How Pillbox Hats Changed My Life (And A Few Tips For Wearing One)

The day I found my first pillbox, I set it on top of my head and felt like a new vintage goddess.
Publish date:
December 27, 2012
vintage, hats, pillbox hats

Historically, the pillbox shape of a hat was first used in military attire -- but, of course, later it became the iconic fashion statement we all know and love. I’m here today to share with you my passion for this bold and beloved vintage hat.

Sure, Jackie O could get away with just about any hat you threw on her head, but I’ve always had a large noggin, so most vintage hats can barely get past the top of my head. The day I found my first pillbox, specifically the green one above, I set it on top my head, scrutinizing the vintage find.

“No,” I thought, “This feels all wrong.”

Something about wearing it straight on, in the middle of my head felt too literal. I cocked it to the side and suddenly, we were in business! I felt like a new vintage goddess.

A few years ago, I started dating my current boyfriend. For our first Christmas as a couple, he got me the nicest present a boy could buy. He scoured his hometown for the perfect leopard-skin pillbox hat. Honestly, it freaked me out a little. The gift was too good! Boys buying accessories is a rarity and to find such an amazing vintage piece -- I realized that he not only knew me, but knew my style. What a keeper!

Whenever I wear that hat, I feel like a confident woman who can accomplish anything. I can’t explain it, but when I'm strutting down the street, I hold my head up just a little bit higher. Regardless of the rest of my look, wearing something so bold makes me feel like a bolder person.

When I listen to Bob Dylan sing, "Yes, I see you got your brand new leopard-skin pill-box hat/Well, you must tell me, baby/How your head feels under somethin' like that?” I can honestly reply, “Damn good, sir!”

Pillbox hats are an important accessory in my life for a variety of reasons. They make me feel good, make me stand out in a crowd and they give me the power of self-expression by turning a simple look into something fun and different. I’m the kind of girl who loves to push the fashion envelope, but I’m also kind of lazy and I like to be comfortable. Hats let me dress up without feeling overdressed.

I also love the fact that others seem to find joy in the pillboxes, from the older women I see look up at my hat and smile to the waitress who compliments me and says that she’s “glad they’re still around.” These hats tell a story and I love giving them new life.

Along with giving me a new-found sassiness and joy, the pillbox has also solved the bad hair day problem. Whenever my hair feels frizzy, flat or just plain bleh, my trusty hats are there to brighten my look. I neatly pull my hair back in a low ponytail, spritz some hairspray and adorn my head with a pillbox creation. Voila, a new day!

I’ve personally never paid over $20 for a hat, but I’ve been lucky in my search. I’ve seen hats for over $100 depending on the detail. I can appreciate and understand the price for certain vintage items, but as a thrifter, my advice if you’re looking to start a collection of your own is just to keep an eye out. At thrift stores or flea markets, look for any hidden gems in a box of hats or beneath a pile of dresses.

I know not everyone wants to look like a Pan Am stewardess (like I do) so here are a few tips for rocking this bold chapeau: keep your hair simple, pin the hat to the side (bobby-pins usually work fine) and don’t be afraid to tuck any veils or whatnot underneath the hat.

I’d also recommend picking a contrasting color for the rest of your look if you plan on wearing a white or black pillbox. Otherwise it can give off weird, wedding/funeral vibes (unless you’re into that).

Hats have a life and vibe of their own, but they don’t have to dictate your whole look. I might pair a white pillbox with a T-shirt and bright pencil skirt in the summer or a fun sweater and tights in the winter. Either way, I always feel comfy, dressed up and ready to take on the world.

Do you have an accessory that makes you feel special? It doesn’t have to be a collection, just something that makes you feel confident in your own way.