I Never Wear Dresses—But for These Spring Picks, I'm Making an Exception

The recent heatwave in Los Angeles has forced me to consider other ways to keep cool in these excruciating temperatures. I’ve never been a fan of dry, sweltering heat, and finding things to wear has become a chore. Dresses have always felt to me like a cheat code; you barely have to think about styling at all, which is not what I’m used to. Still, summer dressing has never been my strong suit—winter is my favorite season; there are just more pieces to work with—so I’ve decided to give in to dresses. Why not show a little leg? I did just turn 30, after all. I’m entering a new era of dressing, one that’s a bit more playful, and definitely sexier.

I am always keeping a keen eye on whatever is going on at J.Crew, especially since Olympia Gayot’s creative is getting better and better with time. She just tapped Camilla Nickerson to style Betsy Gaghan for their latest collaboration with Lee Jeans. From their newest collection I chose this dress made from Liberty fabric, which I’ll be wearing out to dinner this week with a little Prada sandal. I’d also choose this skirt and style it with a ruffly blouse for nighttime or a white t-shirt for day with a nice pair of flats. It reminds me a lot of late '90s Miu Miu.

There is somehow a massive gap in my wardrobe for a classic black slip dress. I’m not sure how this is possible, considering I am who I am, but alas, we are here. I just bought this one from Silk Laundry following a suggestion from my friend as we fanned ourselves with menus sitting outside at dinner last week. I also love the cut of this one from Araks—the sky-blue color is on my wishlist.

Similarly, my close and personal friend Brooke Callahan just collaborated with Hai, meshing Brooke’s classic tie styles with Hai’s gorgeous silks. The pink bow dress is my ideal for a hot summer night in Hollywood. I am endlessly impressed by Brooke’s creativity and am so pleased she and Tessa Vermeulen, who calls herself a “silk merchant," had a meeting of the minds. "We approach design similarly, both very fabric-first while prioritizing simple silhouettes and easy, classic dressing," Brooke told me. Another darling slip skirt is here—we can file this under Toothpaste Dressing, a phrase I just heard last week after a lot of this mint green color was seen on runways last month.

Like a slip dress, you can’t really ever go wrong with any dress from Issey Miyake’s Pleats Please. I have one in my closet that's similar to this, but this season I’m opting for the sleeveless style. This Kallmeyer would be perfect for a chilly evening in Nantucket in June, or anywhere on the Eastern seaboard for that matter. I would not recommend for humidity, however.

I usually tend towards black, but this white silk dress from Dôen is beautiful. I have a few friends who are brides this year and this dress would be perfect for any events surrounding the big day. For me, though, I’m going to show up to the wedding in sequins and a cape. I adore Toteme’s take on the '90s black slip dress, very Carolyn!

I have been incredibly romanced by T-strap sandals. I think they pair perfectly with a dress that can be labeled as plain—any of Emme Parsons' street tappers would do—but my pick are these or these. You can never go wrong with a Martinano kitten heel, either. Any dress with a fishtail screams summer mermaid, especially this Connor Ives piece, whose name has been pleasantly in my ear ever since his runway show last month. Tish Weinstock on the runway makes an A+ show! This beautiful caftan from Tory Burch is perfect if you have a convertible and are planning on driving an hour west to the ocean.

For my 30th birthday I wore a vintage Alberta Ferretti silk dress. I think it’s my favorite I’ve ever worn. Some of my favorite dresses are on TheRealReal right now, like this Michael Kors Celine, some early aughts Dries, and '90s Ralph Lauren.

Speaking of vintage, I popped into Felt Showroom last week to try on some of their pieces, including a handful of Nicolas Ghesquièreera Balenciaga dresses. I never imagined myself as a Balenciaga girl, but co-founder Claire Wickster convinced me otherwise with a draped, drop-waist dress from 2006. Wickser and Yelena Akopian founded Felt two years ago, and just four months ago brought everything together into a bright, beautiful space near downtown LA. My favorite piece I tried on was a Céline by Phoebe Philo blouse—something I’d typically pair with vintage denim, though it would also look great tucked into this Rachel Comey skirt.