Sneaker Do’s and Don’ts For Guys: What Kicks You Should Wear For Every Occasion

I get a lot of questions from guys about what kicks they should and should not be wearing. Are there sneaker faux pas, they ask. And the simple answer is yes. But they’re often hard to break down, because it’s more of when you see it you know it. You take one look and you think, no. Absolutely not. But I’m going to try to run through a few basic no’s, and then give some suggestions for kicks you can wear for different situations.

  • No holes. (This one goes out to women too) Seriously. It should go without saying, but for some reason, I have to say it. There’s no reason your sneakers should have holes in them. Why do people wear sneakers with holes? It’s like the entire outfit looks good; crisp shirt, nice jeans, and then you get to the kicks and there are tears in the mesh. You are an adult who has a job! You pay your rent, you pay your bills. I’m sorry. There’s just no excuse. I know it’s not about the money, because I’ve asked. You might be cheap, which is fine,  but you can get cheap sneakers. I’ll find you a pair for less than $50. Just ask me. Skip seamless 2 nights in a row and you’re set. So honestly, it just comes across as lazy. Like you don’t have 20 minutes to sift through a few pairs online and hit order? Lazy is a turn off! Trade them in. Seriously. Chuck em.
  • Time and place. Meaning: wear the right kicks to the right event. If I showed up in spikey heels to your friend’s backyard, beach cookout, you’d probably be like “you look like an idiot”. Same goes for you. Don’t ever wear basketball sneakers unless you’re playing ball, and don’t wear trainers/ workout sneakers on a date. I get it. You work out. That’s awesome. But your worn in running shoes don’t look cute with your outfit. Sneakers are in, yes. But not the ones that have been sweat through so many times, I can see white stains forming salt crust designs around the edge. Unless we’re going to a workout class together. Then it’s totally hot.
  • Know yourself. And by this I mean, I strongly believe anyone can pull off anything if they style it properly and they’re confident. If you carry yourself with confidence, you can pull it off. That being said, don’t go for something super crazy or cool that you saw online, if you’re going to walk around like Michael Cera in Arrested Development wearing them. You got to own it. You know how those New Balance dad sneakers became cool all of a sudden? Well they still look weird on guys who wear them like dads. Make sure you’re pairing your kicks well, and make sure you’re walking with confidence. Trust me it shows. (Fun fact: confidence with fashion and mostly everything is very attractive). But if you’re not there yet, that’s cool! It’s ok to play it safe. Just wear what makes you comfortable! (Within reason— REMINDER: comfortable- does not mean ugly!)
  • Avoid: Sketchers (this should go without saying). Saucony. New Balance (unless you know what you’re doing), Asics (unless you know what you’re doing). When in doubt: stick with Nike and Adidas. They’re your safest bets (although you can even mess up with those).

So now that I tore apart your closet, let me give you some suggestions.

Wear to work:


This Brooklyn based brand is a classic kick you can easily dress up or down. You can wear them with a suit/ blazer situation or with a more casual look. They come in a more casual knit and classic leather versions, and you can’t go wrong with these kicks. If you’re scared to make the jump from work shoes to sneaks, a leather pair of these in black or brown is great option. Plus they have free shipping and returns on all orders, so you’re not locked in.


NikeCourt Royale AC

If your office has more casual vibes, throw on a pair of NikeCourt Royale AC’s. They have professional vibes, but still have the Nike check, so it’s no secret that you’re wearing kicks. They’re $60. They’re affordable. They come in multiple neutral colorways. And they’re classically cool. Pair them with a pair of Jogger style pants like these from Zara, and you’re good to go. This is perfect for a work to date look. Which brings me to….

NikeCourt Royale AC/


Wear on a Date:

We’re going on a date. If it’s the weekend, and we’re doing something casual, let’s have a little more fun.

You’re classic: I get it. You’re type A, and you just can’t take the plunge. Don’t go crazy! Be yourself! Keep it simple. Go with Adidas Stan Smiths or a pair of Vejas. Zara also has cool kicks for affordable prices if you’re interested in clean looks that won’t break the bank. Actually, I just realized, if you’re type A you probably won’t want white kicks. How will you keep them white?! Wear the knit Greats. they’ll look clean and cute. 


Nike React Element 87 or 55’s

If you like the sporty/ trainer vibe, but want something cool and fun, choose these. You have so many options with colorways; keep ‘em more neutral or spice them up with something funky if you’re feeling confident.


Designer Kicks

You’re flexing. I get it. You’re on a date and you’re pulling out all the stops. Not my personal brand, but power to you. I’m more into sneaker culture than designer kicks, but some girl is going to dig the fact that you are sporting Gucci’s or Golden Goose, so if that’s your personal style, go for it. But don’t be mad if she assumes you’re going to pay the tab going forward forever. You made your bed.


Wear For Comfort:

Whether you travel every other day for work or fun, or you’re on your feet all day, you need a shoe that’s going to be comfortable.


Get the Wool Runners. Everyone is wearing them for a reason. You can’t go wrong. They’re comfortable, they’re washable, they slip on and off easily, and they’re only $95.

Allbirds Wool Runners/

Nike Vapormax

Get them in Plus, get them in Flyknit. Just get them. You’ll walk on springs. Wear them with confidence; if you can pull them off, buy them. They are the most comfortable kicks I own.

Vapormax Plus/

Wear to Impress Me:

Anything that was hard to cop. Any kicks that are currently trading online for more than you bought them for because you knew enough to buy them, will impress me. You scored the Travis Scott Jordan 1’s? I’m Impressed. We’re off to a good start.

Travis Scott Jordan 1 High/


You have style. Period. That’s what this tells me. You like classic designs, but you have an edge, and you’re probably not scared to take risks, and that always makes for an exciting person.


Y-3 Kusari II/


off white
Air Vapormax Off-White 2018/

Virgil holds a special place in my heart. I love most of his designs. So if you wear a pair of Off-White’s I will literally fall at your feet.

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