Fashion, Object, And Wit With Ashley Cheeks Of The Drive New York



"Most of the designers I carry in the shop I also consider friends," Ashley Cheeks of The Drive New York expressed in response to one of our interview questions, "Coming from a design background and knowing how much work goes into making every piece from the first sample to production makes me really appreciate and value their work."

Ashley's knowledge of the fashion industry runs the gamut from design to curation and because of this, she has a unique understanding of what goes into truly building a successful brand. Having first started out as a fashion designer, Ashley eventually found herself interested in fashion buying and since then, The Drive has evolved into a respected space for contemporary designers to be discovered. In that same vein, we were excited to find that the platform's designer community features coveted brands we work with here at Brand Assembly which include Rachel AntonoffSamantha Pleet, and Carleen. These shared values and Ashley's penchant for contemporary fashion inspired us. We found ourselves wanting to know more about her plans for The Drive, her thoughts on the contemporary market, and what she's assembling daily. Check out our full conversation with Ashley below, and visit The Style Line for an exclusive second part of this story. 

Please introduce yourself!

My name is Ashley Cheeks, and I’m originally from the south, but I’ve lived in Williamsburg with my husband and our two cats for almost 10 years. I am a fashion designer turned shop owner, who in real life is kinda shy! Those who know me might say I get way too silly and they would definitely say I can’t sit still. I have a slight obsession with creating mood boards and enjoy getting lost in the process. Also, going to see the American Ballet Theater at the MET is one of my favorite things in life. My best friend, Odiri, is an ABT Young Members patron (which means I'm often his special guest)! I am really lucky to see my favorite dancers perform several times a year. I always say my favorite season is ballet season!  


Talk to us about The Drive’s focus on “fashion, object, and wit” - how would you define each of those ideas?

For me “fashion, object, and wit” is our quick little slogan for what the site contains. We are a fashion driven website that also sells objects. I added “wit” because the designers we carry are very smart and clever.

How would you describe your relationship to the designers you work with and carry? 

Most of the designers I carry in the shop I also consider friends. Coming from a design background and knowing how much work goes into making every piece from the first sample to production makes me really appreciate and value their work. My goal is to travel and visit all of the designers we carry and really build on the relationships we've created thus far. Seeing them in their own environment would be really inspiring to me. 


The Drive also has a namesake label, tell us about it! Do you ever find it difficult switching from curator and buyer to designer and vice-versa? Can you offer any advice to emerging designers who may be looking to venture into a similar space? 

I’m actually coming from the opposite direction! I started off as a fashion designer, took a break and then sort of wandered into the buying process. My advice is to start small and start where you are. Find people who will work with you in small runs whether it's creating your own clothing line or making your first opening buy. You can always buy more later.

What are your thoughts on the contemporary market and what excites you the most about this specific group of designers?

I love the contemporary market because it borders the line of wearability, creativity, and luxury. Designers in this market have an actual point of view and a story they are telling. They care about the materials they use, where it’s being made, and who is buying it. The inspiration behind each collection is my favorite part about market week.


Describe your ideal drive…

My ideal drive would either be on the big island in Hawaii or on the coast of Italy, with the windows down and my husband driving. We would be listening to some roots reggae, I’d be wearing an Ajaie Alaie skirt, a loose cut off white tee, my Nandi Naya Yoli hoops, and no shoes with my legs folded totally chillin’. I would be thinking about how beautiful the world is, smelling the coastal air, feeling the sun on my skin, and we would be talking about future goals and of course any cute animals we saw along the drive.

What do you assemble daily?

Lists! I love to make a list so I can check things off. I even add things to the list I’ve already done for the day so I feel more productive! I also have a library of ridiculous animal images that I’ve been building for years… cute animals never get old!