The authentic and timeless world of Ralph Lauren
Spring 2026
RL/People

THE RL Q&A: Jake Woolf

The veteran menswear writer and content creator knows how to put his own spin on the classics—especially when it comes to his collection of vintage Polo.
If you’re a fan of modern-day menswear, the odds are good that you know Jake Woolf. Maybe you’re one of the hundreds of thousands of followers of his classically cool style on Instagram and TikTok. Or a reader of his breezy style musings and market coverage on Substack. Or perhaps you know him from his former work as a staff writer for heavyweight publications like Hypebeast and GQ. Growing up in Connecticut, he was more interested in the roll of a button-down collar than the basketball jerseys favored by his classmates and spent his free time absorbing as much inspiration as he could from movies and magazines. Today, the 34-year-old writer, editor, and content creator has come full circle, using his stature in the world of menswear to teach a new generation of guys how to find their personal style. “I think about clothes and style all day, every day,” Jake says. “So I’m grateful to have a platform where I can share it with a new generation, because I remember what it was like to be new to all this and not know where to start.” Now based in the Upper East Side of New York, just a few blocks down from Ralph Lauren’s Madison Avenue flagship, Jake took us around his neighborhood while wearing some of his go-to vintage Polo pieces.

Were you always into clothing? What got you hooked?

I was always into the idea of how I looked. Even when I would play sports when I was young, I cared about what sneakers I was wearing just as much as how I was performing on the court or on the field. And in high school, I was always thinking about what I wanted to wear, which was right around the time that I discovered menswear magazines and internet blogs that gave me a real education on the history of clothing.

Where were you getting your style inspiration when you were growing up? What were you reading and watching, back then?

I definitely had a Rebel Without a Cause obsession for a time. James Dean’s outfit in that movie was like a menswear blueprint for me: white T-shirt, blue jeans, black shoes, and a Harrington jacket. The Great Escape with Steve McQueen was another. I saw how these characters were wearing basic pieces like a sweatshirt and a leather jacket and khaki pants, and I thought, ‘How can I look like that today? What makes these outfits feel so timeless?’ I was reading GQ, of course, along with some more streetwear-leaning magazines and blogs. That was a key part of my early menswear education. I realized there are people out there who not only care about clothes the same way I did but who had a huge depth of knowledge about them, and their job was to share that with other people.

How did you turn your interest in menswear into a career?

After my freshman year of college at Temple University in Philadelphia, I got an internship for a small menswear brand in New York. The first couple weeks I was working there, I got to go to Paris for a trade show, met Pharrell Williams at a party, and just got immersed into the world right away, seeing the back end of how the industry works. I was in a film program at the time, but as soon as I got back, I transferred to Parsons School of Design in New York. That experience made me realize that it really was possible, that I could take something I was really passionate about, and do something with it, career-wise. So I applied to a job at Hypebeast and became a writer, working around my classes. I wasn’t making a lot of money, but I was making connections and got to meet so many people who I had only ever read about—designers, editors, musicians, everyone. It all built very naturally from there.

You’ve covered a lot of ground in your writing career, and in content creation. What do you like to focus on now in your work?

I see the content that I create as, first and foremost, educational. I’m very passionate about great design and that’s what I love to talk about, whether in videos on Instagram or written stories. I want to share my knowledge. Let them know what makes a certain pair of chinos the absolute best, and what details make them so wearable and comfortable and good-looking. Or, everything that goes into making a great pair of shoes, from the materials to the craftsmanship, the provenance and the design details to the comfort level. I love going really deep into that special alchemy of great things, and what makes certain products truly special.

How did you get hooked on collecting vintage?

When I was first getting into menswear, I was reading about the history of denim jeans, and Army chinos, and oxford cloth button-downs. As I was learning about what the original sources were for all these iconic garments that were a part of my wardrobe, I wanted to try the originals—which meant vintage shopping. There’s something cool about having the very first version of a piece that became the foundation of an entire industry of clothing. And how a garment that was first created in, say, the 1950s survived, rather than ending up in a landfill somewhere, to have a new life today.

What does your Ralph Lauren vintage collection look like these days? Do you have any favorite pieces?

I probably have about 25 to 30 vintage Ralph things right now. I recently picked up a P-Wing crewneck sweatshirt, which is a cool flex to have in the collection. It’s one of those marquee vintage Ralph Lauren products that I think you just have to have, as a collector. As for favorites, it’d have to be my Polo chinos from the ’80s. Made in the USA, pleated, Big Fit with a slight tapered leg. They emulate that Americana prep essence and are perfectly dialed into everything that Ralph stands for. When he made them 40-odd years ago, these Big Fit chinos were new, cool, exciting products. Now, decades later, they perfectly fit into a 2026 wardrobe, and they feel just as modern. If you find good ones, they’ll have aged beautifully. Mine just get better and better the more I wear them, wash them, and live in them. The big oxfords I have from the ’90s are similar. The fabrics just keep getting softer, the colors get a little more washed out in the right way, and they just feel great to put on.

Tell us about your personal style. It feels very classically Polo.

The older I get, the more confident and comfortable I get with the things that I like. When I first got into clothes, it was very grounded in classic, mid-century, American style. In high school I would wear desert boots, chinos, and oxford shirts. As I moved into my 20s, I was interested in the runway fashion world, streetwear, sneakers, going down different paths and trying things out. Not all of it worked, and there are certainly outfits that I look at from the past and say to myself, ‘What was I thinking?’ But it’s all part of the journey of style. I’m 34 now, and I’ve kind of gone all the way back to the beginning. I’m wearing desert boots, chinos, and oxford shirts again, like a very classic American style. My journey now is not necessarily about finding the brand-new item or the cool new trend but really drilling into what’s the best version of what I love.

So it’s not just about having the most covetable, or most expensive pieces. You can have great personal style just by wearing very classic wardrobe essentials.

Absolutely. Take something as classic as a navy blue mesh Polo shirt. Two people can wear it in two entirely different ways, just by the styling details they bring to it. You can learn those moves from the mannequins in a Ralph Lauren store, where they use all these personal styling touches that make all the difference. I’m a big proponent of finding ways to build your own personal style around your closet staples and using that as the foundation to express yourself. One of the outfits I wore for the photo shoot was a blue oxford, white pants, and black shoes, and I call that my outfit nucleus, which I think of as the core pieces you love and from which every outfit spawns, in one way or another. For me, it’s usually that blue, white, and black combo, which is what feels like the most perfect encapsulation of my personal style. And if I ever feel like an outfit isn’t working, it’s probably because I wandered too far away from that core idea. Crazy colors, patterns, fits— there are other people who do that super well, but it’s not my strong suit. I always feel my best when my outfits are simple. Of course, you can splash it up a little with interesting elements, like a patchwork chino or a graphic sweatshirt. But I feel the most confident, and the most like myself, when I’m wearing simple, classic things. And what better place to find those pieces than Ralph Lauren?

What’s still on your grail list, for your own vintage collection?

There’s this Polo anorak from the ’90s with an Italian Riviera poster print design that I think is one of the coolest pieces of clothing, ever. It would be one of the more wild additions to my wardrobe. I always come across Ralph pieces. If you’re vintage shopping for just about any kind of garment—jeans, leather jackets, knitwear, loafers, anything—odds are that one of the very best versions of that thing is going to be from Ralph Lauren. Because from the beginning, Ralph’s entire ethos was not reinventing the wheel of these classic menswear pieces but creating them with quality and integrity, so that 40 or 50 years later, they’ve held up to the test of time. It’s kind of a cheat code to just add “Ralph Lauren” to any search when you’re looking for something vintage, no matter the product category.

Got any good secrets for successful vintage shopping?

Check the measurements. I won’t touch a listing if it doesn’t have measurements, because a medium is not a medium across the board. If you have one great sweater in your arsenal that you know the measurements of, and those can just live in the back of your mind, then it just makes shopping for vintage stuff that much easier. Also, patience is key. I’ve been burned by trying to rush, shopping for a certain wash of jeans that I wanted to wear the next week, for example, and just going with whatever looked like the best option right then. So just be patient, know your measurements, and keep at it. It’s not always gonna work out, but if you follow those, your success rate will be much higher when you finally pull the trigger.
ANDREW CRAIG is the former men’s content editor for Ralph Lauren.
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