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I grew up in a big family.

Like 1 of 8 kids kind of big.

Buying “new” was never an option. If I wanted clothes, I’d skim the racks of Goodwill or wait for hand-me-downs. And since I was the seventh of eight, the probability of getting something, anything, in decent shape by the time it got to me was painfully low.

As a product of the 90s, a lot has changed in the last 25 years, especially where men’s clothing is concerned. We’re witnessing another renaissance period in menswear; let’s call it the Drip Enlightenment. Where clothing once represented functionality, what you wear now is a signal for the tribe you belong to. Your drip is about self-expression, and it’s shifting the way that guys consume and shop.

How?

The rise of re-commerce (The RealReal) and clothing rentals (Rent The Runway, IPO’ing soon) are worthy examples in womenswear, as is Depop (who recently was just acquired by Etsy for $1.65 Billion). None of this is accidental; it’s a reflection of the times. 

But on the men’s side, the thought of dudes renting clothing (not named a tuxedo) sounds crazy, until it's not.

And in 2021, it’s not so crazy after all, thanks to a few bold startups hell-bent on shifting the shopping paradigm for men: welcome, Seasons and KYX.

The timing around having the freedom to rent your clothing feels apt, but before we look at why that is, let’s first unpack how we arrived here.

Let me jog your memory.

When clothing was a function

Up until the last 50 years or so, men’s clothing was sold mainly as functionality. Whether you wore a blue-collar or a white one, clothes were made for the job you worked.

You had a daily fit. But it never changed. 

During the 1970s in the west, though, things changed. A younger generation catalyzed that change with their political views and a sex, drugs, and rock n’ roll lifestyle. The outcome created a stronger sense of self and individuality for Americans. In the aftermath, brands like Stüssy rose to influence in the 80s and 90s.

And then the internet happened, which paved the way for two crucial cultural shifts to unfold.

1 // Blogs like A Continuous Lean and Tumblr accounts like FuckYeah Menswear further democratized style advice for guys in the late 2000s / early 2010s, creating nuance that didn’t previously exist. The medium shifted again in the mid-2010s with the rise of Instagram and influencers.

2 // The NBA enforced a player dress code enacted by the late David Stern. People criticized the decision for being rigid and racially biased against black athletes, but it gave way to a style renaissance that now feeds into the hype cycle we know within streetwear and sneaker culture. Players like Russell Westbrook were early champions of this movement.

The rise of subscription boxes

First came online shops, then the subscription companies followed, which was the first sign of menswear offering rental-esque models. Startups like Trunk Club (TC) and Stitch Fix (SF) emerged in the early 2010s. And while they were revolutionary for their time, their narrative was to help guys dress better by giving them the training wheels (i.e. a stylist who dressed you).

The idea is that you, the customer, are a novice. You need someone to help you get dressed.

So, stylists took control, curating boxes of clothing from brands like Billy Reid, Under Armour Faherty, and so on, allowing dudes to keep what they liked and return what they didn’t. TC had “clubhouses” (physical locations) with salaried stylists who made bonuses off keeping a book recurring “clients,” while Stitch Fix focused on creating algorithms based around Style Quizzes that new customers completed.

Ultimately, TC was acquired by Nordstrom and closed all physical locations, focusing on digital-first, where Stitch-Fix has chugged on, reporting over $530 million in revenue (men's and women's during Q3 last year alone.

But we’re in the Drip Englightenment, for God’s sake. Guys are more willing and confident than ever to wear what they want, how they want. And knowing that creates opportunities, one of which is ready for disruption: rentals.

The modern playbook: access > ownership

If RTR has proven one thing, it’s that access beats ownership. Having beautiful things when you need them is better than having them when you don’t need them. Hello, weddings, meetings, parties, events?

This is where Seasons is carving its niche as a rental platform for men. They carry luxury-level designer clothing like Dior, Gucci, and Acne Studios, and it’s working. A few months back, Regy Perlera, co-founder and CEO of Seasons, tweeted that the brand is averaging $56,000 in monthly recurring revenue and just crossed over 600 active users.

“Fashion (especially menswear) has evolved so quickly the last few years,” says Perlera. “Right now, rental, at its core, is a much easier barrier to entry than buying something online, especially at a luxury price point.”

Everyone’s learned to adapt after being stuck at home the last 18 months, from working remotely to living on the road. So, the thought of thinking about where you're going to live, let alone what you should wear to dinner, is a daunting prospect for many. So consumers want to experiment, and Perlera intends to be there for them when they do:

“The internet has proven that there’s an impermanence to everything. When it comes to clothing, we don’t need to own much because we move on so quickly, so we’re building a platform to enable that philosophy.”

The same goes for KYX, a sneaker rental company that’s making waves on the internet since it launched in June. While the words sneaker and rental don’t intuitively go together, Leland Grossman, the Marketing Director, explains that the market is ready for it. The company has around 1200 active members already.

“The sneaker industry has exploded over the past few years,” he says. “But as more people have become interested in these shoes, the supply has not increased in a way that’s beneficial for everyone. The problem we’re solving is access.”

Ah, access.

Having access is a challenge for many sneakerheads and enthusiasts alike, who repeatedly take “L’s” on Nike’s famous SNKRS app. When there are only limited quantities, sizes, and styles available, those who land a pair of kicks will resell them on platforms like StockX and GOAT, further driving prices to obscene numbers.

Try before you buy

Perhaps the most exciting prospect in all of this is “try before you buy,” where both brands are having success. Rather than forcing yourself to buy something you might not want in 6 months, both companies give you the ability to make low-risk decisions by “testing the waters” first.

Grossman thinks this is a perfect way for customers to decide whether they like a pair of sneakers: “Sure, maybe you like the way a new release looks,” he says, “But at $500+ on the resale market, is it worth taking the risk on? We remove that risk giving you the freedom to try them before committing, and if you do like them, you can purchase them at a discount through us.

The challenges with renting

First off, there are obvious hesitations around wearing used sneakers, which some find downright repulsive. Grossman and KYX have it covered, though. “Have you ever been bowling before?” he asks.

“Images of a sweaty teenager spraying shoes that have been worn hundreds of times, and somehow we accept that but question this? We get it, which is why we ensure all shoes are cleaned, sterilized, and brought to a like-new condition when we receive them… If the shoe doesn’t look, feel, and smell like it’s new, we’re not shipping them to you!”

Mike Sykes, the host of USA Today's 'For the Win' sneaker show and founder of Kicks You Wear, also unpacks another obstacle KYX could face: buy-in.

“The biggest challenge for sneaker rental companies, in my eyes, will be about getting the right people to buy-in. As sneakerheads, we tend to get stuck in our ways, but we’re also the ones who determine what is cool in an organic way. Getting sneakerhead buy-in or approval will be essential for any company looking to rent out sneakers. That takes time.”

For Seasons, striking the right formula for their brands and customers is an ongoing journey too. “There’s a delicate balance between inventory and membership. To grow, we need the availability of merchandise and merchandise people are interested in renting” says Perlera. Though, as the company gathers better data on its customers, those fears should subside.

Where are we going?

By 2023, more than 25% of your wardrobe could consist of pre-owned pieces (according to Boston Consulting Group and Vestiaire Collective).

What we see with Seasons and KYX is no accident. It’s what the people want, and this is just the beginning. The future of retail and eCommerce is shifting before our eyes, in a good way.

As both startups grow, I expect we may see the following unfold in the rental space next. Here are a few of my predictions:

• Grailed and Depop will enable vintage rentals on their platform, take a seller fee, or charge a subscription for premium access for exclusive vintage goods.
• Hodinkee further expands its timepiece empire, creating a watch rental marketplace where customers can opt into a subscription-based program.
• Individual brands will create seasonal pieces expressly set aside for renting out to customers.

Consumerism has conditioned those in the west to believe that more is better. But I don’t see it that way. After living through the worst parts of a pandemic, committing to anything is so 2019. It forced many to rethink why one has to own so much stuff. Don’t get it twisted; I’ll always invest in the best. It’s essential to have those moments where you buy something special for yourself, something unique. Still, I’m a firm believer in owning fewer quality things, and platforms like Seasons and KYX are finally allowing consumers to do that.