Shoes speak volumes about you as a person and what you want to do at any given time.
Wearing sneakers? You’re going for a jog.
Wearing wingtips? You’re going to work.
Jogging with wingtips? You’re doing something for your YouTube channel.
But what shoes does a pragmatic, style-conscious gentleman need in his closet?
- Sneaker (Casual)
- Plain toe (Smart Casual)
- Cap toe (Business Formal)
- Derby (Business Formal)
- Oxford (Formal)
- Wingtip (Versatile)
Let’s talk why.
Shoe #1. Sneaker
Sneakers are the casual and workout standard for gents around the planet.
Regardless of how they look, sneakers are designed for comfort above all else. That makes them ideal for doing everything aside from hiking and construction work.
If for no other reason, you should have a pair of sneakers to remind you of two things:
Because sneakers are made for comfort, they’re arguably the best relaxation shoe (boat shoes and sandals aside).
They’re definitely the most socially-acceptable shoe for hitting the gym, though. Even if they weren’t, we’d still recommend using sneakers for any kind of work or exercise purely because they’re safe, too.
The combination of tough treading on the bottom and a comfortable sole give you everything you need to take on a long day.
As a side note, the best sneakers all have arch support that you can feel the moment you slip them on your feet.
Arch support may cost extra from some companies, but it’s absolutely worthwhile. It’s especially important if you’ve ever come home from hiking or sports and felt a dull pain in the bottom center of your foot.
That’s your arch! Take care of it — it plays a big role in helping you stand and balance.
Shoe #2. Plain Toe
Plain toe shoes are the choice footwear for the smart casual style.
“Smart casual” means you’re going somewhere to have fun, but you want to look good while you do it.
As a result, plain toe shoes — and other smart casual footwear — often incorporates simple designs and comfortable soles.
While you don’t want to go running in them, you can wear these shoes out for a night on the town or a family dinner.
You’ll find plain toes on other shoe styles as well, especially formalwear. It’s the standard, smart-looking toe style for leather shoes that go well with suits and tuxedos.
But unless you’re going to a black tie event, you probably won’t need those — yet, anyway.
For the purposes of modern gents, go for a pair of plain toe shoes that feel good and look good with a pair of dark jeans.
Shoe #3. Cap Toe
Cap toe shoes are a little more formal than others. Still, they’re not so formal that you have to reserve them for a suit-and-tie occasion.
Cap toe shoes will look great in almost any modern work environment. Just like plain toe footwear, you can find cap toe shoes for just about any occasion.
Still, the lion’s share are made for business casual or informal attire.
This makes them must-haves for the gents who like to dress up a little bit extra for social occasions. Bar-hopping, birthdays, and family gatherings are all slightly more classy when you roll up with a pair of cap toes.
Pick a pair that goes well with dark jeans, but also keep khakis and even semi-formal dress pants in mind.
Shoe #4. Derby
They’re sleek. They’re smooth. They’re timeless.
Apart from the fact that mine have wrinkles in the toes because I haven’t replaced them in years (shame on me), derby footwear goes perfectly with dress pants.
You can also rock derby shoes with suits, although you probably won’t find many variations made for tuxedos or black-tie events.
All in all, they’re just solid shoes. Expect the sides to be thinner than a lot of other footwear, but find a pair that comes with a comfortable sole.
One of the best things about derby shoes is that they look great and have enough of a sole to make you comfortable, too.
Shoe #5. Oxford
Oxford shoes may be the most commonly-seen shoes for formalwear on this list.
They’re perfect for any occasion that requires a jacket and tie. Fine dining, holidays, impressing your in-laws — you name it.
Oxfords will probably cost the most out of all the shoes on this list, but they’re worth the price. A good pair can last you for a couple of years and dozens of special occasions.
If you dress formally for work, you may wear these every day. In that case, expect to pick up a new pair at least two or three times per year.
But when you wear them sparingly, Oxford shoes can give you a good long life.
If you have to wear them and be on your feet all night, good luck — you’ll feel it that evening.
Shoe #6. Wingtip
I mean, just the best.
Finer casual dress, semi-formal attire, formal suits — everything goes with a good pair of wingtips, provided they’re the right color.
I recommend cognac wingtips above any other color. Cognac footwear is gorgeous to start. When it’s combined with a wingtip shoe, it just looks awesome.
Wear these with jeans, dress pants, khakis, or anything else. The sky is the limit with good wingtips, and you can probably find a pair that’s comfortable to boot (so to speak).
If you don’t have any other pair of shoes on this list, get wingtips first. Try them out and take them for a spin.
When you get the right pair, you’ll wish you could wear wingtips all the time.
Fill Out Your Gentlemanly Footwear
Do you need to pick up one of these shoe essentials?
Like most of the other things we talk about on Gents of Lancaster, you can find all of these shoes on Amazon.
Click the section headings for different shoes or check out the Amazon section for men’s shoes to get your pair!