SWOON Style Session: Water boots + The Idiosyncratic Aesthete
The art of contradiction, and fumbling around in my closet in the dark (literally) to play with styling water boots for spring.
Lately, I’ve realized that getting dressed has become an extension of self-possession.
An opportunity to play.
I used to shop from a place of “I like this, I’ll buy it.”
Now? I can like—even love—something and still know it’s not actually wearable for me. Not because it isn’t beautiful, but because it doesn’t fit my life. Or the rhythms of my day.
And more and more, I’ve noticed how many women I know are approaching style as a kind of personal language. Something fluid, intuitive, and unapologetic. Not just about what looks good, but about what feels like them.
A kind of sartorial self-trust.
We let the trends inform us—but they’re not the rulebook anymore.
We know what we like.
We’re figuring out who we are, and letting our clothes reflect that back to us.
Maybe that’s why I’ve been really admiring the Idiosyncratic Aesthete—someone who dresses by instinct, not instruction.
Someone who finds joy in a little bit of friction: structure and softness, old and new, polished and a little undone.
There’s something freeing about wearing things that “shouldn’t” work together.
Thrifted pieces with something new. An unexpected layer. The wrong shoe.
And for me, always—a flea market purse.
I’ve been letting myself play more lately.
Because playing in your clothes really is a muscle.
The more you mix and layer and try things—especially the things that feel a little weird—the more you start to recognize what actually feels like you.
The other day, we lost electricity in a wind storm. I was digging through my closet with my phone flashlight, just trying to find something practical to wear—and somewhere in that half-functioning moment, I gave myself permission to play.
There was this one piece I’d always treated as purely utilitarian—practical, not expressive.
But standing there in the dark, I saw it differently.
And I tried it a new way.
After borrowing my sister’s boots for a muddy traipse through Hampstead Heath, I realized two things:
A good pair of boots is a spring essential.
I was never giving them back.
Eventually, I found my own.
They felt sturdy and effortless—something I could wear in the rain or on a whim.
Since that day, my H2O leather boots have become a sort of anchor in my spring wardrobe.
Adding a layer of utilitarian quirk to whatever I put on.
I’ve played with them a few different ways—to see how they move through spring with me.
Sometimes it’s about practicality (hello, rainy days), but sometimes it’s just about contrast. A little offbeat styling that makes an outfit feel like it has a story.
That’s what I mean when I say Idiosyncratic Aesthete—someone who dresses with a little sense of mischief and meaning. Just to be fully them.
Here’s how I’ve been wearing the boots lately:
(Apologies for the screenshots from videos. If SWOON Styling Sessions becomes a recurring thing (big if, very TBD), maybe I’ll take real photos with an actual camera. Or maybe we’ll just lean into the energy of low-res documentation. Perfection isn’t the point. We’re here to play dress-up in the dark.)
Denim Bermudas + Blazer
I’ve been reaching for this more than I expected. The wrong shoe with the wrong bottom for the right jacket—which is kind of why it works. It pushes against the obvious, and I like that.
Satin Maxi + Worn-In Tank
The boots rough up the softness in just the right way, and they add weight to an otherwise light outfit.
Very Important (to me) Thunder Tee + Slip Skirt
The Thunder clinched their playoff spot, and I basically haven’t taken this tee off since. There’s something about sports merch with something delicate that just… does it for me. The boots keep it from leaning too far in either direction. Also—tiny styling note, but sleeves matter. Pushed up, rolled, slightly undone… they can add just enough shape or softness. A little effort that reads like instinct.
Sheer Lace Skirt + Tee + Technical Hooded Parka
The boots give it weight. Keep it grounded. Less costume-y, more character.
Back to the Bermudas (Layered Up)
On chillier days or days I’m trying to cover up my most recent vein surgery, I throw on tights–which I didn't here, an estate sale men’s silk and cashmere sweater, a silk bandana, and the boots. A little off-kilter. A little old-world. Feels just right.
At some point, the boots stopped being a choice and just became the thing that holds everything together.
They don’t make the outfit, but they sure felt good to wear.
Which feels like the real joy of dressing lately—not the perfect look, but the small decisions that shift how you feel in your clothes.
Because the more you play, the more you pay attention, the more you start to see your clothes not just as something you put on—but as something that can have a perspective.
A little truth. A little tension. A little story you’re still in the middle of telling.
Sincerely,
Jessica