shoes their name) makes them casual enough to wear with chinos or jeans. It’s hard to find something that doesn’t look good alongside a pair of brown brogues, so we suggest making them the foundation of your shoe wardrobe.
Our Picks – Brown Brogues:
- Charles Tyrwhitt tan contemporary calf brogues, $250
- Allen Edmonds McAllister wingtip oxfords in merlot burnished calf, $345 (pictured above)
- Alden Longwing bluchers in dark brown calf, $523
At some point, you’ll need a pair of black cap-toe oxfords. Someone you know will get married. Or maybe you’ll try to beat a traffic ticket in court. Perhaps you’ll have a job interview. A pair of black cap-toes will be there for you in your time of need. Wear them to any formal occasion. Or, if you work in a conservative environment, you can wear these shoes every day of the week.
Black cap-toes are what we like to call NFA (“Not Fucking Around”) shoes. Since these shoes are limited to somewhat formal use, they lose a few points on versatility and come down our list of essential dress shoes to the number two spot. Still, they’re a key part of any man’s footwear lineup.
Our Picks – Black Cap-toe Oxfords:
- Andrew Lock black oxfords, $250
- Loake Rothschild black cap-toe oxfords, $300 (pictured above)
- Alfred Sargent Armfield oxfords in black calfskin, $725
Brown brogues and black cap-toes are the Lennon and McCartney of shoes. Sure, Ringo’s fun, but with brown brogues and black cap-toes you’re pretty much covered. From here, consider picking up a couple variations on what we’ve listed above. For instance, you can’t go wrong with a sleek burgundy cap-toe, or a streamlined black derby. With two pairs of brown and two pairs of black, you’ve got yourself a solid shoe wardrobe.
So, where do you go from here? It depends on your personal style and how you plan to wear your shoes. Owning all brown and black shoes doesn’t make you unimaginative. Lots of stylish men do just fine with nothing but brown and black oxfords and derbies in their closets. But we understand the desire to branch out. With so many awesome shoes out there, it would be a shame not to snatch up a few pairs. Here are some ideas:
Wholecuts are made from a single piece of flawless leather. Most shoes are made from several pieces of leather because the skins that are used to create shoe leather must be completely free of marks and blemishes. As you can imagine, it’s pretty difficult to find a large patch of skin without markings of any kind. (Look at your own skin. You probably can’t go that far without seeing some kind of mark or discoloration.) So, it’s much easier to find smaller pieces of unblemished leather and sew them together to create a shoe.
Because the hides necessary to create them are so rare, wholecuts are more expensive than their more mundane cousins. But hot damn, just look at these things! Is there anything more elegant than a wholecut? In case you were wondering, the answer is “no.”
Our Picks – Wholecuts:
- Meermin Linea Maestro wholecuts in black Freudenburg calf, $335
- J. FitzPatrick Footwear Tony in deep merlot calf, $484
- Crockett & Jones Weymouth in dark brown antique calf, $810 (pictured above)
4) Monk Straps:
Monk straps are shoes that fasten with straps across the top, instead of laces. They have can have any number of straps: one is common and two is fashion-forward, any more is a bit excessive (unless it’s a boot). Though they have been hot in recent years, monk straps are classics. Traditionally, they’re less formal than oxfords, so if you work in a laid-back office, consider picking up a pair for work. Even in the most starched-shirt workplace, a pair of black single-strap monk straps will allow you to add a little dash to your personal style without making you look too cool for school.
Our Picks – Monk Straps
- Shipton & Heneage Itchin in black calf, $240
- Howard Yount Double Monk Strap in antiqued cognac brown calf, $349
- Herring Raleigh in espresso calf, $597 (pictured above)
Loafers (also known as slip-ons) get a bad rap. They’re often called the lazy man’s shoe and many old school men’s style aficionados argue that slip-ons are too casual to wear with suits. Sorry grandpa, but we’re gonna have to push back on this one. The way we see it, it’s the man wearing the shoe who determines if a combination is elegant. As with your other shoes, the more streamlined they are, the dressier loafers become. Tassels are completely optional (and not necessary in our opinion).
Our Picks – Loafers:
- Ed Et Al Somerset loafers in chestnut brown, $310
- Kent Wang handgrade penny loafer in medium brown, $450 (pictured above)
- Paul Stuart Mervin loafers in beechnut calfskin, $628
There you have it. Follow these guidelines and you’ll be well on your way to amassing one badass shoe collection. With shoes like the ones we’ve listed above, you’ll always be kickin’ it (or NFA) in style.
Got a question to ask us on building a dress shoe wardrobe? Leave a comment for us below!