You might not immediately know Sean Conway, but he's been in the game forever. A true OG—one of the original KITH employees and now at Dover Street Market New York—Sean has been collecting footwear and streetwear before it was cool. Never one to really dabble in the resell game, Sean's now at the point where age and the ever-expanding need for space in the city dictate a change. Luckily for us that means an open archive filled with decades worth of the most covetable sneakers and sportswear. Get to know Sean below in an in-depth interview that explores everything from his collecting roots to how street culture has shifted dramatically over the past few years, and then shop all three drops—with lowered prices throughout—from his unmatched collection.

Okay, for starters, for those not familiar, can you please tell us a little about yourself and what you do.

So I'm a 30-year-old regular guy from Annapolis, Maryland. Grew up in a preppy sailing town, went to catholic school, lived that normal suburban life. Went to Washington college on a lacrosse scholarship, quit after 2 months, smoked a lot of weed, partied with friends, and had a good time. Got two bachelor degrees out of it though, and graduated Cum Laude in 2008. Definitely made some mistakes during those years, but you can't learn how to make yourself a better individual unless you make mistakes.

Ever since the 5th grade, I've been into shoes. The Jordan Jumpman Pro Strong Vin Baker edition was the first pair I remember balling in. Then, I grabbed the OG Dunk goldenrods, some old es' Kostons, Gary Paytons, Laney's, and rocked the Kevin Garnett gold Flightposites in 8th grade. Getting my parents to spend $210 on some sneakers was a hard bargain. But my parents are amazing. They always looked out for me, whether they had the money or not. I couldn't be more proud of where I come from and how I was raised.

As a teenager, I started working at a local skate shop and fell in love with Nike SBs. I had a lot of good ones back then. The first pair I bought were the Shark Dunk lows from the OG series. From then on, I was a collector of mostly Jordans and SBs. During my college years, I kinda fell out of collecting, but once I moved to San Diego, I got back into it pretty quickly. I remember copping Skunk Dunk hi's from Blades, Parra Air Max 1s on sale from The Attic, finding 2001 Bred 1s on Craigslist for $40. It was a great time to be a collector. That was from 2008-2010.

I moved back to MD in 2010 and continued collecting, buying and selling at conventions every now and then, back when it was $100 for a table at Sneakercon and Dunkexchange. I mostly just bought for myself though. If there was stuff I didn't use, I sold it. But I always kept at least 300-400 pairs in my collection. It's when it got close to 1,000 that I had to let some things go.

In 2012, I moved to NYC. I had made some connections and started working at Kith. I was one of the first 11 employees that worked there. It was a small, tight knit group of friends, just learning each day, and always taking care of each other. It was an amazing time in my life, although I bought way too much while working there. After almost 4 years, it was time for me to move on, and even though it was super hard for me, I left Kith and now work at Dover Street Market. I’m still buying too much, but trying to get rid of the crazy amount of unused stuff I've bought over all these years.

How big would you estimate your collection is as of today?

Today, my shoe collection is around 500 pairs, and even more pieces of clothing.

Why offload a bunch of your collection now? What are your primary motivations in sharing it?

Honestly, I just have too much stuff. It can be overwhelming at times. Living in NYC, there's not a lot of space to store your stuff. So, between my parents' house in Maryland, my spare bedroom, and my two storage units, there is just too much stuff that I don't even get to wear, stuff that I forget I even owned. It's truly a matter of saving money and space. I will never stop buying, I'm addicted. But it's a combination of me getting older, my style constantly evolving, and the the way things have changed in this culture I've loved for decades.

I will always be buying sneakers. I've bought around 8-10 pairs this past month, so it's not like my passion for sneakers has dissipated and become a part of my past. It will always be a part of who I am.

I also want my stuff to go to the right people, people who care about each item and can relate to why each piece is so special. That's why I think that linking with Grailed is such a great idea. I'm able to reach out to a select group of individuals who have similar taste in sneakers and fashion. They've had a great home for the time that I've owned each piece, so I would like that to continue on with each new owner.

It's interesting how you think both your personal style and the culture have evolved over time. Do you think those two things go hand-in-hand? And what is your opinion on the status of sneaker culture, collecting and streetwear in general as someone who's been living it for most of your life?

As you grow older, I feel like your style is constantly changing. So yes, they almost do go hand-in-hand. These days, you'll find something great, it ends getting hyped up too much, and then it's moving onto the next thing. Today, my style stays somewhat consistent, as it's always been streetwear/skate based, but as I've gotten older, I've found ways to blend different types of fashion, and make it my own style. I can wear vintage Polo with some Junya one day, and then wear Supreme and Casey Casey the next. I just wear what I have, and try to best to tell a story of my style evolution through the way I dress every day. It definitely started out more skate inspired, wearing tons of Stussy, Freshjive, and some early Huf and Diamond Supply. Then things got a little more preppy during college with button-ups, polos, khaki shorts, denim and sandals. After college, I loved to San Diego around 2008 which is where I found my love for vintage. Hitting flea markets every weak, and just continuing to collect.

Moving to NYC in 2012 gave me access to way more fashion and feeling inspired daily when walking the streets—meeting new people, connecting, networking, and, most importantly, just learning about the world of fashion.

The current status of the sneaker culture is something that honestly confuses me. On the one hand, there are still the OG's, the guys that have been doing this for decades, still out here waiting in lines, but then it's hard because this new generation seems to be way more aggressive, almost greedy in a way you could say. To most people out there waiting for shoes/clothing to release, it's more about the value of the item than the item itself. They aren't out there because they want something they plan on wearing. They are out there because they want to make money. And I won't lie, at one point in my 20's, I did some buying and selling, though not even close to the extent that these guys do today. But it was fun back then. For me, it was always about collecting, as you can see from the things I’m releasing through Grailed, these are pieces that I bought to keep, to collect, and to eventually wear. It’s just gotten to be too much for me to handle.

What things—for example, trends or brands or designers—have you feeling optimistic about the culture and where it's currently headed?

When I started collecting, trends were very different, style was very different, culture was very different. The sneaker industry has grown exponentially since the glory days of Nike SB, which was when I started seriously collecting. They were collaborating with great artists, and distribution was on a much smaller scale. You had to have a top tier account with Nike, and you had to have been a retailer selling Nike product for at least two years before you could even get the good releases, which were known as Quickstrikes back then. It was more collectible back then. Now that Nike realizes their potential sales for certain styles or collaborations, they produce them in the hundreds of thousands, because they know it will sell out. The re-sell market has a lot to do with this—guys out there buying anywhere from 10 to 100 pairs of a particular model to try and make a profit. And it works for both parties most of the time.

When I started, it was SBs and Jordans, along with some random Dunks and Foamposites here and there. It was around 2010/2011 that things shifted and people were getting more into vintage running models and slimmer/more fitting silhouettes. Asics and New Balance started making a big comeback, Nike followed, started releasing more Air Max models, and developed the Flyknit and Lunar technologies, which only put them further ahead in an industry they've dominated for decades. These days, I feel like that trend is fading. People are going more towards '90s streetwear looks. It used to be skinny, cuffed APC jeans, long, fitted tee and a pair of runners. Now, it's some Dickies pants, a vintage rock tee, and a pair of Vans or Converse. I feel like this new trend won't last very long though either. Even Demna Gvasalia has said he doesn't see it lasting. I feel like everything’s moving more towards high-end fashion and luxury goods, and even though footwear is always a very important part of your look, I don't see sneakers being as collectible as they once were due to how accessible everything is now. There will always be special releases that people will want, and I don't know if it's me gettting older, or the way things have changed, but I don't have the time/patience to put in the effort I once did when 100 dudes are all yelling at each other outside a store to get something that doesn't seem as special as it once did for me. Thankfully, if I really want something now, it's not super hard for me to get it. I've met a lot of good people throughout the years and it's those friendships and bonds that have gotten me to where I am today.

With so much noise out there in the market, so to speak, where do you think a kid should start if he's just getting into the streetwear and sneaker game?

My motto is, and always has been, BUY WHAT YOU LIKE! Don't be a follower, be an individual. Maybe find something that other people aren't into, or find something that really speaks to you, and go with it. Your style will continuously evolve, but when starting out, always buy what you like. As for sneakers, try starting with general release that aren't super hard to obtain and work your way up from there. It's not easy to just jump in and grab all the hyped sneakers that are releasing. Don’t go crazy over what other people think, be yourself, buy what you like, and be patient. Good things always come to good people.

You touched on this a bit earlier, but what do you think about Grailed and the community surrounding it?

I think Grailed is a great platform for buyers and sellers to discover/sell product that can't be found in stores anymore. It is great that it appeals to a certain demographic, one that's more interested in fashion and footwear, rather than appealing to everyone. Grailed has great product that is not easy to find, and they are the 3rd party that connects the dots, making sure the product gets into the right hands. It puts the right people in touch with each other. And it's cheaper than eBay, so what more can you ask for?

Finally, of everything that you're currently selling, what item or items are the hardest to let go of?

Definitely the Nike Air Yeezy 2. It is one of the most iconic models of our generation, the last model Kanye made with Nike, and it's the better of the 2 models they did together. Also, the Jordan 9 Bin Premio 23's. They were probably the hardest shoe for me to obtain, but as much as I love those shoes, they’re too big, and it's time to let go of some stuff. The older Supreme stuff too, but I was heavier when I bought a lot of it, and I can't fit most of the stuff I'm selling anymore. It's hard to let go of anything really, but when you have so much stuff, sometimes it gets lost in the mix. Again, I’m just happy to have more space.