The Basics: Shoes

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: dissertation extension lse https://recyclesmartma.org/physician/cialis-cusseta/91/ cheap write my essay essay the art of living essay on my country pakistan in sindhi online paper writing service help me to write a business plan citizenship coursework help effect essay about pollution introduction to using aplia assignments here http://www.chesszone.org/lib/proofreading-rates-per-page-4826.html watch click follow follow url get link research techniques test undergraduate thesis examples pdf term paper about minimalism university assignment structure https://nebraskaortho.com/docmed/du-viagra-pour-jeunes/73/ sample papers to edit here https://raseproject.org/treat/viagra-pill-box/97/ click here https://recyclesmartma.org/physician/tomar-cialis-y-alcohol/91/ thesis help online essay on we are the world schaffer essay bbc schools homework help i need help with my algebra 1 homework 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. These shoes are 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. With shoes like these, deciding what socks you wear with them is just as important. Just like shoes, socks can add that little bit extra to any outfit. You may go for standard black or white socks if a classic look is what you’re after. Or you may decide to put your photo on socks to add a fun statement to your outfit. This way, people may be drawn to your socks and then look at the shoes too! It’s a win win situation. 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).

* * *

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!



  1. Looking to up my shoe game in the future … this post will make for good reading again when the time comes to shop for them. Thanks!

  2. I wear these types of shoes often with plain toes being my absolute favorite with wing tip blutchers being my next best favorite. I like cap toes too but loafers I rarely wear. A great read indeed.

    • George Reply

      Love those Gucci horse bit loafers, but I didn’t include them because they’re definitely a more casual shoe and they don’t really have the versatility of a plain toe oxford, a wing tip or a chukka. BUT don’t get me wrong: they’re fabulous.

  3. On plastic tabs vs. rubber sole: after a short wear in-period I always take my shoes to the cobbler to put rubber soles on the heels AND the whole front. Therefore, not much of a leather sole feel is left. Wrong? Breathability is still good!

  4. I’m a Johnston & Murphy black cap toe man! No mention of J&M. In my opinion – the best out there!

  5. After watching the clip on the initial purchase of your black Florsheim Imperial Kenmoor wingtips, I would love to see a follow-up in the fit and wear of them. I’m contemplating buying a pair myself but maybe in the plain toe. -B

  6. I was seriously holding back my wardrobe (made-to-measure suits) with bad shoes. It wasn’t until a pair of Crocket and Jones Oxfords that I saw the light. And hallelujah! What a difference it makes to the overall look. I’d say my “suits” (it’s really the whole look) is 200% on what it was.

    “I’m not a sartorial screamer who likes to draw attention to his feet or ankles” – in fact according to the guides I’ve read, quite the opposite. Menswear should draw attention *away* from the ungainly looking feet and legs of male anatomy. Away and upwards towards your face.

  7. Long-time reader, infrequent commenter: As an alternative to taps, I invest in rubber soles under the toes and heel. Certainly more expensive than taps, but they also add durability and comfort.

    It is also important to stress that a new pair of brogues, boots, bluchers is stiff and hard to get your foot in. A shoehorn should be used to slip your foot into the shoe to avoid threatening the craftsmanship of the footwear. Over time the shoe is easier to get on, but I think it is a good practice to keep a shoehorn nearby.

    Finally, realizing that the post is pitched as an introduction to shoes, I wonder if you have an opinion on wearing colored laces. I received a few pairs of colored laces from Hook and Albert and enjoy the ‘pop’ of color they add to the shoe.

  8. George, I like the MacNeil’s. I’m having trouble deciding on the oxblood or the dark chili. Do you have a preference?

    • Great shoes. Tough color choice. If you already have dark brown dress shoes, maybe oxblood. It has a little red in it. But if you need your first brown wingtip, go chili.

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