Three Flirty Summer Looks | Cup of Jo

Back in March, when I was just getting back out there after my marriage ended, I shared two first-date outfits…

Here they are. For those very early dates, I wanted to dress casually and maybe hold back a little? Everything felt new and scary to me. But sweet readers pushed me to get a little flirtier: “I like black jeans, but maybe with a black blouse… you can undo an extra button if a sexier vibe is in the air.” Added MDB: “The black one looks like a server’s outfit.” Haha, noted.

Since then, though, I’ve taken that advice to heart. After going on dates with some handsome gentlemen, and seeing how kind and open people are (especially at this age I find), I’ve felt myself soften and warm to the idea of being more vulnerable — and thus a little braver when it comes to outfits that show that I care and tried. (Does that make sense? It makes sense in my head.)

For a recent drinks date, I wore a polka dot number with Chloé flats that I’d found on eBay. (Dancing arm courtesy of Anton.)

When I had dinner with a cute dad at Sailor, I paired a short skirt with a white blouse (similar here and here) and strappy sandals.

And at the top of this post — on an evening walk — I was wearing a Levi’s jean skirt I’ve had for a decade (!), an old floral shirt, and brown sandals from Poshmark.

Fashion can sometimes feel frivolous and extraneous, but other times it really reflects our emotional temperature, headspace, life stage, all of that, don’t you think? It reminds me of interviews we’ve done with costume designers from Girls and Fleabag — and how characters’ clothes can reveal what they’re thinking and feeling. Not all the time, but sometimes! Claire! It’s French!

Now, I’m so curious: What do you wear to dinners or walks or movies? What makes you feel like yourself? I would love to hear.

P.S. The best sneakers for long walks, and a recap of my very first date after divorce on Big Salad.

39 COMMENTS