The 8 Styles of Shoe Every Man Must Own
From sneakers to sandals, these are our top eight essential shoe styles.
By: Logan RossDate: 2025-02-06
As the saying goes, you can tell a lot about a man by his shoes. But what might you gather about a man wearing the wrong shoes — or at least, in the entirely wrong scenario?
Contrary to what Mr. Frank Costanza of Seinfeld might say, you shouldn’t wear your sneakers in the pool. Nor should you wear winter boots to a black-tie event. A pair of sandals won't slide on your next high-elevation hike.
The best way to combat any unfavourable footwear fiascos is to have a well-rounded selection of shoes suitable for a wide variety of life’s most exciting (and mundane) scenarios.
We’ve narrowed down the perfect footwear capsule to eight basic styles — here’s what you should always keep on deck.
Simple White Sneakers
It wasn’t long ago when sneakers were exclusively perceived as athletic gear. These days, almost everyone on the street is wearing them. Whether you’re an avid sneakerhead or just need some to wear on the weekend, we always recommend your primary pair be some simple white plimsolls.
Historically speaking, white is the quintessential colour for sneakers, which is convenient as it goes with absolutely everything. Whether you opt for a soft leather, supple suede, or clean canvas, ensure your first pair of white sneakers has a minimal, low-key silhouette that’ll play well with anything from swimwear to tailored suits.
Shiny Black Oxfords
If you had to own one, just one pair of formal shoes, these would be them. The most formal of occasions usually call for black tailoring (like funerals or any time you’re wearing a tuxedo) and with black tailoring we only wear black shoes — never brown.
Simple and sleek in silhouette, oxfords are easily the most discreet (and therefore versatile) style of dress shoe out there. Whether you want your shoes to take more of a starring or supporting role in your outfit, some shined-up black oxfords are up to the task.
Sturdy Dark Brown Derbies
Depending on who you ask, wearing black — especially black tailoring — is only appropriate for a handful of occasions, with funerals being the most common (and the most morbid). If you share a similar perspective, you’ll struggle to find situations where black shoes are the best call.
This is where a pair of brown derbies come in handy. The derby-style shoe, with its open lacing system and more overtly raised eyelets, is slightly less formal than the oxford. Often featuring details like wingtips, toe caps, and broguing, there are a few more casual details that make derbies look less stuffy than oxfords.
For when you want to look dressed up but not necessarily your dressiest, opt for a dark brown derby. From weddings to date nights to job interviews and more, you’ll get more use out of these than you might initially think.
Soft Leather Loafers
In the warmer months, you’ll seldom see us out and about in anything other than some simple leather loafers, whether that means calfskin, suede, or another soft, natural material. And more often than not, we go sockless in them too.
Depending on your dress sense, a pair of loafers loafers might seem more formal than normal. That said, no matter if your personal style proclivities lean more towards dressed-up or dressed-down, there’s a myriad of situations where you need something between a dress shoe and a sneaker.
If you’ve still got a loafers-sized hole in your wardrobe, amend that immediately. Find some in a nice dark brown pair and break them in (wearing socks, at first) around the house. Before long, they’ll be the most comfortable leather shoes in your rotation, guaranteed.
Handsome Dress Boots
In the cooler months, a pair of dressier leather boots essentially take the place of our less robust loafers. When your biggest, baddest pair of boots would be overkill but the forecast still reads scarily close to 0 degrees, these are what you should be wearing.
From jeans and chinos to dress pants and suit trousers, you can wear some handsome leather boots with pretty much anything throughout the Fall/Winter season. No matter if they’re lace-ups, Chelsea boots, chukka boots, or other, just ensure they stay nice and shiny — to some degree, at least!
Rugged Winter Boots
Every Canadian comprehends the innate value a trusty pair of winter boots presents.
Once winter's deep freeze starts, you need to ensure your footing is fit to keep you standing for several straight months. A solid pair of boots offering both warmth and tread (slippery snow and ice are no joke) could very well save your life in the Great White North.
But none of this goes without saying, your winter boots should also look great too. Go for something classically styled with timeless good looks to match any occasion. Though when it comes to production techniques and performance technology, modern applications tend to be better.
Designated Trainers
The aforementioned white sneakers on this list shouldn’t be confused with real trainers. You know, type you’re actually meant to wear when working out.
Every man should have a regular exercise routine and therefore every man should have appropriate footwear to wear while exercising. While form is always appreciated, this particular purchase decision should be motivated primarily by function.
Find a pair that complements the shape of your foot well and, if you’re a runner, your foot strike tendencies (rear, mid, and forefoot strikes require very different sole support). Make sure to try on a few different styles and brands before settling on one pair.
Slides and/or Sandals
The footwear equivalent of Jeff Bridges’ iconic character The Dude, a pair of slides and/or sandals are easily the most casual, carefree shoes on our list of essential styles. With that in mind, however, they’re nonetheless essential to own.
Obviously, these shoes are best suited to the warmer months when airflow around your feet is encouraged. However, there’s never been a stronger moment for the socks and sandals/slides look than the present, which means you can get away with wearing them well into the cooler months too.
Additionally, having a pair of slides or sandals around the house is invaluable, practically speaking. Whether you’re looking for something to wear when taking out the trash, minding the barbecue, or taking the dog for a walk, these are great to have on-hand.
