Why I Judge People By Their Sneakers (And You Probably Do Too)

Okay. Full disclosure here: I’m shoe guy. I’ve always been shoe guy.

Honestly, it’s sort of inevitable when you spend twenty-five years of your life professionally dressed in proper leather shoes. They’re just down there; you learn to look there first. But here’s the weird thing about getting older and noticing how casual the whole world has got: I’ve become just as judgmental about trainers as I ever was about button-ups and dress shoes at client meetings.

Margaret thinks I’ve lost my mind, incidentally. “Arthur, they’re shoes!” She says when I comment on someone’s choice of footwear. But she’s wrong.

Trainers are the most telling article of clothing the average person will wear.

Unlike suits, for example, where there’s a widely understood though not universally practiced template for what’s acceptable and what isn’t. With trainers, you’re totally blind, making decisions that speak volumes about who you are as a person without realising it. I discovered this whole world about fifteen years ago when I was old enough to know that there was some nuance to clothing besides simply dressing at an acceptable professional level.

I started paying attention not only to how my coworkers dressed for work, but how they presented themselves when we went out. Dinner with clients where everyone wears jeans and trainers. Firm retreats.

Weekend weddings. Things where the suit and tie comes off and you start to see who people actually are. That’s when I realised trainers could tell you more about someone’s personality than a suit ever could.

When you wear a navy suit with a white shirt, you literally blend into correctness. But when you wear one pair of trainers over another for a casual Friday meeting or weekend event, you’re consciously making a decision about what you want to say about yourself as a person. And everyone else picks up on that, whether they realise it or not.

Look at the partners in my firm. I have one – lets not name names, but he’s been here as long as I have – who wears nothing but perfectly white leather trainers whenever we’re all wearing jeans. Not designer high tops.

White trainers. Tennis shoes. And they’re always white, never scuffed, with a pair of dark jeans and a plain button-up shirt.

What does THAT say about him? That he embraces simplicity? That he cares about these things but isn’t trying to flex?

That he wants to look nice but not grab all the style points? Trust me, it’s high style. Contrast that to another partner in the firm who rocks shredded black converse chucks.

Black high tops, faded down to nothing. Completely different message. Don’t take yourself too seriously.

You were in a punk band in college. You secretly love making music playlists. You value authenticity over pedigree.

Completely different people reaching the same successful destination but presenting as night and day to everyone who meets them. I’ve actually watched opposing counsel do this during depositions. Comes in rocking some absurdly expensive white trainers – Maybe those barely-there leather trainers that some nonsense designer makes for nearly a grand – and proceeds to try to look like he doesn’t care that he just threw six hundred dollars down on shoes.

Almost pathetic, if anyone bothered to care enough to think about it. It took me a long time to think about trainers in that way. For the longest time I wore whatever random athletic trainers I had lying around when I wasn’t wearing dress shoes.

Older running shoes from way back when. Basic tennis shoes from the department store. Whatever wasn’t costly enough that I cared what they said about me because I didn’t realise they were sending a message at all.

Of course, once you start noticing that sort of thing you can’t unnotice it. You meet someone new at a restaurant and within seconds you’re not just evaluating their outfit, you’re analysing how they put their outfit together down to their choice of trainers. Everything else about this person becomes filtered through that lens.

The thing about trainers is they’ve got this thin line they have to tread between utility and fashion. Sure, they’re supposed to be athletic shoes you wear when working out or playing sports. But then why do most adults who wear trainers as casual footwear almost never USE them for their intended purpose?

Once you realise that, every trainer tells a story about who the wearer wants to project as a person. Do those guys wearing retro Jordans to the office remember Jordans from when they were actually revolutionary? Are they old enough to feel nostalgic for when basketball mattered more to society?

Do they think Nirvana was better than Kendrick Lamar? Yes, yes they do. Jordan retros to the office and you’re probably one of those guys.

See that woman wearing understated white trainers with no branding you can see? She read an article about capsule wardrobes and owns three of the same “different” coloured navy blazers. She’ll try to justify her trainers as versatile but can you really trust someone who owns that many navy blazers?

Also, she listens to podcasts about Danish furniture. Meanwhile, your gentleman wearing obviously expensive trainers wants you to know he reads fashion magazines and isn’t afraid to wear things you’ve been told are ugly. Seriously.

Look at those ridiculously oversized Bali sneaks that some French dude makes. People pay THOUSANDS of dollars for those clown shoes. What else are YOU hiding?

This whole thing is inherently goofy because, fun fact, trends change on a yearly basis. Case in point: a few years ago you would have worn outdoorsy trail runners into the city and instantly been labelled a gearhead who thought he could trade weekend warrior bragging rights at the office. Now everyone walks around Manhattan in hiking shoes they’ll never actually use to hike in.

The plain truth is I’ve fallen victim to this stereotype at times. Once tried wearing what I thought was a conspicuously minimal snebe to a casual partner dinner only to discover that “casual” had a different meaning for me and everyone else in the room. My sleek leather trainers were TOO much middle ground.

There are times when you just need to wear dress shoes or trainers, period. Your kids are sneaking up on you, too. Kids nowadays wear trainers brands I’ve never heard of to try to feel like they fit in with their friends.

It’s like they’re all having a conversation with their shoes that I’m not invited to.

Guys my age who wear trainers autumn into very obvious categories: They actually play sports, they’re pretending not to notice that we all dress casually now and getting burned by dress code emails or They MISS BEING YOUNGER THAN YOU. Margaret got me a pair of what she called “normal trainers” last year.

Basic white leather tennis shoes. Nothing fancy. “Wear these when we go out on weekends,” She said. “K.J. and the kids will come with us. Don’t overthink it.” Girlfriend was probably right.

There’s definitely a sense of sophistication to not caring what your shoes say about you. But I will say it again: I notice what you’re wearing down there. I know you think your shoes don’t send a message, but they do.

Whether you’re cutting off the trail runner trend at the knees or wearing rainbow glitter Adidas for no reason, I can tell what trainers say about you. I may be shallow, but I prefer to think I’m just observant. These days, when everyone dresses like they’re going hiking on weekends vs going to work, your trainers speak volumes.