You’re standing in front of a closet full of options, yet somehow, you still feel like you have nothing to wear. It’s a classic problem. Most guys think they need twenty pairs of footwear to be "stylish," but honestly, you probably only need five. If those five are the right types of mens shoes, you can navigate a wedding in Tuscany or a rainy Tuesday at the office without looking like an amateur.
The shoe industry is basically a minefield of marketing jargon. Brands throw around terms like "genuine leather" to make cheap materials sound premium. Spoiler: it’s not. "Genuine" is often the lowest grade of real leather you can buy. If you want something that lasts longer than a single season, you have to look deeper into the construction—things like Goodyear welts and Blake stitching—rather than just the logo on the insole.
The Formal Heavy Hitters
Let’s talk about the Oxford. It is the undisputed king of formal footwear. You can spot a true Oxford by its closed lacing system. This means the eyelet tabs are sewn under the vamp. It’s sleek. It’s stiff. It’s what you wear when the invite says "Black Tie" or you’re trying to close a massive business deal.
Then there’s the Derby. People mix these up constantly. The Derby uses an open lacing system where the tabs are sewn on top of the vamp. It’s a bit more "chunkier" and significantly more comfortable if you have a high instep. If the Oxford is a tuxedo, the Derby is a well-tailored navy suit.
Why the Brogue Isn’t Actually a "Type"
Here is a hill I will die on: a brogue is not a shoe type. It’s a decoration. You can have an Oxford brogue or a Derby brogue. Those little holes? They were originally designed for Irish farmers to let bog water drain out of their shoes. Now, they’re just for aesthetics.
The more "broguing" a shoe has, the less formal it is. A full wingtip brogue is great for a casual Friday, but it might be a bit much for a funeral. Stick to a cap-toe Oxford for the truly somber or ultra-professional moments.
Boots That Actually Do Something
Most guys buy boots because they look cool, but different types of mens shoes in the boot category serve wildly different masters. Take the Chelsea boot. No laces. Just elastic side panels. They’ve been around since Queen Victoria’s shoemaker, J. Sparkes-Hall, patented the design in 1851. They gained massive fame in the 1960s with The Beatles. They are the ultimate "cheat code" for style because they look just as good with slim denim as they do with a suit.
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Then you have the Chukka. These are ankle-high with usually only two or three pairs of eyelets. If you get them in suede, they’re often called Desert Boots. Nathan Clark (of Clarks fame) saw these in a bazaar in Cairo during WWII. They’re rugged but lightweight. Perfect for when a sneaker feels too young but a dress shoe feels too stuffy.
- The Combat/Work Boot: Think Red Wing or Dr. Martens. These are built for abuse.
- The Jodhpur: Similar to a Chelsea but with a strap and buckle. Very "rock and roll" if you can pull it off.
- The Service Boot: A standard lace-up boot modeled after military footwear from the early 20th century.
The Loafer Spectrum
Loafers are misunderstood. Some people think they’re "grandpa shoes," while others think they’re only for people who own yachts. The reality is that the Penny Loafer is the workhorse of the modern wardrobe. G.H. Bass created the original "Weejun" in the 1930s. The name comes from "Norwegian," as the design was inspired by a Norwegian farm shoe.
The "Penny" part? That came from students in the 1950s stuffing a coin into the leather slit on the saddle. It’s iconic.
If you want to go more formal, the Horsebit loafer is the move. Gucci popularized this in 1953. It features a metal bar across the front that looks like a horse’s bit. It’s bold. It’s expensive. It tells everyone in the room that you’re doing just fine. On the other end, you have the Tassel loafer. It’s a bit more academic and "trad." It was actually created after an actor named Paul Lukas asked two different shoemakers to create a version of a shoe he’d found in Europe.
Sneakers: Not Just for the Gym Anymore
The rise of the "minimalist sneaker" changed everything. Before Common Projects released the Achilles Low in 2004, you didn't really wear sneakers with a suit. Now, a clean, white leather low-top is a staple of the types of mens shoes every guy needs.
But watch out for the "Dad Shoe" trend. Chunky soles and neon colors are fun, but they age poorly. If you're investing in quality, stick to the classics.
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- Canvas Low-Tops: Think Chuck Taylors or Vans. Cheap, breathable, timeless.
- Athletic Trainers: Specifically for performance. Don't wear your running shoes to a dinner date unless you're actually running to the restaurant.
- Luxury Leather Sneakers: These are made with the same leather as dress shoes. They can be resoled in some cases, which is rare for a sneaker.
Material Matters (More Than You Think)
Leather isn't just leather.
Full-grain leather is the gold standard. It hasn't been sanded or buffed to remove "imperfections." It’s the toughest part of the hide. It develops a patina over time. If you see "Top-grain," it means the top layer has been sanded off to hide scars. It’s thinner and won't last as long.
Then there’s Suede. It’s the underside of the skin. It’s soft, porous, and hates rain. If you live in Seattle or London, you better have a can of protector spray handy. Nubuck is similar to suede but created from the outside of the hide, making it a bit more durable but still velvety.
Construction: The Secret Sauce
If you want to know if a shoe is worth $300, look at the sole.
A Goodyear Welt involves a strip of leather (the welt) being sewn to the upper and the insole. Then, the sole is sewn to the welt. This makes the shoe water-resistant and, more importantly, easy to resole. You can keep a Goodyear-welted shoe for twenty years if you take care of the leather.
Blake Stitching is different. The outer sole is stitched directly to the insole. This makes the shoe more flexible and lightweight. It’s common in Italian shoemaking. It’s sleeker, but water can sometimes seep through the stitches more easily than a welted shoe.
Common Misconceptions and Mistakes
Most men buy shoes that are too big. They think a little extra room is "comfortable," but in leather shoes, that leads to excessive creasing and blisters. Leather stretches. It should feel like a firm handshake when you first put it on—not a stranglehold, but definitely not loose.
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Another mistake? Wearing the same pair every single day.
Leather needs time to breathe. It absorbs about a shot glass worth of sweat every day you wear it. If you don't give it 24 hours to dry out, the salt and moisture will rot the leather from the inside out. Use cedar shoe trees. They absorb moisture and keep the shape. Honestly, they’re the best $20 investment you can make for a $200 shoe.
Color Coordination Without Being Weird
Black shoes are for funerals, weddings, and very formal offices. Brown is for everything else.
But "brown" is a wide spectrum. Dark chocolate brown is incredibly versatile. Tan or "cognac" is flashy and draws a lot of attention to your feet. If you’re wearing navy trousers, dark brown is almost always a better choice than black. It provides a softer contrast that looks more sophisticated.
Actionable Steps for Building Your Collection
Instead of buying five pairs of mediocre shoes this year, buy one or two high-quality pairs. Start with a dark brown Chelsea boot or a Penny loafer. These are the most versatile types of mens shoes because they bridge the gap between casual and formal.
- Inspect the grain: If the leather looks like plastic or feels unnaturally smooth and shiny, it’s likely "corrected grain." Avoid it.
- Check the sole: Look for visible stitching on the bottom. If it’s just glued on, the shoe is essentially disposable.
- Invest in maintenance: Buy a horsehair brush, some high-quality cream polish (like Saphir), and cedar shoe trees.
- Rotate your wear: Never wear the same leather shoes two days in a row.
- Know your size: Get measured on a Brannock device at least once as an adult. Your foot size can change over time.
Quality footwear is a long game. It’s about the cost-per-wear, not the sticker price. A $400 pair of boots that lasts ten years is significantly cheaper than a $100 pair you have to replace every twelve months. Plus, they just look better as they age.