A huge thank you to my friend Rob Kelly (Chief Meme Officer at Throwing Fits), who wrote this piece, and Chris Fenimore, a phenomenal menswear and fashion photographer in NYC who shot this, for making this piece come to life.

Please follow their work!

Years ago, on a rainy December night

I met Lawrence Schlossman, founder of the cult menswear blog Four Pins and current co-host of Throwing Fits, as he covertly shuffled Ezra Koenig through the grungy midtown offices of Barstool Sports.

If not for his herringbone Abercrombie overcoat (and the Grammy-winning frontman of Vampire Weekend on his arm), he could have been mistaken for an everyday employee of the flagrant sports media giant. 

Schlossman’s fashion bonafides (Larry, as he’s known to fans of Throwing Fits) are endorsed by a diverse cast of designers, editors, and artists—many of whom make up the laundry list of guests on Throwing Fits.

But it’s his willingness to lean into his non-fashion side, a born and bred New Jersian with fraternity letters from Wake Forest, that have made him a magnet for a growing swatch of men interested in engaging with fashion. 

In the years since his podcast (Failing Upwards) was killed by Barstool, the same fate his YouTube series (Fashion Bros) and blog (Four Pins) all met, he’s settled into seemingly solid ground, alongside his longtime media partner James Harris, with Throwing Fits (for which I’ve managed the social media for since its post-Barstool inception).

At Sprezza’s gracious behest, I took a moment to pick Lawrence’s brain to see what he’s learned from the journey—both tangibly and abstractly—and understand how it’s affected his personal wardrobe, grasp on trends, and more.

Everywhere you look in menswear right now you’re seeing some sort of revival of the #menswear aesthetic whose last iteration you helped pioneer during the Tumblr and Four Pins days. Are you surprised to see it come back so hard or was it always inevitable to some degree?

I’m definitely surprised at how hard it’s been coming back, mainly because of how far the pendulum swung immediately after that era. From 2009 to 2012 you’ve got the end of the urban woodsman look that leads into #menswear. I like to use Watch the Throne as the line of demarcation. Immediately after that is when streetwear and the high fashion version of it 1000% took over.

Of course, there’s always classic men’s fashion that’s been around since before we were born, but in terms of it being a “cool trend”, I never thought it would have this much-staying power, to be honest.

What looks or pieces have you been the most surprised to see come back around?

Raw denim, for sure. I was never a big raw denim guy. I obviously had some APC New Standards back in the day, when people were doing ocean soaks and putting them in the freezer and shit. I didn’t expect that really hit again, especially since the vintage [Levis] 501 look is getting so much love from everyone from Dimes Square skater kids to the TF jawnz enthusiast type. 

Are there any parts of the 2012 #menswear era that you’re surprised haven’t caught on in the current revival?

I would have thought, as suits have come back, you’d see more Neapolitan, unstructured stuff. Everything with suiting right now feels very structured, I guess. You obviously still have that sleazy side that people are into and the idea of the Georgio Armani power suit feeling fresh again.

Of course, those can be loose and comfortable in their own way, but it’s never as easy to throw on as a soft-shoulder jacket. Those don’t feel super trendy for whatever reason. Blame the Pitti peacocks.

Both raw denim and structured suiting have a relatively high barrier to entry, not just when it comes to money, compared to the other side of their respective coins. 

Yeah, like flared trousers, for instance. Those are trendy right now, and I get the appeal of a bigger, fuller trouser with some break, but when you look at it in a vacuum, that’s a crazy entry point. That’s way harder to wear versus back in the day when guys were getting into Neapolitan suiting because it’s just so easy to wear, you can take it off, throw it on a chair, and it’s going to keep its shape no questions asked. 

Are there more style resources around nowadays that might convince a guy to go straight for the flared pant instead of playing it safe?

There’s more information as our world has ballooned, without a doubt. When I was coming up, there were like 10 acceptable blogs to read, and then you could go digging in the forums if you wanted to go deep.

Now things are more visual and, to some degree, it feels more like we’re dealing with hubris. Guys see something they like from someone they follow, they ask what brand it’s from, and then they go and buy it. You can skip a bunch of sometimes almost necessary steps that way. 

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So things have become more accessible? Obviously, the other side of that is a convo around overconsumption…

I’m always going to recommend doing your research and doing the work before you spend your hard-earned money. But yeah, I think that’s just how the world is with mood boards and influencers. No one is complaining that they don’t see anything cool online. In fact, there’s maybe too much stuff out there. 

Like crazy suits

You see something you like, your brain goes, “I want to be that,” and you try it. It’s still gonna take time for you to figure out how to wear it and how your personal style can amalgamate via that purchase. On a positive note, I think it’s cool to see guys willing to take that risk now.

I remember in—I think it was around the summer of 2020—you started wearing loafers with Patagonia baggies and some sort of Oxford shirt up top—like a southern dad who just got done mowing his lawn. I thought it was kind of ridiculous, but sure enough, within a few weeks, the Fit Check Friday on TF was flooded with dudes trying it out for themselves. I was floored, to be honest. 

I’m flattered. I mean, I do love that. Bottom line is that I get inspired, too and see things all the time that I want to try to pull off. If you see one of my outfits, hopefully, it’s not just a paint-by-numbers version of a look I saw but an element of it. Like recently, I pulled back out my wheat Timbs because I saw my friend Mikey wearing wheat Timbs and it looked sick. 

I think a lot of fashion people see being influenced as something to be ashamed of

Everything is a reference, right? Even if it’s a holy original idea, there’s some kernel of something from somewhere else. That’s the way I approach it. The more good taste in the world, the better. 

You’re someone who likes to engage with trends

I love trends. I’ve said it before, but I believe it deep down in my nuts that personal style is a journey with no destination. It’s always gonna change. It’s like a train ride with a million different stops, and you’re free to get off at every single one and poke around if you want. Things are gonna have moments and cool down. Yes, everything is moving a lot faster now, but you can always wear something again later down the line. 

You’ve never fully been a capital “f” Fashion guy, but I want to get your thoughts on menswear sort of being the hot, sexy thing going on in the circuit, even compared to women’s 

The exciting stuff happening in our world, New York City, is mostly small, independent labels. I wouldn’t really classify any of them as capital D designer. But there’s obviously more men interested in clothes now, and that influences things.

Virgil Abloh, probably more than anyone, is who we have to thank for that. And I mean that sincerely; I think it’s cool more guys care about fashion. Streetwear and sneaker culture are all about hype, which has been absorbed into the designer world. There’s more money, and more money means more attention.

So the tide rises; what happens next?

I still think people will age out of streetwear and sneakers, move away from that flashiness, and start building an actual wardrobe. People grow, and their clothes grow with them. The flashes—take Tiffany x Nike as the latest example—I think a lot of people are disappointed with this stuff. You get hammered over the head with collabs and cash grabs that are designed to be financial instruments. Enough of that will create some level of disillusionment, right?

I guess we’ll find out

Perspective comes with age. That’s just maturity. There’s this ballon in the middle right now, but I think there’s just a more cerebral way of dressing. I welcome those guys with open arms whenever they're ready. I kind of get killed for calling it “grown man streetwear” cause it’s not really streetwear, or I guess maybe that’s the point.

Now it’s kind of just…

Grown men?

Yeah, eventually, guys are naturally gonna find themselves in a mental place where it’s like “oh, what’s going on over here?” and there’s a market for that. Hopefully, it’s more conscientious consumption and buying things for the right reasons.

I don’t really have a prediction. I just think it’s a journey. I’m glad that sort of flow exists right now. And listen, I know of a certain podcast they could listen to if they’re trying to figure that all out. 

Most stylish person of all time? 

This is the easiest question of all time. Apologies to Hov, but Jack Nicholson invented swag. End of story.