How To Wear Sneakers On A Date

Valentine’s Day is coming up, and it’ll be here before you know it. And while you are probably keeping an eye on Valentine’s Day because of sneaker drops, you are also probably keeping an eye on it if you are in any kind of romantic relationship.

I personally believe that there are very very few instances where you can’t get away with rocking sneakers, and a date is not one of those instances. You should absolutely go on dates in your sneakers, and to give you a little bit of help and guidance well early enough before the (arguably) special day, I’ve come up with a list of tips and tricks to help you look, feel, and rock your best.

These tips are more helpful for dates and special occasions with a considerable amount of gravitas (e.g. first dates, date nights, anniversaries, etc), but they are great subtle touches to casual engagements as well. Jerry Rice isn’t the GOAT because he only did the minimum.

Make Sure Your Sneakers Are Clean.

Some of y’all don’t put on a decent clean pair of sneakers on when you’re with a special someone and it shows. I wouldn’t ever imagine in a million years going on a date with someone wearing sneakers that look like I did yardwork in them unless I didn’t like the person. And you don’t even need to be a sneakerhead for this tip; this is just a general principle of personal appearance. If you’re going to have a decent outfit that was planned/prepared, then it only makes sense that you have decent sneakers as well. Don’t leave part of the job undone.

Know Your Agenda.

Well, you should know what’s going to happen on a date anyway, but this is also important for your sneakers because depending on where you go and what you will be doing, you can have a clearer picture of what kind of sneakers will be safe for the occasion. A little scouting never hurt anyone. Get an idea of what you will be doing, where you will be going, and then strategize on some options.

Choose Sneakers Based Around Your Outfit, Not The Other Way Around.

Most sneakerheads will make the quip about picking out their sneakers before their clothes. I know I have done it my fair share of times, you probably will too if you already haven’t. But, I contend that it is better to choose your sneakers for the occasion following the clothes because if you have any shred of fashion/style sense, then it forces you to wear your sneakers that are coordinated with or compliment your outfit.

And that’s another thing. I know you probably have the urge to bring out your grails or your special sneakers on a special occasion. I have absolutely no beef with that. But, if you can help it, try to refrain from wearing those grails that are more “out there”. You know what I mean, and what it means for your respective rotation.

Err On The Side Of Comfort.

I don’t know about you, but a lot of times dates tend to just fly by and what was supposed to be 1-2 hours ended up being 6. Pick a sneaker that’s not going to have your heels aching after extended periods of wear. Some good ideas to think about are React or Boost sneakers. Even if you don’t have any sneakers that come with React, Boost, or similar technologies, there is probably still a good chance that you have sneakers in your rotation with some sort of adequate cushioning and support. If not, these might help.

Try To Wear Sneakers You Don’t Have To Worry About.

This doesn’t necessarily mean wear beaters, although I often do advocate for beaters over grails on a night out. But on a date night out, you want to impress the other person. That’s logical and makes sense, again, no beef from me. But, in a case like this, I would find a middle ground (or sneakers): Not a grail, but not quite a beater. Not too sensitive of a sneaker when it comes to fabric and material, but also not your basic rubber and pleather. Finding that balance on a date sneaker is probably the most clutch thing you can do in this instance because you get the style, with the fact that should something happen to your sneakers, the situation can be better helped than with a more delicate sneaker.

One case in point, and this one is free: the Air Jordan XI is a sneaker that fits this bill. Why? Because although it is a great sneaker and one of high renown and history and meaning and all that, but, a scuff, mark, dirt whatever can ridiculously easily by cleaned off. The fabrics and materials on that sneaker are easy to clean and don’t take a lot of effort for a good scrub. I wore the Concords on a date once, and halfway through it, it started raining outside, when it was perfectly fine and dry just prior. I had to walk in the rain some, step in some light concentrated areas of water I wouldn’t count as puddles, and as a result, may have been some rain dirt on the soles and the leather was watermarked. But all I had to do was a basic clean of them, and I was good to go for the next time around.

Don’t Look Down At Your Sneakers All The Time.

As sneakerheads, we are wont to do this. All the time, but it’s important to remember that this time around, you’re on a date. Eyes on your date. And on the appropriate places.

This isn’t just a sneaker thing, this applies for a phone, a tv at the venue, etc. Don’t distract yourself or let yourself get distracted from your date and the nice time you two can have.

Try Not To Look Like A Sneakerhead.

But Jordan, didn’t you write a piece about

Yes, I did. And while I do still believe that there is no one way to look like a sneakerhead, there is still that stigma and set of fashion stereotypes about the culture. You know what they are, don’t fall in to them on a date. Please dress decent, not looking like you just finished your shift at the consignment store. If you don’t know what to wear on a date, Google what to wear on a date. It’s likely your favorite fashion/style publication will tell you how to do this. In fact, they probably have a version that comes out at least once a year.

And in conjunction with the point of picking your clothes first then sneakers, don’t try to game the system wearing clothes that make your sneakers the focal point of your outfit. You can go one instance without the alphet being all about the sneaks.

These are just a handful of things you can and should do for your sneakers on a date, but this is not a definitive, exhaustive, list. If you have any great tips for rocking sneakers on a date, get in touch, and I’ll update this page. Have fun on Valentine’s Day!

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