Find The Sneakers For You In 2020

The best part about style in 2020 is that almost anything can look good right now.

Are you a dad? Do you wear jeans? Well people are literally paying extra to find pants that purposefully fit the way yours do on accident.

Do you want to constantly dress like you’re ready to binge Breaking Bad in bed and only wear sweats and XXL t-shirts? Kanye is there to tell you it’s safe to be comfy.

Or–my personal favorite–do you want to embrace your inner cowboy? There’s a place for that, too.

The worst part about getting dressed in 2020? Well, it’s that almost anything can look good right now. The 90s, the Yeehaw Agenda, boxy looks, endless texture options, oversized fits, normcore, tassels, and chunky sneakers. How do we make sense of all of this? How do we wake up in the morning and get dressed when almost anything I wear could look good… or I could just barely miss the mark enough to look completely ridiculous.

You can dress like Jerry Seinfeld and end up in a GQ article, or end up with multiple people impulsively asking you if they should mow their lawn using the “striping” or “overlapping” technique.

Regardless of your look (or desired look), there’s a place for you (yes, even the new you) in 2020. Still, that can feel a bit daunting. Some people want dabble in new trends, but resist looking like they emerged from the Urban Outfitter’s version of Steve Urkel’s Transformation Chamber. Others want to follow fashion to its darkest abyss and see what’s on the other side. And then there are some who just want to find a style identity that will remain timeless regardless of what Timothée Chalamet wears at the next red carpet event.

Whatever you use to guide your style decisions, sneakers are likely part of your wardrobe, and if they aren’t, they should be.

Tennies, kicks, sneaks… call em what you want, but they can add another level of complexity to all of this. They are an entire industry unto themselves now, and they offer enough variety and price points to keep your head spinning in an already unsure time. And while I can’t help with the bigger picture questions about wearing clothes in the new decade, I can tell you which pair of sneakers makes sense for you, no matter how you’ve chosen to dress.

FOR THE UNDERSTATED

A white leather sneaker is the Spider-man movie of shoes. People keep making new versions of them, and I’m not positive they’re getting any better, but that should never stop us from consuming them.

These sneakers are some of the most versatile shoes you can own, they’ll go with almost anything you wear (as Anna has shown time and time again), and they won’t break the bank.

Adidas’ Stan Smith’s are the Toby McGuire of this category–a classic that will always be worth going back to (I ride with Toby). I’ve had multiple pairs through the years, and while I don’t own any now, I know I’ll go back to them one day.

Anna owns the Nike Court Royale (you can find the women’s sizes here), which I will refer to as the Andrew Garfield of the group. They’re a slightly lower price point, but give you the same look and comfort as the Stan’s.

Either of these options will give you a sharp and classic look, but can also blend into any street style or athleisure vibe you throw at them.

Who’s the Tom Holland of the group, you ask? None other than New Republic’s “Kurt” leather sneaker. I just got these a few months ago, and while New Republic’s sneaker is definitely the new kid on the block, it also might be the best. Why? Because it’s not trying too hard (looking at you, Toby, in Spider-man 3), there are no flashy labels to distract from its clean design, and the premium materials and pointed toe makes this one stand out ever so slightly from its predecessors.

Listen, I’m a Spider-man stan, so I’m here for all of it, and while I wasn’t always the biggest fan of the plain white sneakers, the versatility is unmistakeable. If you don’t have some white leather sneakers in your closet, change that.

PS: If want a little more “it” from your white sneakers, go with some classics from Reebok. I got these for Anna in the fall, and they were a huge staple for her during fall.

FOR THE ATHLETE…OR THE PERSON WHO WANTS TO DRESS LIKE ONE

Athleisure has made looking like you’re going to the gym (but not actually going) as popular as ever, and I’m here for it.

Early last year I tried a pair of Nike Vapormax 2019‘s on for the first time, and I was shocked how much I liked them. They are kind of a strange shoe at first glance, but they’re extremely comfortable, water resistant (seriously), and far more versatile than I expected.

They’re performance ready for workout warriors, and they can go with everything from casual work clothes to chic vibes and street style. This pair of tennies truly took me by surprise, and I wear them all the time.

I went for the “Ghost Black” colorway, because I wanted to make them as versatile as possible.

FOR THOSE DIPPING THEIR TOES IN THE “CHUNKY SNEAKER” WATERS

If you’re looking for a “dad” shoe, it’s hard to know where to start. It’s sort of like wanting to try calamari for the first time. Do I really want to spend $24 on an appetizer that I might not love? I get it. Dad shoes are the kind of shoe that someone looks at and goes “Oh… those look… comfortable.”

THEY ARE, KAREN.

And, if you want to take a leap, why not go with a timeless classic that doesn’t venture too far off the athleisure path? The Air Max 95 will never, not be cool, and that they have a chunkier silhouette only makes them that much more popular in this day and age. Anna purchased a pair last year, and it’s been a go to for her in athleisure and streetwear looks ever since — including one of our favorite shoots from 2019.

FOR THOSE WHO WANT TO BE UN-BASIC (AND ENVIRONMENTALLY FRIENDLY)

The Everlane Tread (you can find women’s sizes here) is the shoe that took me by surprise in 2019 more than any other sneaker.

Not only do they have a clean but bold look, but the Treads basically have zero break-in time. I took them straight out of the box and then went for a 3 mile walk, and I had no complaints about the comfort. Very few sneakers are as well balanced as this shoe: simple but not boring, stylish but not flashy, and high quality, but not overpriced.

For what it’s worth, they also have virtually zero carbon footprint due to the way Treads are manufactured and the insane amount of recycled materials used. Sustainability is a marketing tactic in a lot of cases, but Everlane has really invested in the process here. You won’t necessarily find me protesting at City Hall, but being a good thing for the environment is never a bad thing.

I went with the “Off White; Gum Sole” colorway.

FOR THOSE LOOKING FOR THE HYPE AND “HEAD NODS” IN 2020

If you really just want to plunge headlong into the “hypebeast” sneaker game, there is only one pair of shoes in one colorway that I can truly recommend, and trust me, I’ve tried enough to know…

I’ve given the Yeezy 500’s a shot, and they were comfortable, but eventually it wasn’t my style anymore. The Yeezy 700 Waverunner is the chunky dad shoe that started it all, and while I love the colorway and “modern classic” that is this sneaker, it can be hard to pull-off in every day life. And I’ve even had a pair of the all-time greatest, the true classic, Air Jordan 1s. But again, as I started to phase out classic “streetwear” essentials, these became harder to pair with my clothes.

All of those sneakers are great, and they’ll even get you the head-nods you secretly crave, and they may even end up as the conversation starter you didn’t know you needed. But, to me, if you’re looking for a sneaker that pairs “Hype” with versatility (something I look for in every high-dollar purchase I make), then look no further than the Yeezy 350, Sesame.

The Yeezy 350 is an instantly recognizable silhouette, and this colorway is the sort of “grown-up” look these sneakers need to not make you feel like you’re chasing the same style as my 10 year old nephew.

If you can’t figure out what to wear in 2020, I can sincerely relate. But I hope this guide at least gives you the encouragement you need to find a steady and versatile pair of sneakers to start the new decade.

SIZING

Adidas Stan Smith: True to Size
Nike Court Royale: True to Size
New Republic “Kurt”: True to Size
Nike Vapormax 2019: True to Size
Air Max 95: True to Size (Purchase .5 size up if you have wider feet)
Everlane Tread: Purchase .5 Size or even Full Size up if you have wider feet
Reebok Club C: True to Size
Yeezy 350 V2 Sesame: Purchase .5 Size Up; Full Size up if you have wider feet