Vacation style = freedom = joy
Do you subscribe to Leandra Medine Cohen’s The Cereal Aisle? Recently she was talking about the recipe for WTW if you’re likely to bump into an ex. One part of her formula asks: “What is a style risk you have recently taken that actually paid off?” And she unpacks it like this:
“What is a style risk? That thing where you put something on in private, which makes you feel like, “damn this is good!” The risk element is your not being sure whether you’re confident enough to wear it out, but taking it for a spin in the public square anyway. How do you know if it has paid off? When you think you’ve succeeded to add a new layer of depth to the shape of your style, or in other words, when you say to yourself, “I’d totally do that again.” This, in my view, is how to build fashion confidence: through the trial and error of taking small style risks. Often they don’t work, which can be kind of deflating, but on the bright side, “it’s just fashion,” so keep iterating until they do.”
In my everyday style, I am most frequently in search of no-risk dressing. I love style, but have no time to waste; usually I have 25 minutes to get ready. So I rely heavily on things I know work. When I find something that does, I often search out repeats. I loved a suit and Converse x Comme des Garcons sneakers one day. It just worked. And so I find myself looking for the next suit. Another pair of sneakers with a twist (hence why I know own Margiela Tabi sneakers).
But the sneaker-and-suit look itself is the work of a style risk by someone else; I’ve just jumped on their back. Someone out there first dared to try sneakers and a suit. First said — “Yes, it’s ‘wrong’ but it’s so right. And I am leaving the house.” And someone saw that person in that look and knew: This is good. And that became part of the public consciousness and came to me on the raft of … instagram in all likelihood (sometimes I remember the moments, shoot them and plan to replicate them in some way; sometimes it’s less conscious).
If everyone were like me — just replicating a formula — where would we get the freshness?
I love all things Trinny Woodall. But my latest love are her insta stories on weekends, generally Sunday, where she starts just trying things on in her closet and experimenting and discovering. She’ll look at the way she always wears something and wear it in a different way, layering risk upon risk. That leopard x leopard look? Swapping the white T for a neon shirt makes the payoff even sweeter. So what stops me from de-coupling my own clothes, pulling apart my tried-and-true pairings and just going for it?
I realized recently that I do this on vacation. And I’ve figured out why:
Access to a more limited amount of items inspires me to do more with what a have. (Part of the very principles behind The Flair Index’s The Wardrobe Project, a sustainability and consciousness-driven wardrobe edit process that starts with creating your “ultimate packing list.” ) That one dress I packed? Shove on a sneaker; now it’s casual. Layer on the necklaces I picked up at a local market and it’s good for dinner at the slightly more upscale spot.
That vacation sense of escapism and looseness seeps into my willingness to try new things. Over my binding waistbands? Why not go out with a belt loosely tied around my husband’s shirt? Grab a Dopp kit when I can’t find my handbag for our morning coffee? Why not?
Being away from home, meetings, and anyone I know somehow makes it feel there’s nothing at stake, and I can leave the house in whatever without judgement, including my own. I’m seeing people I’ll never see again. I can try out a whole new style persona if I want to.
Changing, unexpected climates mean creative layering. Throw a vest over it, try the sweater under, etc.
Vacations have that “make the most of it” spontaneity that doesn’t allow time to second guess yourself, you have to keep it loose + just go to make the most of the moment. Tuck untuck. Necklace no necklace. There’s no time for doubt when the last seating is at 8.
You change more on vacation! Post swim, showering at different hours, etc. etc…More opportunities for trial just arise naturally.
Actually, one of my new vacation traditions on road trips (where it’s ok to toss in extra items) is packing some things I’m *not* wearing at home. Either I’ll make them work in ways I never dreamed (the weird Zara dress mistake looks sharp open over denim as a duster) or I donate them from the road.
I look at this snap above and it’s exactly all of that. We randomly decided to venture out to a nicer restaurant than our usual sandwich shack. All I had for “nice shoes” were these Toteme thongs. It was hot, so I needed to keep it light. My (used via The Real Real) Marni shirt was a very light cotton. I hadn’t even worn it before, but now I didn’t have time to think about whether I liked it or not! Or whether I should belt the white Brunello Cucinelli pants (bought used, also unworn). I wouldn’t normally put a maroon bag with any of it, but the maroon version of this was all I had here. I started with one yellow necklace for a color pop and I wasn’t sure, so I tried adding a second. And then it was time to go. I was happy with this (you can tell). I just liked the different colors, and I was glad to be in the pajama style shirt. It’s why I took a picture before we ran out.
But it makes me wonder — what am I so afraid of at home? I do sometimes take some time, like Trinny, to put looks together on a weekend. But I do it to save time later, not to TRY. NEW. THINGS. I still don’t seem to look at pieces in ways other than what I first imagined when I bought them. At 50 I generally feel fearless, so why when it comes to this world that I love, am I so afraid of getting it wrong?
We have some big moves on the horizon, first to this Marion vacation home for the rest of the summer and then to Miami where we just got a place. As long as I’m uprooting myself, I’d love to be able to seize the moment, to pack some vacation rule-breaker spirit and take it with me. After all, as Leandra said: “It’s just fashion.”