04 - 7 Must-have Shoe Styles for a Fashion-Forward Urban Man
A few ideas for starting your shoe collection
My name is Ev, and I’m a shoe addict. And my biggest problem is that I can’t buy them all. It’s neither practical or economically feasible; albeit, I’ve been doing a lot of vintage shoe shopping lately. Maybe too much 🫠
All that made me ponder what would an ideal (read: budget-conscious and practical) shoe collection look for someone like me, a fashion-conscious, male city dweller who find elegance in seemingly incompatible things: rugged Americana, Italian craftsmanship, French design sensibility, Northampton footwear tradition, and the wabi-sabi Japanese aesthetic.
Quite a blend, eh.
So, yes. I gave it a thought, and here’s my highly-opinionated shoe collection checklist. Consider this your starting point :)
#1 The versatile derby (or a fancier oxford)
Derbies are all-rounders. This type of shoes features open-laced design and classic silhouette, which makes it suitable for both casual Fridays and semi-formal meetings.
The elephant in the room, though, is that classic derbies are often a little too understated. Worse yet, wearing them could signal a lack of imagination. We don’t want that.
So, instead of a pair of plain black derbies you can opt for a darker shade of brown leather for versatility, and then dial things up a notch by going with a cap-toe or even a half-brogue.
Why it’s essential: With derbies, you don’t have to think. They pair effortlessly with almost everything from tailored trousers to denim.
Pro tip #1: Look for vegetable-tanned leather. It will develop a unique patina over time and gain a lot of character. (Note though that this will make the shoes skew more toward casual end of the footwear spectrum.)
Pro tip #2: Get a pair of oxfords instead of derbies. By design, oxfords are naturally more formal, which is why they are actually easier to dress down: formal oxfords contrast with casual clothing and thus look more deliberate when it comes to personal style.
And if you’re struggling to incorporate dress shoes into your less formal wardrobe, I gotchu covered:
#2 The minimalist sneaker: fun, but can be dressy
For a cool yet subdued style, go for clean, minimalist leather sneakers in neutral tones. They strike a nice balance between casual and sophisticated, and could work great if you need to dress down a suit or elevate casual denim.
Why it’s essential: Comfortable, stylish, and can be effortlessly cool.
Pro tip #1: Keep them clean! A simple wipe-down after each wear ensures they remain crisp and professional.
Pro tip #2: I’ll get some flak for this, but I encourage you to avoid white sneakers. I once took a short 5 min ride on a streetcar (or a tram, if you’re not from Toronto), and counted nearly 20 people wearing plain white sneakers.
Remember: Minimalism is great. Sameness is not.
#3 The weatherproof service boot
You will get caught in the rain, walk on wet snow, and step into dog poop. (Sorry for being graphic, but I don’t sugarcoat things in this blog.)
You need something to resist the urban gunk. A pair of service boots can do a fantastic job in this department. Opt for something sleek with a commando sole for a good grip without sacrificing style.
Why it’s essential: Service boots are rugged enough for rainy days yet refined enough for a smart-casual dinner. Having a pair is pretty much a no-brainer.
Pro tip: Look for boots with Goodyear welted or stitchdown construction for top-notch durability and waterproofing.
#4 The modern loafer for a spring / summer season
I firmly believe that warm summer nights and cocktail bars exist so you could wear a pair of loafers. They are cozy yet effortlessly chic.
Choose penny loafers in a classic color or tassel loafers for a bit more flair. Or throw all the rules out and get hand-painted loafers with a wild colorful patina. You do you. It’s summer. Have fun.
Why it’s essential: Loafers perfect for those in-between occasions where sneakers feel too casual and Oxfords feel too formal.
Pro tip: Pair them with no-show “footsie” socks for a contemporary look.
#5 The “look at me” brogue
Brogues are casual shoes that pretend being classy, and I love them for that. They occupy a different casual dimension, sitting somewhere on a different plane of shoe existence.
Regardless of what you think of them, brogues command attention.
My favorite thing about them is how easily they elevate almost any otherwise tame getup.
And yes, there’s a bonus point: hardy brogues made from vegetable tanned leather acquire an insane natural patina over time. (Note to self: add an example to this post once I find a worthy exhibit :))))
Why it’s essential: Brogues are guaranteed to get you compliments and turns heads. Skip them only if you don’t enjoy attention :)
Pro tip: Brogues are visually busy. It’s best to keep the rest of your outfit understated when wearing them.
#6 The novelty shoe
This one is for the playful child in you. Novelty shoes are hard to pair with most clothes, but once you nail the look, they are a stunner.
If you’re in North America, some relatively affordable brands are Fluevog and Taft.
Why it’s essential: There’s no better way to express playful personality than to wear fun shoes. That is, if you have something to express 😅
A word of caution: Most novelty shoes in the sub-$500 zone focus on the fashion aspect rather than quality. You will see cheaper construction, lower quality leathers (including mediocre patent leathers), and the shoes will overall have shorter lifespan then the higher-end footwear from the likes of Marc Guyot or Clergerie.
#7 The wildcard
A shoe or a boot that’s both classic and uncommon. Maybe it’s an intriguing shape: Norwegian split toe, monkey boot, moc toe derby, a vintage U-wing brogue. Or maybe it’s an exotic leather: bison, antelope, or even shark or stingray.
The direction you choose to go in depends entirely on the range of your comfort zone and the budget. And while most of us have hard monetary constraints, I encourage you to explore the limits of your stylistic comfort zone when exploring the wildcard pair.
Why it’s essential: The very process of selecting an unusual pair of shoes is fascinating, and it can teach you a lot about the styles you find interesting. Even if you don’t end up buying a pair, this is a great exercise.
Pro tip: Don’t rush into buying this pair. Take it slow and let it simmer by researching options and styles. The worst thing you could do is spend a lot of money on a pair that you don’t really enjoy.
I’ve done that, and it’s always painful.
About Kōbō Mono
Kōbō Mono is a blog about quality boots and shoes.
It’s currently run by one person: me. (Talking about myself in a third person has never felt more odd.)
It’s a place to connect with the fellow footwear enthusiasts, share what I work on, and build a community.
If you like what you read here, please consider subscribing or sharing this post with friends. Your help will go a long way 🙏
And since we’re at it, I want you to know that my long-term dream is to start a shoe company. We’ll see how that goes.
You can read more in the About section here: https://kobomono.substack.com/about