Watch & Wear: Fall 2024

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My God, this has taken me far too long to get to. I don’t exactly make it much of a secret that fall is easily my favorite time of the year for putting together my silly little outfits. I’m not alone in this sentiment either – real autumnheads know that October – November is the peak season to be dressin’.

I suppose I’ve been a bit busy lately. I work three jobs, after all. I’ve also become increasingly neurotic about my spending habits. Which, as someone who loves clothing, has clashed a bit. I’ve bought very little the last couple of months in an effort to save money. But that doesn’t mean I haven’t been eyeing some pieces – I’ve just been trying to be a lot more intentional about it.

This being the second ever Watch & Wear that I’ve written, I suppose I should reintroduce the concept. Here, I go over some fashion-related items that I’m currently watching – pieces I’m highly tempted to buy, followed by recently acquired items I love, and finally, reviewing some old favorites.

Wears I’m Watching.

New Wears.

Well-Worn.

A bit clumsy, but I thought the wears/wares wordplay was awfully clever when I came up with it on the toilet one eventful day last spring. So, that’s the drill. Now, let’s get in the soup.

Wears I’m Watching: Ties That Knit, Vests of Fair Isle

I own a lot of ties. Roughly 40 or so if I had to guess, which is odd considering that I mostly just wear them on the Sabbath weekend. But this is largely due to the fact that 95% of my ties are silk and lean formal. While I don’t often wear my more formal suits during the week, I do wear a lot of casual tailoring. Corduroy suits, tweed blazers, etc. I usually go without a tie when wearing these pieces, either wearing an oxford shirt, a turtleneck sweater, or some other casual top.

But if I owned more casual ties, I think I’d like to shift this a bit. I recently acquired a nifty vintage wool tie from Scotland with a fringed edge, and it’s only furthered my curiosity. It’s actually rather surprising that I don’t any knit ties, and I aim to correct this in the near future.

I don’t have any specific ones picked out, as I’ll likely source them from eBay, but I’d like a maroon one and a dark green one for starters. Shades of brown are always welcome, too.

I can just imagine how fun it’ll be to insist that I’m actually “dressed down” while actively choosing to sport neckwear on a weekday.

I’ve also been absolutely itching to get my hands on a nice Fair Isle sweater vest. I own two inauthentic Fair Isle knits from J.Crew that I like quite a bit, heck, one of them is probably my favorite sweater alone due to its color choices.

But I’m also a sweater vest boi. I think they’re fun, sue me. I mostly wear the cardigan button-up variety, but I think I’d prefer a pull-over Fair Isle option. Sans sleeves, of course.

I just think they look awfully smart when layered under a tweed sport coat and the like. Very academic. I think I would have gotten one sooner if they proved easier to track down on the secondhand market in my size. There’s a ton of vintage Ralph Lauren options on eBay at any given time, but they’re either well over $100 a pop or only available in sizes like L and XL.

I might just have to bite the bullet and buy one that’s new. In which case, I might go for this one by Jamieson’s.

It’s among the better values I’ve seen made from authentic Shetland wool. But we’ll see – I’m still holding out for a vintage find!

New Wears: A Better Oxford Shirt + A Rad Thweed Piece

For someone who wears a lot of Oxford shirts, most of mine have been surprisingly shitty. One of them is a beat-up, shrunken blue OCBD from Target I’ve worn since college. The rest are passable options from GAP and J.Crew I acquired secondhand at the thrift. They’re not bad, and tbh, I like the rougher oxford cloth they’re made from, but they all share one major design flaw that I’ve grown to dislike a great deal.

The collars. Are too. Small.

These shirts are products of the mid 2010s, I imagine. During the height of bad business casual’s reign. That means, no ties, or if weird skinny dandy ties I can’t stand. So, the shirt collars aren’t built to accommodate neckwear, really.

I’d long wanted a better OCBD, and it’s kinda hard to have that conversation in classic menswear spaces without bringing up J. Press. They’re something of an ivy style legend, and I’ve been tempted to give their shirts a try for a long time.

But remember, I’m in my scrooge era. I wouldn’t let myself buy one new – so I snagged this lovely blue/white stripe oxford off of eBay recently for like $25.

And I’m pleased to report: it’s great! It has a fairly flattering fit, a slightly finer oxford cloth than I’m used to (I admittedly prefer them rougher), but the best part is – it has a high, generous collar. No wimpy points here. Easily enough room to fit that vintage Scottish tie I mentioned earlier.

I like to think I’ll be wearing this shirt at least once a week from now on.

I got this shirt pretty recently. But before that, I hadn’t bought anything in over a month – which is crazy for my secondhand shopping-addicted ass.

That said, my previous purchase was a super duper cool one, for lack of better terminology. While browsing vintage suits on eBay, as I do literally every day, I came across a three-piece tweed by once legendary, Chicago-based department store Marshall Fields. I dropped a bit over $100 on it, but it was a wise choice.

This thing is awesome.

For one, it’s made from a rich, broken-in tweed with Donegalesque flecks of color throughout.

And most notably, get a load of those postbox pockets on the jacket! I could store all of my Bionicles in there. Very handy.

It fits like a dream, and the leg has a nice bit of flare to it which leads me to suspect this is a 70s relic.

Admittedly, I haven’t worn it much yet, mostly because it’s been a very warm Autumn, but we’re getting there. I expect this will become a new favorite to be sure.

Well Worn: Shiny Armani & Bean Boots

Slowly but surely, I’ve been making small improvements to my shoe rotation. It’s still nowhere near where I want it to be, but in the last year, I’ve been rocking a few cooler kicks.

First up are my Giorgio Armani derbies I got on The RealReal for around $50 or so last spring. If you know me, you know I love old Armani anything, and these fit the bill. They’re a deceptively dark brown that almost appears black depending on the lighting conditions and feature a pretty cool shine.

Derbies are a casual shoe, and I mostly treat these as such, but I also think they look kinda great with my vintage 80s Cerruti DB suit. They’re made from a really solid leather and make a truly satisfying sound when I walk in them – hell, they make me feel at least 10x more important than I actually am.

On a different side of the shoe spectrum, there’s the matter of my L.L. Bean duck boots that I purchased last winter. I’d wanted a pair for years, and I’m glad I finally got some, because I low-key get excited when it rains, and I get to break them out.

To be honest, I wear them on perfectly dry days, too. I love the color scheme I chose, as well. The mallard green rubber bottom and the dark brown full-grain leather upper fit perfectly with my existing wardrobe, and I can hardly think of a pair of shoes/boots that perform as well as these do for me.

They’re supremely comfortable and nicely made. Kinda shocking that they’re only like $150!

Wear To, Next?

I couldn’t tell ya. Like I said, I’ve slowed down my purchasing habits a lot as of late, so I’ll probably just be focused on enjoying the clothes I already have for a while. I’m also sorta maxxed out on closet space, I’m embarrassed to admit.

Who knows, maybe I’ll fall into fabulous wealth sometime soon, and I can move into a sexy prewar apartment on Central Park West with abundant closet space! A guy can dream, can’t he?

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