It’s crazy to think how fast time flies when you’re an adult. When I was in high school, it always felt like Thanksgiving break was eons away. Now, it feels as if I went straight from my birthday to Jay’s yearly Friendsgiving dinner. This isn’t a bad thing– it’s nice when a year is mainly filled with good times with friends, at least in my biased memory. After all, my whole thing is that I enjoy Hanging Out With Friends!
I may be the instigator of casual, impromptu hangs but it’s Jay who is a true planner and host. Long time readers of the blog will know that I have attended his annual Friendsgiving for the past eight years. It’s quite special for me, as he started it mainly for his high school friends to see each other during break; I was just a suit-wearing stranger from the internet, serving as Spencer’s plus one. The guest list has obviously expanded exponentially over the years, ranging from Jay’s friends from college and work (a few end up becoming my friends as well) to also including people I’ve introduced him to. In short, Friendsgiving is an incredibly wholesome evening that everyone looks forward to.
Last year’s iteration was quite small, as a few people weren’t available; as a result, it was held in his apartment. It was cozy, being a mixture of a dinner and slightly more-than-intimate kickback. However, this time he was able to reserve the Events Room at his apartment which really opened up the guest list. Instead of having about 15 people, we doubled it to a little over 30, with more friends (and their significant others) being canonized into both Jay’s and my fold (I’m always recruiting for trivia).
Everyone brought something delicious, whether it was a meat dish, veggies (I made roasted broccoli, or home-mixed potables. I think you can tell from the photos that everyone was full, tipsy, and happy. What more could you ask for!
The reason I write about Friendsgiving every year isn’t just because I like to diary-ize my life (I mean I do whatever), but because it is a bit of a menswear event in a sense. Ever since high school, Jay has been into dressing up even if he’s one of the only ones (well, it was him and Spencer). So like me, he’s all about creating a context conducive for getting a fit off. As a result, Friendsgiving has always had a dress code.
Jay’s Partiful invite stated: “the dress code is smart casual – basically just wear something nice and a little dressy”. It’s a general one, but with enough direction to ensure people don’t show up in a tee shirt and shorts, a common sight in Orange County. And to their credit, all of the attendees do look nice! But for the menswear guys, it’s a fun challenge to get something that is decidedly fall, at least to our own standards. We’ve done variations of ivy and vintage as well as utilized tweed, corduroy, and layers up the wazoo. Each year’s fit may be “new” in the sense that we’ve never worn the specific pieces before, but we always try to get the most out of what we already own. And let me tell you, 2023 might just be our best dressed one yet. It’s always just us who are the ones in a tailored jacket (let alone a tie), but hey, we don’t mind Standing Out, especially when we’re among friends.
I really loved what I wore to Friendsgiving 2023. It’s got an incredibly vintage vibe as well as one that feels appropriate for the season; in fact, this might be the first time I’ve intentionally leaned into that mood.
This is mainly due to the plaid shirt, a deep red/green plaid number from Brooks Brothers done up in their rare point collar variation. The point collar makes it able to be read as Esquire Man than ivy league student, which I always like. However, I decided to change it up slightly by subverting expectations (my own). The Esquire Man would have probably paired the shirt with a stripe or perhaps a foulard; an ivy guy would have worn a motif or knit tie. Instead, I did a move that I believe I’ve seen in an old movie or photograph (that I unfortunately can’t find anymore)– I did double plaid with an orange/brown 1940’s tie. Suddenly the fit feels a bit more late 1940s but more “homegrown” instead of being what a Golden Era movie star would wear.
This is further emphasized with my thrifted 90s brown jacket which thanks to it’s interesting cloth, passes quite well for a 40s/50s jacket extremely well. Again, Esquire man and the Ivy Leaguer would have probably worn a solid jacket or perhaps something more “classic” like a houndstooth or plaid. No, I wanted to have fun.
I kept the earth tones going with my caramel trousers and my color 8 tassels; cream socks provided a bit of breather as well as marked my outfit as more “casual”, at least compared to my navy sock fits.
I feel like this outfit may have unlocked a subgenre for me this season. Instead of pairing my plaids with plain clothes, I can have a little fun with it! You can probably expect to see more of this shirt and tie this season…just worn with different things. 😉
The other guys looked amazing too!
MJ decided to make me sad by wearing one of my favorite garments that I have since grown out of: the Camoshita flecked suit. It has quite a slim leg that I would definitely not wear today, but the whole vibe is great: in addition to the suit’s fantastic cloth, it also has a lovely lapel and soft shoulder. It’s one of the reasons why I made sure to get a standalone SB jacket with my green cotton suit. I wanted to keep that feeling alive!
I liked that MJ went a bit Ethan (or Armani?) by pairing the flecked suit with a grey-blue point collar shirt. It’s honestly a little unexpected for him but I enjoy it; I guess we all feel like Frasier every once in a while. MJ does bring right back to himself by wearing a green and red block stripe tie (MJ’s love of colors is a tenet of his style) as well as green camp socks with paraboots.
Spencer was concerned that we’d be too matchy matchy when he heard what my outfit was going to be. We share our fit ideas in the group chat just to avoid unfortunate faux pas; I think it would be quite funny if it actually happened, but so far it isn’t.
Like me, he wanted to wear a red plaid shirt. However, his was a sportshirt not a point collar, which made it interesting when he decided to wear it with a tie. On top, he wore a honey colored summer-tweed jacket (wild!) which played quite well with the reds and browns on his chest. To give it more of a casual vibe, he went with his least-torn jeans and added some cowboy boots. In the end, he also feels quite 1948 but perhaps in a different USA location.
Jay did an Armani-esque vibe last year (with a charcoal suit and khaki shirt/tie), but this time he decided to be a bit more casual while retaining a bit of rakishness. He opted for a suit, wearing a 1960’s brown sack that looked fantastic with a gray cashmere sweater and bandana (a true Jay staple). He also brought me back to the past with his shoe choice: black suede cap toes that I gave him way back when.
I’m glad that all my friends are able to give my old clothes some life, especially when I can see it in person. In that way, it’s like I’m having a Friendsgiving with my clothes, past and current.

Now enjoy a plethora of photos from the evening. This might be the most I’ve ever taken at a Friendsgiving due to the sheer number of people as well as the open space to move around. I really do think you can see just how fun this one was!
God, I just know that I’m going to blink and it’ll be time for the 2024 edition in no time.
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Always a pleasure,
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