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[Just a note: Paid subs, please scroll all the way down for a video of my Tibi try-ons.]

I’ve battled with “just wear something casual” my whole life. We can unpack this in therapy. I felt insecure without some sort of a heel from law school in the 90s until Victoria Beckham wore sneakers and I realized how much my feet hurt - in my 40s. For all those decades I also “liked myself” better in skirts and really hated wearing shorts or jeans. Every casual event was a challenge I had to work around - largely to evade judgement: “Ooooh, why are you all dressed up?”

I have written in the past about why I hate “chill.” And recently I revisited this post on the tyranny of effortless dressing (still holds up, though maybe not the haircut).

But as I packed and unpacked and packed again with locations that included the fairly casual (Springs in the Hamptons and Little Compton, Rhode Island), I realized that casual, after all this time, comes naturally to me. Not only that — but I realized that I like it.

Here’s how the whole thing went, and what I learned.

… ok, the Takeaways this week:

Slowly love everything you own, including the “basics”: If even your basics feel like you or just work so beautifully that they become Security Blankets, then transitively, you will have a far better chance of loving even the simpler looks you put together. I first noticed this on a trip to Maine - it was like anything I grabbed, my distressed flannel shirt, whatever, seemed to build a look I liked. (In fact the randomness especially does a lot for casual.)
Lean on your Security Blankets: The pieces you rely on again and again become like talismans of “you”-ness. (Like my Emme Parsons belt with the long tail.) So when you want to feel like you, they are a kind of shorthand.
Develop a casual formula: Observe times when you dress casually and it feels like you. If you repeat the pairing with different pieces, does it still work? You are on your way to a formula. I’ve realized a padded shoulder tee under an oversized button-up is the start of a casual formula for me.
Have a few “casualizers” in your arsenal. One biggie for me is this Emme Parsons belt, which instantly relaxes even dress pants and silky skirts. I have it on a dress as I write this. It’s the color, leather type and extra-long length that makes it such an effective casualizer.
Know your style and do a speed check. At this point it’s coming naturally to me, but it’s a great before-you-leave check. My style is “Miami King.” I need something bold and I need trad “masc” elements. A sweatshirt and jeans won’t cut it. But a padded shoulder sweater with real gestalt, jeans, and shiny loafers with an oversized fringe? That fits the bill.

Want help knowing your style? Have you tried the HMS STYLE GENERATOR?

Aha! A new way to define your personal style.

May 30

Some of you might know that I recently sold my marketing and advertising business to my former partner; I’d been the founder and chief creative officer for over eight years. One of the most frequent things I was called upon to do during that time was lead the development of brand DNAs.

Ok now let’s go get coastal and casual together:

MONDAY

traveling NYC → Hamptons on the Jitney, out to lunch in the Hamptons.

Celine boyfriend jeans (I’m in a 27 here)
Phoebe Philo Tide sandals … I haven’t bought from Anonymous Copenhagen but hear good things … this comp!
Emme Parsons belt
Paul Smith men’s scarf
Saint Laurent Amelia sunglasses (I had these made prescription)
ATM schoolboy tee from my white tank review, at the bottom of this post:

Do we really have to love all our clothes?

October 11, 2025

When I arrived back in Miami after summer in Boston and two weeks in Italy, the first thing I did was an Intuitive Culling, a reaction to being confronted with so many clothes, and specifically so many clothes I just didn’t … want to wear.

Lofted Settledness? Yes. I had more layers on the FREEZING Jitney! I really love that this tissue-thin cotton scarf gives me something without adding heat or formality.

TUESDAY

shopping around Amagansett + East Hampton, including Grandma’s Vintage!

secondhand men’s Gucci tee — if you take your tee plain try this one … and secondhand options here + here + here
Emme Parsons belt
Issey Miyake pants (XS on TRR + another option) … for something more reasonable I like the look of these; I have not tried the brand but have read good reviews and like the philosophy.
Phoebe Philo green flip flops are sold out online (how are there this many insane people?) … Larroude’s option looks good + I have enjoyed their shoes. I actually love these for $25, the color, lines. And love the women-founded brand.
Secondhand Bao Bao bag (options: on sale, secondhand, and if you just think a metallic tote would be handy, this is $33 and it’s adorable)

Lofted Settledness? Yes. Even though the pants might read as dressy on the hanger, this particular belt (vegetable leather and color) and the flip flops are very casualizing.

WEDNESDAY

jitney → train → home to Boston

new (to me) vintage Levi’s jeans from Consistency Project
Roots of Fight Jackie Robinson tee
necklaces, one via Native American elder + one via At Present - this one is great; don’t forget we have a code; HEYMRSSOLOMON15
Hanna Yoo ear cuff
Prada Collapse sneakers cost less here if you know your size (TTS)
secondhand The Row Cowal blazer - runs big so you can get away with a size smaller than your usual. I would do Tibi’s crispy nylon and have the same feeling. This Tibi on TRR? The blazer I’m wearing has cutouts in back so you can tie the sleeves in front, our friend Phyllisa says you could make this yourself.
Emme Parsons belt, glasses as above