Ever Wonder How to Dress for a Hot, Humid Day When You Still Want to Look Put-Together?
How I styled one outfit for a full day of city walking and a night at the theater.
There’s a certain kind of day many of you know well: the kind where you’ll be walking for miles — in the heat, in the humidity — but still need to look pulled together. Maybe you have a full day planned in the city, ending with dinner at a great restaurant or a night at the theater.
Ever wonder what to wear on a day like that?
I recently found myself facing exactly that question during a trip to Chicago. The plan: miles of urban wandering down Lake Shore Drive, dinner at Acanto, and — the highlight — watching Heather Headley perform at the Symphony. I wouldn’t have missed it for the world. Heather’s voice has been a powerful thread in my life since I first heard her in Aida over 20 years ago — a voice that has given me courage in more ways than I can count.
And when it came to what to wear, here’s what I chose — pieces that felt effortless, elevated, and could move with me through a long, hot, beautiful day in the city:
The Jones Ribbed Tank (in a stripe):
Our best-selling foundation piece for a reason. Lightweight with just the right amount of shape — soft, breathable, and structured enough to make me feel pulled together without feeling fussy. (Shape does matter when you want to feel confident all day long.)
The Poplin Prairie Skirt by Sanctuary:
On hot days, I gravitate toward easy, airy skirts — especially when I want a little more coverage without sacrificing comfort. This one has a fitted waist but flows away from the body — no clinging, no sticking — just movement and airiness. Exactly what you want on a humid summer day. And can we talk about the pockets? I actually kept my phone in one while walking around the city — so practical. Plus, there’s something about a skirt with pockets that instantly gives a more relaxed, effortless feel to the whole look, which I love.
Patent Arizona Sandal by Birkenstock:
The comfort of a Birkenstock, but with a little more polish. The shiny patent finish and bold gold-tone buckle elevate the entire look, making it feel right for stepping into a nice restaurant or the theater and comfortable enough to walk miles on Lake Shore Drive.
A simple, long statement heart necklace pulls everything together and adds just the right amount of personality and polish without making the outfit feel fussy
The takeaway?
When you build your outfit with pieces that balance comfort, movement, and polish, you give yourself freedom. Freedom to wander. Freedom to sit front-row and soak in a powerful performance. Freedom to move through a full day without second-guessing how you feel.
I hope this gives you some ideas for the next time you’re facing one of those full, hot, humid days where you still want to show up — fully yourself, fully ready.
Because style is more than what you wear—it’s how you live in it.
With love,
Megan Tamte