We have entered the era of the personality hat

So, what makes one good, what does it do for your outfit and most important: how should you wear it?

I guess we could have assumed personality hats were going to come in hot as recently as last winter when The Row dropped their flexible pillbox, the Asrid.

The one at far left is actually called ‘Aeria’ (here is a good one from Etsy)

And if you consider how much popularity the fashion baseball cap has accrued in the last decade and follow that up with the riskier winter choice (see: the balaclava) that was first heralded by Raf Simons for Calvin Klein (Fall 2019) —

Is it the one that got away?

— but unanimously embraced by participants of the style zeitgeist, it makes sense that the wave would reach the fantastical echelon of high fashion it’s anchoring into now.

If this is all news to you, I offer a brief visual summary of the last year in fashion:

Two Penelope hats from The Row book-ending a spring 2024 runway look from Prada and a Fall 2023 runway look for Maison Margiela

From left: Jil Sander, Armani, Missoni, Loro Piana, Saint Laurent and Dior (see also)— all fall 2024

And an even more brief definition of what constitutes a personality hat: it is basically any topper that has the power to transform your outfit into something more delectable.

What is it about the personality hat that feels so right these days? I ask in particular because hats have gravitas, you know? When you’re wearing a hat, you’re Wearing a Hat. Making a statement. Projecting a persona. One that does not mince around its message, commanding the room it walks into, calling every eyeball to it.

But what wearing a hat can say about you completely depends on the hat.

A baseball cap says calm, cool, casual, collected —

Polo Ralph Lauren cap, Khaite jean jacket (this one’s less of a jean jacket, but a good bridge to carry you through summer), Daily Blues jeans (like these too), Gucci platforms and double bag from a combo of Etsy (straw) and Clare V. (she’s nice too, if you’re after a lady vibe). Here’s the cap in green, and here are good cat eye sunglasses (these for more flavor)

This is more cool calm casual collected, no? Although the other way you can do this is…

Yali hat, Kule t-shirt (my new fav - the neckline is great), Rosie Assoulin suspender dress (here’s one on TRR, the band goes under your boobs tho), Mansur Gavriel boots, Chylak purse

1, 2, 3 great Etsy picks before what’s in the collage. Now: Polo hat, Jacquemus hat, DSquared hat, another from Polo (here’s the red) and Acne

While something more like The Row’s Penelope will be like, “I am conceptual and understand art.”

Anine Bing dress, The Row’s Penelope hat, The Row white mules (hard recommend — have been wearing like cray cray)

A good alt to this hat is Amy Downs’ “knot hat”

Red tissue turtleneck, blue button down (would you invest in the Charvet one?), My Dear Tejas yellow leather fringe jacket (a blazer like this works too), Old Celine pants, Doen sandals

Some freaky deaky, but not completely impossible wildcards, starting with an embellished cowboy hat from Maison Michel (alternatively priced option here), Gigi Burris’ felt cowboy hat, followed by her ‘Sharina’ hat, then there is the purple number from Maison Michel (on sale), and its embellished companion with a little more fanfare. To top us off, The Row’s ‘Indo’ in nylon for $310.

A pillbox reflects respect for old house tradition, no matter how you plan to wear it: