Watch & Wear: Fall 2025

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Is this thing still on?

Sure seems like it. A couple of days ago, I got an email from WordPress notifying me about an upcoming annual payment, the very one that secures this domain and an assortment of other premium features I’m too lazy to look into.

This was a sobering moment for two reasons. For one, I like to think that I could use that money for other vital things, like groceries, my utility bill, or more pants. My other cause for alarm was the fact that I had failed to publish a new blog post for approximately six months. Not a good look!

So, I’m here to get my money’s worth. And hey, we’re just in time for my favorite time of year to get dressed. Which is why I thought it was appropriate to return with another Watch & Wear for Fall 2025, the series where I feature some fashion-related items that I’m currently watching – pieces I’ve been tempted to buy, followed by more recently acquired items I’ve been stoked about, and lastly, appreciating some old favorites.

Wears I’m watching.

New wears.

And stuff that’s well-worn.

The concept is all in the name of justifying my shopping addiction (secondhand still counts) by assuring you that I do actually like the wardrobe I’ve already worked so hard to cultivate. Got it? Great. Time to talk shop.

Wears I’m Watching: BBC (Big Black Coats) and Turtleneck Time

This is a classy blog. We come here for my lukewarm takes about pleats and my wickedly clever sense of humor. That is to say, I would really like to get my hands on a big-ass black coat this year.

It’s no secret that I love a good overcoat – and to qualify, we need high quality materials, a nice, generous length, and proportions that don’t feel skimpy (big lapels welcome). I already have two great vintage wool outerwear options: my gray herringbone Harris Tweed and my slightly more formal oatmeal herringbone DB coat.

These are both really nice pieces that I get a ton of use out of. But lately, I’ve been itching to experiment with more black monochrome looks. After a rewatch of Eyes Wide Shut (1999) a while back, I was really drawn to Tom Cruise’s look as he roams the city streets.

It’s sleek, broody, and had me intrigued. For much of my life, black overcoats have carried an interesting association from my childhood, being relegated as a piece of the Orthodox Jewish uniform I grew up around and even partaking in to some degree. Black coats were, to me, symbolic of an old and decidedly “uncool” look that I had branched out from.

But part of why the “long black coat” is so often favored in traditional Orthodox Jewish dress is because it represents a combination of modesty and regality. It isn’t flashy – it carries with it a sort of solemn respectability that is both muted and polished at the same time.

Viewing it through this lens, I’m actually quite appreciative of the long black coat once more. Tom Cruise makes it look sick as hell, too, which further improves its standing.

For me, I would greatly prefer a nice, fully wool or even cashmere blend vintage option. Ideally double-breasted, because all that extra fabric creates extra drama, not to mention of course a length that continues well past my knees.

Admittedly, I’ve also been on a big Batman kick this fall. In my personal time, I’ve been enjoying replays of the Arkham video game series as well as rewatches of the many big-screen iterations of the world’s greatest detective.

Bruce Wayne is a stupidly rich guy. And he dresses well, too, unlike most of today’s billionaires who seem allergic to good taste. And one fashionable choice I keep noticing is that the character of Bruce Wayne seems to have an affinity for black turtlenecks.

In particular, both Keaton and Kilmer’s portrayals of Bruce are seen sporting smart, black turtleneck sweaters.

This shit goes hard, simply put. I actually used to wear a black turtleneck pretty often around my college years, but it was a crappy polyester one from H&M. That simply won’t do today – so I’m keeping my eyes peeled for a nice merino wool or even cashmere piece.

J.Crew and Todd Snyder have some nice-looking cashmere options currently available (see below) but I’m obviously more inclined to find something vintage if I can pull it off.

Todd Snyder
J.Crew

Now, just picture one of these bad boys layered with the aforementioned long, black double-breasted coat and you might see the vision. Broody! And certainly a departure from my over-reliance on earth tones. It’s funny that I’m considering black monochrome to be my version of “branching out,” but here we are. lol. lmao.

New Wears: A Solid, Solid Navy Suit, Neat Knitwear, and L.L. Bean Leather

I own too many suits, and at the same time, not nearly enough. I’m a collector, so naturally I am more drawn to unique pieces over simple staples. But by overindulging in this philosophy, I’ve ended up with some ironic gaps in my wardrobe.

A good friend of mine is getting married soon, and I’m one of the groomsmen. He requested that we all wear solid navy suits for this role. Should be easy enough, no? After all, a navy suit is often recommended as the first suit a man should buy – especially if he’s only going to buy one.

Well, guess who, for some reason, didn’t have one…?

To be clear, I actually do own two navy suits. But one of them is a 1980s chalk stripe DB, and didn’t fit the streamlined criteria. I needed something simple and solid-colored.

My other navy suit does technically qualify – but I would rather be drawn and quartered at Union Square than be seen wearing it. It’s a shitty polyester thing, something I bought in college for $100 on Amazon (shudder) and currently resides in a bin tucked away under my bed, awaiting eventual disposal or donation.

Basically, as the “suit guy” in my friend group, it was a pretty funny situation to be in. So, I went shopping.

For several months, I was hoping I’d be able to find a cool vintage deal. I scoured the local thrifts, scrolled eBay for hours, but as the wedding date drew closer and my search had yielded no fruit, I realized it was time to go retail.

I was very particular in this endeavor. If I was going to pay retail prices, I wanted something that I really liked and would want to wear a lot in the future. That meant I was prioritizing versatility in what is already considered a pretty versatile suit color.

After some deliberation and a Sunday spent trying things on all around town, from J.Crew to Ralph Lauren to Bloomingdale’s, I found what I was looking for at Todd Snyder.

This suit checks all my boxes. It’s solid navy, of course, but made from a cavalry twill wool fabric, which gives it a slightly more interesting texture than your standard worsted wool.

The jacket’s lapels are on the generous side, and come with a preppy three-roll-two button configuration, which is something that I appreciate.

It also features patch pockets! These are a decidedly casual detail, and while they definitely tone down the formality of this suit, to me, that’s a good thing. I wanted a really versatile navy suit, and this casual detail makes the whole thing feel a lot more applicable to casual outfit scenarios. I could very well see myself wearing this in a more laid-back context.

The pants aren’t cut too slim, with a moderately high rise and a pair of single pleats, as well as, interestingly enough, side tab adjusters rather than belt loops.

I’ve never been much of a fan of side-tab adjusters, to be perfectly honest. I don’t outright dislike them, but something about them has always felt perhaps a bit affected and reminiscent of generic European #menswear content that I tend to scroll past without much interest.

I also happen to like wearing a belt or suspenders. I enjoy opportunities to accessorize.

But in the end, I liked everything else about this suit, and so, I’m gonna give the side-tab lifestyle a try. I think they might grow on me, who knows?

All in all, I’m very excited about this suit. Todd Snyder has been riding some pretty high waves these last couple of years, with their fashion week presence and overall acclaim in the industry practically exploding. I’m a big fan of the brand, I will say. I don’t know if the value is completely there, especially with how the cost of everything has gone up lately, but the stuff is certainly good. And this suit? Pretty damn good.

But wait! There’s more to this section. With temperatures cooling and some drafty chills already here, it’s time to break out some cozy sweaters. Over the last couple of months, I picked up a few new knitwear items that I wanted to share!

First up is this maroon lambswool crewneck by J.Crew. I got it off Depop for like $10 and the cable-knit detailing really gives it a little extra something. It’s not too thick either, so it’ll be really great for layering this season. Hype!

Next, I have this vintage Lord & Taylor Men’s Shop wool vest in a delightful shade of forest green. Also with cable-knit detailing! I do love a sweater vest, especially under a tweed or corduroy jacket. This one was a Goodwill find!

Lastly, I scored this classic Irish Aran knit (aka an Irish fisherman’s sweater) at a local thrift store earlier this week. I actually already have one that’s very similar, which I got last winter, but this new one fit too well at too good a price for me not to purchase.

The new one

These things are CHUNKY. Like, really, really beefy. They can’t really be worn under a jacket, but they do look great under an overcoat or trench!

My other Irish knit, last winter

I’ll have to decide if I want to keep both or sell one. But for now, it’s cool to have two in my arsenal.

Last up for this category, I have an all-time grail for which I’ve been actively searching for a couple of years now. That would be my vintage L.L. Bean Flying Tiger leather jacket, recently acquired off eBay for under $150.

A while back, I’d seen a couple of creators in the menswear space tout the value of this jacket. Made in the 90s, in the USA, it offers a sleek fit for a great secondhand price, with options frequently available on eBay for about $100-$150.

I was just struggling to find my size. I’m a jacket size 36, and most listings I would come across were far too large. Then, I happened upon this one. It’s actually a size 34! A truly rare small men’s size. Rarer than mine! But after reviewing the measurements, I realized it would work well for my proportions.

And since getting it a couple of months ago, I’ve been wearing it a ton. I love how it looks with these herringbone wool pants (vintage GAP, believe it or not) and a necktie.

What a fun look! And a spectacular jacket.

Well Worn: My Big Red Barn Coat and 90’s Calvin Klein Jeans

In the early summer, I stopped by Alfargo’s marketplace, a bi-monthly menswear gathering/convention and flea market here in NYC. Normally, I just spend my time there talking with friends and meeting some menswear mutuals, but this instance, I left with something pretty sweet.

I couldn’t help but take home this lovely red barn jacket.

I’ve been wanting one just like this for a while. A quintessentially classic, 90s-coded piece, many of the vintage options I’ve seen online are from staple brands like Eddie Bauer, J.Crew, Land’s End, etc.

Interestingly enough, this one is a women’s jacket (ironically being sold at an exclusively menswear market), as indicated by the buttons being on the wearer’s left side as opposed to the right. It’s from the now-defunct classic catalog brand Carroll Reed, and features a supple, soft leather collar that’s fully detachable, as well as a lovely plaid lining.

It’s a bit large on me, but that’s kind of why I was so drawn to it. Barn jackets are meant to be a bit roomier, and this one is in all the right places, providing ample room for creative layering to suit a variety of conditions. The sleeves fit me perfectly, and the length hits just where I want it to – fully covering the seat and the upper thigh.

The splash of red it lends to my outfits isn’t quite a primary shade, which keeps things colorful yet muted and grounded. Oh, and the pocket space is spectacular. Ample room for trinkets! I’ve been wearing it as often as I can, and it’s quickly become a well-worn favorite.

In fact, I’m actually wearing it today as I finish up this blog post, with the other item I wanted to feature in this section: my 90s Calvin Klein Easy Fit jeans.

I’ve had these for a couple of years now, and they’re some of my favorite jeans ever, quite simply. They’re in a classic, light stonewash and are made in the USA from 100% cotton.

Not only that, but they have the perfect rise I can ask for from a pair of jeans. They hit just right on my waist, and flatter even the flattest of asses (I speak from experience). The fit is a very classic straight cut, with no tapering to speak of, but hardly the widest leg either. Though I love a pair of truly baggy jeans, a true straight cut is arguably the most timeless and classic.

Yet, these still feel so 90s. And I had to show them some much-deserved appreciation here.

And with that, this Watch & Wear is concluded! Once again, sorry for the prolonged gap between posts. I hope that the content here has more than made up for that absence, and I plan to continue posting here regularly. Thanks for reading!

2 responses to “Watch & Wear: Fall 2025”

  1. G.M. Style Avatar
    G.M. Style

    He has returned! Always love reading through your articles man, makes my over-analysis of my own outfits feel just that bit more sane. I’ve been holding onto a black cashmere (100% unfortunately but what ya gonna do) overcoat of my own since last summer and started taking it out recently as the temperatures drop. Very brooding for sure, very ‘I am Justice, I am the Night.’ And your use of red to compliment both earth tones and grey’s has definitely sparked some ideas for my own stuff! Hope you continue to pay that fee for the blog, don’t let the flame die out!

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    1. sullyspires Avatar
      sullyspires

      Glad you enjoyed! Sounds like you’ve got a killer coat there too! And dw lol, the blog isn’t going anywhere. Hope to get something new up again soon 🙂

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