Matzo Ball Billiards

Somewhat recently, I posted a TikTok that contrasted a montage of some of my very best fall/winter outfits against a somewhat dorky summer outfit I happened to be wearing on that particularly toasty day. The punchline was simple.

Fall and winter allow me dress like a man of mystery. A man of intrigue, culture, and severe pretentiousness. Almost always with a long-ass coat. Summer, however, forces me and most men to dress like a toddler at best, and a miserable little gremlin boy at worst.

The video did extremely well. I think it might be my biggest one to date, in fact.

2.7 million views at the time of this writing. 490K likes.

Something there resonated with people. Part of me likes to think that they mostly appreciated my style during the fall and winter. I received a lot of supportive comments and gained a ton of new followers. That, along with another recent viral video of me dorkily grooving to The Game of Love by Santana and Michelle Branch, recently catapulted my account from barely 10k all the way to nearly 15k!

But the other component of the video that people seemed to relate to was its punchline – summer fits can be a struggle, after all.

Ironically, I kind of like the summer outfit I was wearing for its dorky and earnest charm. The bottom half consisted of a pair of vintage high-rise, pleated green shorts by Tommy Hilfinger that I recently got on eBay for like $20 as the temperatures began to climb.

One thing you must know about me is that I quite like pleats. To be honest, with a few exceptions, I find it hard to wear flat-front pants nowadays – they just seem a bit boring in comparison, at times. And when it comes to shorts, I’ve been experimenting with wider silhouettes and slightly longer cuts in recent years. So, it was natural for me to start wanting them with pleats.

I’ve seen many on TikTok champion this look for a bit now, often referencing vintage Ralph Lauren lookbooks and J. Crew catalogues, not to mention Laura Dern in Jurassic Park.

To me, these are some killer shorts, with far more depth and dimension than your typical pair of flat front chino 5-inch inseams – and it’s a style I’ve been chasing more and more.

That said, the shorts were basically all I actually liked about the outfit in my video. It was a burning hot day, and when it gets really toasty, all I think about is survival.

Which meant pairing it with a roomy cotton tee, comfortable sneakers, and not much else.

The result was a bit childlike. Possibly in its simplicity, though the horizontal striped shirt didn’t do me too many favors, I suppose. It wasn’t an abhorrently bad outfit. Again – I like the shorts! Not to everyone’s taste sure, but I’ve been styling them a lot lately.

(I didn’t even notice that the pink cotton-linen blend shirt I’m wearing above was heavily channeling Laura Dern until writing this. Lmao.)

The problem is that we seem to equate complexity in fashion to maturity and taste. And to some extent, I think there’s some truth to this. The more components you add to an outfit, the more mastery over each it requires. For it to work, things need to be just so. Which is all the more impressive when you can pull off a sophisticated, multi-layered ensemble.

Any fashion fella with two brain cells will be quick to tell you that layering is the simplest way to add interest to an outfit. And I’m someone who is downright obsessed with tailoring, which means sport coats and overcoats are a mainstay in my fall/winter layering endeavors.

Summer strips that all away. At best, we fellas can manage a camp collar shirt worn open over a ribbed tank top. I think this is a perfectly good look, but there’s no denying its casual nature. There’s little room for sophistication or playing with smarter aesthetics.

Some menswear heads will jump to claim that you can wear tailoring in summer fabric like linen, seersucker, and tropical wool. And truth be told, they’re right. I just haven’t been fortunate enough yet to cultivate a summer tailoring collection.

That said, New York City gets hot as balls. And I dare to argue that during much of the summer here, where it is regularly 90 degrees with intense humidity levels, even summer tailoring is too excessive.

The best you can do in this boiling hot city is wear shorts, a tee, and pray for October to hurry the fuck up.

But we do get to have a bit of fun when it comes to this forcibly casual dress code. I do like a classic 5-inch short, but as you can see, I’ve also incorporated my love of pleats into my shorts rotation. I technically started this last year with this pair of cotton-linen blend shorts from Madewell, styled recently below.

You can’t see so well here, but these are pleated, too. I also really like this shirt – authentically made in Hawaii and 100% linen. Thrifted it in a Fort Lauderdale Goodwill a couple of years ago. Look at that bold pattern! I think it goes great with my 70s coke-dealer shades.

I also think you can still get away with normal pants and jeans throughout the summer on more mild days, provided they’re roomy enough to allow proper airflow. A couple of months ago, I finally picked up the Japanese Loomstate Full Saddle Jeans by Buck Mason, as featured in my Watch & Wear: Spring/Summer 2024 post, and they pair really nicely with this vintage L.L. Bean chambray shirt.

Also, get a load of those vintage Giorgio Armani derbies! Recently picked those up and love ’em.

But back to shorts and their fun varieties. Even more recently, at long last, I decided to jump aboard the jorts train. I just got this pair from Madewell on clearance, and I’m a bigger fan of them than I initially thought I’d be.

The light wash is ideal for summer, and they’re fairly roomy, too, with a generous rise and sturdy construction.

I feel like I’ve somewhat come full circle with these. As a kid, I couldn’t figure out how to match shit, so my mom just sent me off to summer camp with a bunch of pairs of denim shorts because they “went with everything.” Now, we’re back at it again with the jorts – but this time in like, a really tasteful and stylish way…I promise!

One summer aesthetic I’ve been hoping to achieve is a true white-on-white linen-based outfit. It should be no secret that Niles Crane is somewhat of a menswear reference point for me, and I love his whole look during the heatwave episode, Daphne Hates Sherry (Season 4, Episode 21).

The white linen shirt on white linen pants is a bold combo, and even played for a brief laugh as it’s so radically different from Niles’ usual double-breasted suits and geometric ties, but it does look good! I love how billowy it is, and of course those pants have some sick pleats.

I’m currently in the market for pieces to recreate this look, though it’s taking some time. Not seeing much in the secondhand market in term of pants, really. I like the Tanger trousers from Casatlantic, but they’ve been out of stock for a hot minute. No matter, I’ll bide my time and review other options.

Heck, maybe it’ll just be a project for next summer. We’re already halfway through this one, after all, and I’d rather save my money for more vintage Armani, a la Niles’ typical form.

To be frank, there really isn’t any sort of grand thesis to this somewhat messy blogpost. I just thought it was interesting how much summer style can differ from peak layering seasons, if only by necessity. If I could choose, it would be a crisp 60 degrees almost year-round – perfect for a knit sweater and a nice jacket. Or a sharp DB suit!

Alas, it gets pretty hot around here. And it’s only getting hotter. Instead of fully abandoning my stylistic morals, I have been making some attempt to uncover what niches of summer style actually speak to me. I think it’s helped assuage the despair I feel, at least somewhat.

But underneath my dorky pleated shorts and Hawaiian shirts, I’ll secretly be counting down the days till October. It can’t come soon enough.