34 Coolest Men’s Fashion Shoes on the Market

It is a well-known stereotype that women love shoes. Like, “own 12 pairs of black pumps that to the untrained eye all look exactly the same” kind of stereotype. And while stereotypes are that way for a reason, the fact that men are left out of this is just simply untrue. How many sneakerheads do you know that own less than 10 pairs? Or your fashionable neighbor who seems to be in a different pair of casual boots or loafers almost every day? 

If you are the guy with a couple pairs of sneakers, one pair of boots, a casual dress shoe, and one pair of black formal shoes way, way in the back of your closet, keep reading. It is time to up your shoe game, my friend.

1. Boots

Chelsea boots, ankle boots, motorcycle boots, Chukka boots, dress boots, cowboy boots… I could keep going but I digress. The point is that there is a boot for everybody, every occasion, and every style. 

Going hiking? There’s a boot for that. If you choose well, you can double up and your hiking boots can also be your favorite casual boots. Feeling a little rock-n-roll today? Pull on those bad-ass motorcycle boots over your black skinny jeans, your favorite worn-in t-shirt, wrap a bandana around your neck or wrist, and go forth and make that girl yours (while letting her maintain her sense of individuality and knowing she is free to do whatever she chooses. Respect. It’s 2021, after all. She is a strong, independent woman).

Again, I digress. Boots are an all-encompassing shoe. There is a boot style that covers the gamut of work casual (Clarks ankle boots for the win) to your favorite streetwear look (hello, Timberlands) to the boot that keeps getting better with age (I’m talking to you Thursday Boot Company).

2. Casual

While a lot of people are still working from home, that doesn’t mean that they aren’t going out in public and taking meetings in person. Then there are those of you that are back at the office. Going from work to drinks to dinner can sometimes be the itinerary for the day and your look, and shoes, need to work for all three events. Business casual can encompass several different shoe styles including boots, loafers, and sneakers. 

Try the Clarks Desert boot for a smart-looking boot that looks just as effortless with jeans as with chinos. Buy them in a neutral or shade of brown to make them as versatile as possible.

Looking for a dressed-up pair of kicks? That’s good. Wearing your Jordans to the office isn’t usually the move unless you work in a very casual work environment and then more power to you. For the rest of us, try Stepney Workers Club Dellow leather sneakers. Not only do they look high-end and again, look great with jeans and ankle pants, but these leather sneakers are under $100. Buy multiples.

3. Formal

There comes a time in every man’s life when he is going to be invited to a formal event, whether it’s for work, for a friend, or himself (like your own wedding, for example). Now, there is casual formal and formal formal (the latter is usually referred to as “black tie”) and they require different shoes.

For a casual formal event, you will most likely be wearing a full suit or a combination of chinos, button up shirt, and a blazer (a tie may or may not be optional). The Allen Edmonds Bond Street Cap-Toe Oxford is a sexy shoe that would look fantastic for just about any formal occasion. Except black-tie. ​​There are four commonly accepted shoes that are considered appropriate for black tie ensembles: opera pumps, Oxfords, Venetian loaders, and slippers (sometimes called Prince Albert slippers). Choose your poison.

4. High Top

Calling all sneakerheads! This is your time to shine! So many high tops to choose from. Air Jordan 1, a Chuck Taylor, or a Vans Sk8-Hi is never the wrong move. High tops never go out of style and they work with so many looks, stylistically. Throw on some slim joggers and a hoodie or oversized ankle pants with a t-shirt and denim jacket. You really can’t go wrong with this style of shoe. Heading for a casual day about town with your girlfriend? High tops. Grabbing drinks with the boys on Saturday? High tops. Running errands? High tops.

5. Italian

Nothing says you have style like a pair of luxurious Italian shoes. Oxfords, loafers, sneakers… there’s nothing that some fine Italian leather and craftsmanship can’t make better. Sure, these shoes may be an investment (yes, I will take the Ambrogio Bespoke Men’s Handmade Custom Shoes Tobacco Brown Patina Leather Oxfords for $650 Alex) but you will have these shoes forever. Literally. Ask to be buried in them. Luxury Italian leather only gets better with age and wear, so coming up for occasions to wear them might be the most difficult, or the easiest, part of this whole thing.

6. Loafer

Loafers are like a slipper that you can wear outside without judgment. They can be dressed up or dressed down. Wear them to church or to run a quick errand. Throw on a pair with chinos and a button down for instant sophistication. Also referred to as penny loafers or drivers, this shoe style comes in a variety of materials and fabrics; velvet, leather, suede, you name it. Are you a little more on the edgier side? Not to worry, Dr. Martens has you covered with their with a chunky sole, tassels, and kiltie (which is a fringed leather tongue). Fancy.

7. Sneaker

We have written countless articles on sneakers and will continue to, of course. Sneakers are the most basic shoe that should be in every man’s wardrobe. There are sneakers for actually working out, sneakers strictly for fashion purposes, and then there’s the whole sneakerhead universe. We’ll save workout shoes and the cut-throat world of sneaker fandom for another day. For today, I bring you fashionable sneakers. Typically, what this means is a basic shoe made of not-so-basic materials. Instead of throwing on a canvas Converse, put on a leather (or vegan leather) Adidas Stan Smith with your ankle pants and button up or polo. Smart, casual, classic. 

Looking for something a little more high-end, and not white? Try the Tom Ford Midnight Blue Warwick Suede sneaker. They work with your khaki shorts and t-shirt for Saturday’s BBQ as well as for Monday’s lunch meeting, worn with chinos and a blazer.

8. Suit

Depending on the cut, style, and occasion, almost all of the above shoes can be styled with a suit. An Oxford or loafer looks great with a classic suit with straight legs and a matching pants/blazer combo. 

Making your own suiting with your favorite new ankle pants, vest, and button-down? White leather low tops are always a crowd favorite, but loafers and oxfords are also not wrong here. Just don’t show your socks if your ankles are exposed. Fashion faux pas.

9. White

Clean, classic, and versatile. Stan Smiths and low top Nike Air Force 1’s are the go-to white sneakers to wear with jeans, ankle pants, slim casual suits, and shorts, but just about every brand has its own version of these silhouettes. 

A pair of Common Projects Bball leather sneakers are elevated in style and in price, but always look great and will last. Looking for something a little different? White Jibs mid-rise easily slip on for comfort and style. More of a boot person? Dr. Martens white lace-up boots will elevate any standard rocker or 90s look.

Conclusion

So many shoes, so little time! Don’t know where to begin? I would start with a clean white sneaker that can be worn with a variety of looks. Next up, an oxford or loafer for those dressier occasions, followed by a pair of boots of the combat variety. Now that you have a shoe for every style, you can start building out from there. Do you wear a lot of business casual looks? Maybe start by building out Italian shoes, oxfords, and loafers. Are you more rugged and out and about? Start collecting various boot styles. Keep in mind, buying something on-trend is fine occasionally, but spending more money on a classic style that is well-made will serve you better in the long run.