I’m Doing It: How to Wear a Straw Hat this Winter

I know what you’re thinking, I’m thinking it too and guess what: I think it’s super weird that I keep forcing summer accessories during winter months on to you also. Between last fall’s call to wear a beach bag through February, this winter’s imminent straw hat (do see above) and between us, I’m wearing espadrilles with camp socks today, it has become severely evident that I will neither let summer go nor winter fully come.

But hear me out — does that have to be a bad thing?

Must I be judged for putting forward a state of mind that can be concretized by the fell swoop of an accessory that will not affect my quest to remain warm? (As in, this hat won’t make better or worse my motivation to avoid hypothermia.)

I just feel like I spend so much time self-medicating by writing about how to get through the winter blues without experiencing that winter blues feeling. Simultaneously, I have practically elected myself the president of enforcing a strict wear-only-what-makes-you-feel-like-the-best-version-of-yourself dresscode policy. So why not officiate the marriage between my presidency and tendency to self-medicate and come up with actionable ways to feel like the best version of yourself throughout the winter blues — right?

One really good way to kick start that program is with the introduction of a panama hat, which I am pretty sure you already own. Mine has painted pineapples on the crown which is practically like the clothing equivalent of an anti-depressant but that doesn’t mean that un-tarnished one won’t work the same magic. Pineapples are not a mandatory accessory in one’s pursuit to feel paradoxically perfect. Paradoxically perfect because: how stunning are both the visual and intellectual concepts of a thick wool scarf and a straw hat? Like meatballs coupled with pasta, it just works. You don’t know why. It just does! So try it using this recipe, would you?

1 summer hat (bucket hats do not apply)

3 parts winter outfit; I would opt for a sweater, wool pants and either a boot or slippers depending on whether you’d like to add an element of grandparental reference

1 tablespoon accessories; for me that meant eccentric optical glasses and a cuff with shit tons of chain hanging from it.

Now spin around three times and ace that drunk line test, ey?

Photographed by Krista Anna Lewis


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  • Natali

    Woman, you’re the coolest chick ever!! Thanks for constantly being so unique, true to yourself and super duper inspiring!! 😀


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  • ReadER451

    You look so comfortable, but also ready to tackle the beach.

  • This style hat would totally fly in chicago… right off my head and into Lake Michigan.

    • Yvonne Dunlevie

      Josie, allow me to research some DIY chin-strap options for you!

      • If they make me look like I have mutton chops, I’m down.

        • Yvonne Dunlevie

          I am only finding things related to sleep apnea….

          • Hahahaha It’s all good. I have my eye on a vintage hat with ear flaps that I might buy and then I may or may not add faux fur to them there flaps.

  • Amanda

    Super practical question: I love extra long wrist decoration like that bracelet, but for real, how do you keep it out of the toilet and the sink? Is it a remove before wiping/washing kind of deal? Or do you have some sort of ninja sleeve tuck trick that keeps you clean and dry?

    • Leandra Medine

      you know, ive been really constipated so this hasn’t come up, but it’s a good question. i think probably just use other hand though if you, like me, are lazy.

  • Ali

    Leandra – Another great article – thank you.

    Question: Since you are pro straw hats and beach bags in winter, was wondering your thoughts on wearing sleeveless dress or tops to the office during the snowy months.

    I do… And get grief from everyone around.

    • Leandra Medine

      I’m doingit! Will send a pic accordingly. Might need 48 hours

    • Krista Anna Lewis

      Not that you asked me, (HI!) but put a tissue turtleneck under it and call it cozy!

    • Leandra Medine

      Cristina from our sales team does it all the time — the heater wants what the heater wants.

  • Julie Meowmeows

    It’s always summer somewhere!

  • Mary Yasmine Arrouche

    A concept I fell in love with when Phoebe Philo did it for Pre-Fall 2013.

  • Lily

    I WANT that Tibi sweater!