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Gapxgq Thehill Side Knolling

Gap x GQ x EVERYBODY, and then this normal blog post devolves into me sharing my crazy personal style theory and confessing my shameful secret desire to wear hats

Gap’s fall collaboration is with GQ’s ‘Best New Menswear Designers in America’ – The Hill-Side, David Hart, NSF, and Stampd. I particularly love everything in The Hill-Side’s capsule collection (pictured above), but I’m also into David Hart’s midcentury-casual vibe (apparently we don’t say ‘Mad Men’ inspired anymore, it’s just ‘midcentury’ now) (below).


Side note: my one complaint is that the windowpane print wool pants in the bottom-left of the above picture don’t seem to have made it onto the website! They can’t be sold out already, so hopefully they’ll be added later. Gap, hear my plea – I need those pants.

There’s an awesome wool fedora in the collection, which reminded me of this theory I have. It’s really unformed so I’m a little nervous to share it – bear with me.

The idea is that people are always growing and changing, so one’s personal style is always growing and changing. But it’s not straightforward or progressive as the word ‘growing’ might imply. It’s an organic and messy lifelong process so always evolving maybe a better word for it.

Me, dressed like a grown-up but not fooling anyone

If that’s the case than I think it can be helpful to set ‘goals’ for one’s personal style. Not for other people, but determining for oneself “I want to wear _____.”

Recently I’ve been trying to wear more of what gets described as ‘Trad’ or ‘Ivy’ clothing – blazers, OCBDs (Oxford Cloth Button Downs – I’m still learning the lingo), knit ties and pocket squares. I like it because it implies a simultaneous ease and stability – two qualities that don’t come naturally to me at all. A tweed blazer becomes both a statement of intent and a sort of armor, helping me feel like the person I’m trying to become.

That’s all a bit heady, and I can’t imagine most people need to think it to death like I do. But implied in that “I want to wear…” is “I wish I was the sort of person who wore…” – the desire to be the sort of person who can pull of that thing.

Gap x The Hill-Side wool fedora

The Hill-Side’s wool fedora – my style Mt. Everest

My current thing? Hats. I think that wool felt fedora by The Hill-Side (pictured in the very top picture, and to the right) is way cool. I have a black pork pie hat sitting in my closet. I know what you’re thinking, but NOT like Walter White’s, more like a fedora, much softer lines. Trivia: Buster Keaton first popularized the pork pie in the US – he couldn’t buy them in stores so he constructed his own by modifying fedoras. He estimated he made thousands of them.

Anyway, mine is without a doubt a nice hat, but I’ve never worn it. Every time I put it on it feels costumey. If I can’t muster the gravitas to take myself seriously when I’m wearing it, how can I expect other people to?

I don’t even know what it means, this desire to wear a hat. Does it have to do with recovering a formality and civility in social interaction? Hats feel kinda formal to me, and I do love anachronism. But you can’t be reductive about these things, and you have to trust your instincts – whatever the hat means*, I want to go to there.

So I keep trying, and one day I will get there – I’ll find the right combination of ensemble, event, mood. Then I’ll find it again, and before you know it it’ll stop being a novelty. Who knows where it goes from there… Single-handedly bringing back the practice of wearing hats? Somebody’s got to do it.

Have you ever set a goal for your personal style? Worn something you wouldn’t have imagined yourself wearing a few years prior? Worn something daring and had it fall flat? I want to hear ALL the details, or if I’m crazy someone ought to tell me that, y’know, for my own benefit.

Adventurously yours,

* As I recall there’s a whole book about men’s hats somewhere in my stack of books to read – Hatless Jack