My Internet: Jake Woolf
The menswear creator has had positive and negative experiences with virality.
Embedded is your essential guide to what’s good on the internet, written by Kate Lindsay and edited by Nick Catucci.
Most weeks, we quiz a “very online” person for their essential guide to what’s good on the internet.
Today we welcome Jake Woolf, who covers men’s fashion in his newsletter; on TikTok, Instagram, and Twitter; and in GQ (where, disclosure, I am U.S. site director). Jake recently upset a few people by arguing that shorts are best worn with quarter length socks and listens to a playlist of all of the Drake and Kendrick Lamar diss tracks when he runs. —Nick
EMBEDDED: What shows up on your TikTok For You page?
JAKE WOOLF: A lot of the stuff you might expect, like style videos, GRWMs, things like that, but also NBA clips (shout out to awfulcoaching, he’s my favorite right now) and a lot of car videos. Which is great just because it’s a reprieve since I’m always thinking about clothes. If I’m being honest I’m probably more likely to sit through two and a half minutes about all of the features of a new Kia Sorento than something style related.
EMBEDDED: Do you make TikToks? What format works best for you?
JAKE WOOLF: I do. Green screen shopping videos are the ones that usually do best.
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EMBEDDED: Do you still tweet? Why?
JAKE WOOLF: I do, because sometimes it’s a better venue to just say something specific about a thing I like, whether it’s a piece of clothing, a brand, whatever. IG stories are good for just showing something I like, and TikTok feels like it requires a bigger explanation or contextualizing, but Twitter I can just be like “I got these shoes and they’re dope,” and that’s it. It’s also been a nice promo tool for my Substack.
EMBEDDED: What do you use Instagram for?
JAKE WOOLF: Instagram for me is the most all-encompassing app. I use it for Reels (both making and watching), showing off stuff I like on Stories, and talking (read: sending memes) to my friends.
EMBEDDED: What types of videos do you watch on YouTube?
JAKE WOOLF: I spend a silly amount of time watching car videos, particularly late at night haha. There are a few creators that I cycle through, like Doug Demuro, Savagegeese, The Straight Pipes, Throttle House, and TheTopher. They are all a little different, so even when they all post about the same car within a few days it’s fun to see all of their different takes on it. The only thing that comes close to car videos are, like, old movie or TV show clips. And I guess celebrity interviews.
EMBEDDED: Where do you tend to get your news?
JAKE WOOLF: I’d love to tell you I’m reading a hard copy paper from a prestigious news organization every morning, but yeah, it’s Twitter. But I will say harder than ever to sift through the hot takes and just get to the “what is actually happening” part.
EMBEDDED: How do you keep up with the online discourse? How important is it to you to do this?
JAKE WOOLF: People in menswear have a lot of feelings about, well, a lot of things! Which I see on Twitter and IG. I used to feel more inclined to participate, but as I’ve gotten older I find it harder to keep up with every twist and turn. I will say memes make it easier though. If you just follow Throwing Fits on IG you’ll get a pretty good idea of what’s happening discourse-wise, though you also might realize that you’re online WAY too much.
EMBEDDED: What’s the last strong opinion you had about a story, topic, or controversy online?
JAKE WOOLF: A few people were upset that I said quarter length socks are the best socks to wear with shorts. They’re longer than ankle socks but shorter than crew socks, and though I think everyone is entitled to their opinion, for me, I stand by my claim. I just don’t like the way crew length socks look bunched down or fully pulled up.
EMBEDDED: Where do you usually discover or learn about online trends?
JAKE WOOLF: In order: Twitter, the group chat, TikTok, then IG.
EMBEDDED: How do you find recommendations for what to watch, read, and listen to?
JAKE WOOLF: The group chat.
EMBEDDED: Do you have any favorite media company newsletters?
JAKE WOOLF: I swear I’m not trying to pander, but I genuinely do like to see what Chris Black has to say in his Pulling Weeds newsletter for GQ. He’s a take master, so it’s always fun to see what he’s into or upset about on any given week.
EMBEDDED: Are you into any podcasts right now? How and when do you usually listen?
JAKE WOOLF: I most often listen to The Big Picture and The Rewatchables, both of which are run by The Ringer. I listen on Spotify in the car or on the train.
EMBEDDED: Have you had posts go viral? What is that experience like?
JAKE WOOLF: I have, and I guess it depends on why something went viral. I’ve had positive and negative viral experiences, both dealing with, as you might expect, opinions on clothes. The positive ones are easier mentally for sure, but then you can kind of get caught in the feeling of “I have to repeat that success by doing everything the same way I did last time” and it usually doesn’t work out. At least with the negative virality you can be, like, “Well, I’m never doing that again.” Or sometimes it just illustrates that your post hit the wrong jet stream of the algorithm.
EMBEDDED: Who’s someone more people should follow?
JAKE WOOLF: Brian Park, a comedian and writer. I just looked and am surprised he’s “only” (it’s all relative!) got about 38K followers because his stuff is so good. He posts these very funny solo skit takedowns of self-serious creatives and corporate culture. Like, “POV: you’re on a date with a creative director.” So if you’re reading this, don’t just wait for the videos to hit your algorithm … toss bro a follow!
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EMBEDDED: Which big celebrity has your favorite internet presence, and why?
JAKE WOOLF: Honestly I think I like it most when celebrities just aren’t online, or pop in like once a year to post something, get everyone talking about it, then bail. I’m probably just jealous of that level of freedom.
EMBEDDED: Do you typically start searches on Google, Reddit, TikTok, or another source? Have you found Google’s “generative AI” summaries helpful?
JAKE WOOLF: I’m a pretty dang good Googler, which can sometimes lead to Reddit. Tiktok’s search isn’t really equipped to find the specific stuff I’m usually searching for, like the exact sweater a celeb is wearing or something.
EMBEDDED: Do any of your group chats have a name that you’re willing to share? What’s something that recently inspired debate in the chat?
JAKE WOOLF: Jawnz Enthusiasts. We’re kind of always arguing about something, but recently, and I guess ironically, the movie Civil War got the chat pretty fired up.
EMBEDDED: What’s your go-to emoji, and what does it mean to you?
JAKE WOOLF: Sorry to Gen Z, but I still use the crying laughing emoji all the time. I just don’t buy that the regular crying emoji conveys the same thing.
EMBEDDED: What’s a playlist, song, album, or style of music you’ve listened to a lot lately?
JAKE WOOLF: I compiled all of the Drake and Kendrick diss tracks into a playlist and have been listening to it on runs.
EMBEDDED: Do you pay for a music streaming service, and if so, which one? When was the last time you bought a music download or vinyl record, CD, or tape?
JAKE WOOLF: I pay for both Apple and Spotify. This is my take: Apple is better for music, Spotify is of course better for podcasts, so that’s how I use them.
EMBEDDED: If you could only keep one streaming service for TV and/or movies, which would it be, and why? In general, do you prefer to get ads or pay more for ad-free tiers?
JAKE WOOLF: MAX, maybe? I honestly can’t keep track of which service has what anymore, but that seems like a good choice. I just kind of pay for all of them, which probably isn’t good, and I pay for ad-free.
EMBEDDED: What’s your favorite non-social media app?
JAKE WOOLF: Capcut. I don’t know if it’s my favorite but it’s definitely the one I use the most, and I can’t deny that it’s pretty amazing what they’ve been able to do in terms of mobile video editing.
EMBEDDED: What’s the most basic internet thing that you love?
JAKE WOOLF: Beautiful photos of mid-century modern homes and vintage cars.
EMBEDDED: Do you regularly use eBay, Depop, or other shopping platforms? What’s a recent thing you’ve bought or sold?
JAKE WOOLF: I use eBay all the time. Grailed sometimes. I just bought a vintage Nascar T-shirt for a video I’m filming soon on eBay. As of this writing it hasn’t arrived yet so I’m not totally sure it’ll fit, but either way it’ll still get used in the video. This will make sense soon!
EMBEDDED: What’s the last thing that brought you joy online?
JAKE WOOLF: Mk.gee’s Jimmy Kimmel performance. He changed up his song “Are You Looking Up” to be a lot more yacht rock-y, and I loved it. I also just in general love seeing up and coming artists kill it during their first TV appearances like that.
Thanks Jake! Subscribe to his newsletter and follow him on TikTok, Instagram, and Twitter.
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