I Declare This Winter the Season of the Silly Little Cap Because We Need Joy, Dammit

The Paris Theater is only a six-minute walk from the 57th Street station, but I was already running late and convinced that if I didn’t make it to the theater at exactly 2pm, then I’d miss not only the 50th Anniversary screening of Grey Gardens, but also Julia Fox and Alexis Bittar’s introduction to the cult classic documentary. I decided a little less than halfway through my walk from the subway that I’d just run, which was kind of stupid considering 1.) it was really not that serious to begin with 2.) the plaza next to the theater was wet and 3.) I was wearing a pair of extremely impractical vintage Frye boots. I was also wearing head-to-toe black lace with no bra, just a pair of Los Angeles Apparel micro shorts underneath.

If this all sounds ridiculous, let me remind you: This is New York. I’m the least interesting person at any given place at any given time. What was interesting, though, was that there were at least four to six other frazzled women running beside me, all of them dressed like Grey Gardens’ Little Edie, the iconic first cousin of Jackie O., with their fur coats, slip skirts, kitten heels, American flags, and of course, some kind of interesting headwear. Of all the occasions to debut a statement hat or patterned headscarf, this was the one. Except, in an effort to keep my bangs from puffing up with the unusual humidity we’ve been experiencing this October, I decided to wear my New York City Ballet baseball cap. Little Edie would’ve been so disappointed. That woman knew the power of fun headwear and I failed her.

The reason I say all this is because after watching the documentary on the big screen for the first time, I was enamored by Little Edie’s signature headscarves (which were sometimes towels or sweaters or skirts) and all the interesting hats I saw in the theater, including Fox’s Vaquera Bow Hat. It made me think about the importance of accessorizing — especially in the colder months — and the joy that is the silly little cap.

Before I continue: No, I don’t actually think headscarves are hats/caps, but for the sake of what I’m going to discuss here, I’m including them in my taxonomy of “silly little caps.” And when I say silly, I mean endearing, playful, and somewhat unnecessary but reliably mood-enhancing.

When I saw all of the tiny crochet skullcaps coming out of Copenhagen Fashion Week this year, I knew I was witnessing something special. Like most trends, the crochet skullcaps that are beaded, sequined, and adorned with crystals, seashells, and tassels aren’t anything new. Crochet itself has held an important place in fashion history for decades. As Coveteur pointed out, “women spent a lot of time crocheting hats, scarves, and ear muffs to send to soldiers during both World Wars, and the Cloche hat, often crocheted, was a fad in the ‘20s.” Ali MacGraw famously wore a navy crochet cap to the Oscars in 1971, pairing it with a jeweled choker and a long-sleeve gown. Decades later, it reappeared on Natalie Portman in Léon: The Professional and Stacey Dash in Clueless. In the 2000s, celebrities like Britney Spears and Cameron Diaz revived the trend, pairing their skullcaps with t-shirts or sexy dresses with plunging necklines.

But the crochet skullcap isn’t the only silly little cap you can embrace this fall and winter. The newsboy cap (one of the more controversial trends of the 2000s) has been creeping back into style, recently spotted on Addison Rae, Tyla, and Kendall Jenner. Meanwhile, sailor hats like this one have been appearing on the runway (take Tyler McGillivary’s SS26 show, for example), as well as delicate lace bonnets like the ones seen in Bora Aksu’s SS26 collection. And of course, there’s the headscarf or bandana, secured with a brooch like Little Edie, knotted under the chin like Sabrina Carpenter, or worn over a baseball cap like Timothée Chalamet or Rihanna.

So how do you actually style a silly little cap? Is there a way to wear one without feeling like you’re in costume or worse, “doing too much?” Here are a few tips:

• Commit, commit, commit. The second you tug nervously at your hat, it stops working. Wear it like you mean it. Remember those statement necklaces you wore in college? Treat it like one of those.
• Basics are your best friend. Most likely, you already have a chunky sweater, an oversized blazer, or a tough leather jacket in your closet. A silly little cap is an easy way to add a little more personality and interest to your go-to cold weather uniform without feeling like you’re trying too hard.
• Consider it an upgrade from the baseball cap. Your silly little cap is just as easy to throw on as your MoMA Yankees baseball cap, only it’s better because you won’t look literally like everybody else.
• Play with everything. When the rest of a look is fun, the silly little cap stops screaming for attention. I love the idea of wearing a bright red sailor cap with a leopard coat, a newsboy cap with a ruffled skirt, or a sequin skullcap with a sporty track jacket. What about a romantic veil with a polo and itty bitty shorts?
• Embrace the past. I’m not saying go full Little House on the Prairie with your bonnet unless that’s something you’re into, which, as Jemima Kirke once said, “what the hell, sure.” What I’m saying is, when in doubt, you can always take inspiration from the “it girls” of the past. (See: Françoise Hardy and ABBA’s Agnetha Fältskog.)

And most importantly: channel your inner Little Edie. Seriously, if there’s anything I can recommend, it would be to watch Grey Gardens and take some notes. The point of getting dressed shouldn’t be to look perfect; it should be to express yourself and to bring joy into the everyday, even when things might feel miserable. Little Edie knew that. You should too.