I recently had a great lunch meeting with a friend who wanted to overhaul his wardrobe from the ground up. He had picked up on what I was doing, and wanted to get into a tailored look with custom suits, classic dress shirts and good shoes. To start, he wanted to keep things very simple and then expand his sartorial horizons once he got his sea legs. I was extremely flattered that he saw me as a good source for counsel. Not only was I happy to help, but I saw this as a personal opportunity to refresh my perspective on solid foundational essentials, dialing it back to the very basics.

In today’s men’s wear culture, it’s so easy to get caught up in what’s hot and so very right now while ignoring the ever-important basics. One might have the wardrobe to look super fantastic in a nightclub, at a fashion show, at Pitti Uomo or at a selvedge denim flea market packed with bearded bros, but put some of those guys at a wedding, an important business meeting or at the occasional black tie affair and they often look like they’re in the wrong room. At funerals, such sartorial illiteracy even looks disrespectful. It’s like having a collection of unique ornaments, glittering tinsel garland and flashing lights but no tree. It goes back to having the basics, which starts with shoes.

Good, well-made shoes for the long game are an investment. They’re the kind of shoes that can calmly and confidently stand in place trend-transcendent while current designer shoes desperately try to outrun and outfabulous each other. These classic shoes rarely if ever appear on “Shoes You Must Have This Fall” kinds of lists. They’re never “in.” They’re never “out.” They are, rather, “above.” They’re constant.

The basics I’m talking about are not only classic and handsome, but they’re also versatile. They can be worn with the sharpest of suits, a nice pair of chinos or a good pair of jeans (though not with black tie). I’ve even seem some brave souls wear them with shorts, but I personally wouldn’t go that far.

With respect to color, the darker the better at first, in my humble opinion. The darker colors are generally more versatile, going with more and giving a bigger bang for the buck, whereas lighter colors are more specific. Once a man has his bases covered with basic black and dark brown or burgundy, only then would I branch out into lighter shades and more adventurous designs of the moment.

The shoes I’m suggesting have several things in common. They’re classic, trend-proof designs that have stuck around for decades. They’re made with something called Goodyear welt construction – a mark of superlative shoemaking that makes the replacement of the sole much easier and extends the life of the shoes. These shoes are also made with top-grain leather (really good), full-grain leather (great) or shell cordovan (fabulous). When you see the words “genuine leather” in a product description, it’s certainly leather but not necessarily good leather. With respect to brand, the ones I’m citing here happen to be American companies: Alden, Allen Edmonds and Florsheim. Other fine shoemakers from the UK who make exquisitely crafted shoes like this are Church’s, Crockett & Jones and Grenson.

Now the shoes…

Plain Toe Bluchers

By definition, a “blucher” is a shoe with a vamp made of one piece of leather. The plain toe varietal is such a simple and versatile design that can go with nearly everything. Sleek and timeless with a little bit of mystery.

Wingtips or “Brogues”

The decorative perforations that make wingtips wingtips are called “broguing,” hence the term brogues. Full brogues have broguing over the cap of the shoe, terminating near the ball of the foot, with additional broguing happening on the back of the shoe. The most common brogues might be the “long wing” brogues, which feature broguing over the cap that extends the length of the shoe along the side, all the way to the seam at the heel (like the ones pictured above). And those two-tone white-on-black/brown brogues popular among distinguished dandies are called “spectator shoes.” I have more brogues than any other style of shoe, with pairs in black, tumbled or “pebble grain” black, burgundy and brown. I’m a huge fan.

Chukka Boots

Chukka boots are almost like plain toe oxfords in ankle boot form. They usually have two or three eyelets for laces and are, perhaps, my favorite shoes in the world. The ankle height is not too high for summer months, but it adds a little something in the colder months of the year. A popular casual-only variation is the suede Clark’s Desert Boot with the rubber crepe sole.

All of these shoes are most commonly made with leather soles, but versions with rubber soles are also widely available.

Honorable mentions…

Monk Strap
Monk Straps/Double Monk straps. I like them, but they’re not my absolute favorites. For my own taste, monk straps are a slightly busy shoe. Double monk straps are doubly busy. I’m not crazy about hardware on a dress shoe. That’s not to say I wouldn’t consider a handsome pair one day, but they’re not high on my list.

Cap Toe
Cap toes. Cap toes often wind up on lists of men’s shoe essentials. I agree… sort of. Aesthetically, I do like them. But to me, cap toes are limited to dressier suited looks. I can’t see them with jeans.

Loafers. Loafers aren’t really dress shoes. They certainly have a place in our wardrobes, but they are casual and not really appropriate for business, serious dressing or any formal occasion, though many men wear them regardless. There’s an old cheeky adage that many grandfathers have imparted to us: Never do business with a man in loafers. Those are playful words in a super-casual culture addled by an endangered sense of occasion, but the words are meant as a warning about one’s seriousness and respect (or lack thereof).

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Some of these shoes may seem prohibitively expensive, but we get what we pay for with shoes. Good shoes are an investment. The leather quality and craftsmanship from the likes of Aldo or Cole Haan do not hold a candle to heritage brands whose lifeblood is superlative boot making. I wouldn’t really trust designer brands, either. High quality shoe craft is not necessarily in their DNA. I once bought a pair of $300 long wingtips from a popular men’s brand that looked and seemed like a more affordable alternative to something like $600 long wingtips from Alden. In the end, the leather was no comparison, the construction was uncomfortably stiff and the purchase was ultimately not worth it. Play it cheap or play the trends, and you wind up with shoes that won’t last very long – physically or aesthetically. What seems like a bargain now will likely end up kicking you in the ass sooner rather than later. As a wise friend once told me: value is quality over time.

With proper care, good shoes will last a lifetime. Good maintenance includes regular cleaning, conditioning and shining, cedar shoe trees and well-tended heels and soles. With my own shoes and boots, the very first thing I do with a new pair is take them to the cobbler for plastic taps under the toes and heels, which drastically reduces the wear and tear of the heels and soles and, thus, preserves their appearance quite effectively. Instead of an $80 re-sole every year, I just get the taps replaced every few months for about $4/pair, extending the life of the soles and heels by years.


There are other essential shoes that other men may prefer. These are just the ones I consider to be core basics and they’ve treated me extremely well. I’m not a sartorial screamer who likes to draw attention to his feet or ankles (more about socks in another post). In my opinion, these are distinctly masculine, unfussy and sophisticated shoes that lend an elegant understatement for a discerning wearer who appreciates quality and cares about the smaller details.

Something work well for you? Hit me in the comments section below or on Twitter or Facebook.

Thanks for reading!