How many shackets is too many?

Or, initial thoughts on how to dress as a midlife man

Can a man have too many shackets? I have four and I suspect people are starting to notice. I figure I can wear one of my beloved shackets twice a week, so I rotate all of them on a two-week cycle. With caution and attention to my audience (office, remote work, different social settings) I might get away with wearing a shacket every single day. While they are all different enough (2x corduroy, 2x flannel, one reddish, one green, one tan, one black and white), there is no mistaking the tell-tale boxy profile and faux lambswool lining – people know what I’m after.

I would like another, but I think that may be overdoing it.

What’s a Shacket?

Obviously a cross between a shirt and a jacket. You’ll need an undershirt for sure. They tend to be heavier than a thick flannel but light enough that no one will dare ask you if you’re planning to ‘stay for awhile’. AKA shirt-jacket or overshirt. Around since at least the 1940’s, and much more popular the last 10 years or so.

The shacket is an incredibly versatile piece of clothing. From both a weather and a vibes perspective.

With proper layering, one can sport a shacket for approximately eight months of the year (including the cooler days and evenings of those shoulder months, September and April). If you wear one in August or May you’re just being ridiculous. Other than jeans, name me a single piece of clothing so relevant. Here are some pics of guys looking awesome in shackets:

But what makes shackets so special is not just how cozy they make you feel every single time you put one on (after all a lightweight patagonia puffer accomplishes the same). The reason I’m reaching for a shacket on so many mornings that I know I’m gonna look not just good, but that I’m going to look with it. Which is a priority as a 44 yr old suburban male.

I contend that a shacket is the ultimate shortcut to looking fashionable as a middle-aged man. You can keep everything else the same: boots/sneaks + jeans of any shape/color + t-shirt… if you add a shacket to the equation it just upgrades the whole thing. If my shackets could speak they would say not only “come what may, I will be comfortable” but also “I’m still trying. I will not settle for a sweatshirt. I am still in this game, damnit.”

Which gets at one of the crucial questions of midlife: how hard should I try? If one of the tasks of midlife is to graciously accept the death of our youthful ego projects, to what extent should we expend energy to keep looking cool?

It can be downright pathetic when the dad of teenagers chases the latest trends, attempting to “forestall the appointments with the inherent self”, as James Hollis says. This is Kevin Spacey’s leather jacket in American Beauty. Or for you Updike fans, Rabbit Angstrom:

He wears the same jeans he used to wear when he was younger, but they don’t fit the way they used to. They are tight around the waist, and the fabric is faded and worn. He looks in the mirror and sees a man trying to hold on to something that’s slipping away from him. He wishes he could still be the young man who ran fast, who felt invincible.

Sad! Or take Danny and his ‘lucky boots’ from Jennifer Egan’s novel The Keep, “He thought: I'm a guy who wears boots like this. It was the first thing he knew about himself.” Pity the man who gets his sense of self from his shoes. And? I get it. We’ve all been there. But to see this dynamic from the outside (via movies or books or whatever) is to be granted power to see ourselves, to be inoculated so that next time we’re tempted by the perfect jacket we can remind ourselves that no jacket can slow the inexorable passage of time.

Sidebar: When is it appropriate to wear really bold clothing choices as a midlife man?

There are obviously dudes in their 40s-50s+ who dress with boldness. How do they get away with it? IMO there are tw acceptable cases:

1/ Passion for the fashion: going deep on a topic is cool. It’s super cool to care enough about something that you spend time learning, sharing insights in a community, curating a personal perspective. Fully supportive of fashion as hobby.

2/ Part of the job: if you’re rockstar you can dress like one.

So we have established that one can be way too obsessed with what to wear. But does it mean we just…give up? No! We need to accept our new limitations while holding on loosely, and with grace to our fading youth. After all midlife is a liminal season, and the shacket is nothing if not the ultimately liminal (in between, transitional) item of clothing.

Our energy flags and we don’t or shouldn’t care quite as much what people think, but we still want to appear attractive to our lovers, and to do our part to elevate the visual quotient of the universe. While we need not rage against the dying of our light, we can speak up and demand that things take their time, thank you very much.

The shacket strikes the perfect balance: looks just good and cool enough without trying too hard.

However this does create a problem. As we midlife males buy up the available shacket stock it only hastens the shacket sunset, that moment when whatever coolness we had borrowed from sporting our shackets is undermined by the sad reality that middle aged men everywhere are wearing them, and they become inherently uncool. At that point we will need to move on to something else, maybe the shawl cardigan?

But until that day, wear your shackets with confidence and nonchalance.

Any other good examples of perfect liminal clothing items??

Here are some thoughts on selecting your next shacket:

• Profile / structure: don’t let it be mistaken for a heavy shirt. You want something with good boxiness. Especially if you’re skinny like me, big shoulders and a wide profile will make you look like a linebacker (good thing) while ensuring you have ample volume for whatever undershirting the climate dictates

• Texture/material: no wrong answers, but consider flannel vs corduroy vs denim vs other. Corduroy is a little more dressy, while flannel (particularly if in a tartan or plaid pattern) can get you called a lumberjack (bad thing most days).

• Lining: puffy white lining is super cozy, but it really stands out so make sure you don’t overdo it (guilty!). Fleece is also nice. But without a lining it can end up looking like just a shirt (see above).

• Pattern/color: Solids are a bit more formal and better for the office. Plaids and check stand out more, but up the risk of trying too hard. Plus people are more likely to remember them, and then you can’t wear them as often!

• Price: Good news – you do not have to spend a ton on a good shacket. And classic stores like LL Bean do them right and at a high quality.

And a few recommendations:

JCrew, $151

Lands End, on sale for $75

Faherty, on sale for $119

LL Bean $170

Brooklyn Cloth, $46

LL Bean, on sale for $90