Jessie Loves: A Week Of Outfits

A poofy dress, shifts over pants, chic aqua shoes, and a necklace with special meaning.

I promise I do not usually have this many exciting things going on in my life but the last week was jam-packed with events. So many fun occasions to dress for. I thought I would write this letter about the things I’m wearing, how I’m styling them, and what items I’m loving at the moment!

On Tuesday, we had an all-day company-wide meeting where we presented the Resort collection. I chose to wear a lacy top that’s a version of our Poppy dress. I paired it with some favorite La Veste striped pants. I love the color of the pants and the intricate detail of the top and the way they look together. A mash up of so many different details is such a nice styling trick.

I started the day off in my red mesh Landon shoes, but then Amber delivered my personal order of our aqua shoes (which I’ve been dying to wear ever since we designed them a year ago). I opened the box and put them right on. They are so comfy and squishy and fun. I love wearing something a little bit unexpected.

After a long day of meetings, I headed up to Parsons School of Design where my friend Yoon Chang who is a professor there had asked me to meet with her senior students and critique their thesis collections. I was totally blown away. So much talent! Seriously. I was beyond impressed.

The following day, I went to work in my tennis gear, then snuck out for my lesson. I love this Kule trompe l’oeil sweatshirt with this red Wilson tennis skirt. Such a cute, fun combo. I’ve been wearing this tennis outfit on repeat (like I wear it every single week and it’s getting weird).

Then I high tailed it back to the office for a few more meetings before racing over to the west side to board a boat to celebrate the FEED x Minnow collab. Morgan, founder of Minnow, is our neighbor in Charleston and I have known Lauren, FEED’s founder, for years. She is such a lovely person inside and out. The boat was so much fun, bumping into lots of ladies I love catching up with like Dee Poku, Rachelle Hruska, Lydia Fenet and so many more.

For this event I pulled out an old dress from our line, the Gillian (we just released it in gingham for spring). We got the best weather for the boat so I brought along my sunnies and a hair tie (I hate my hair whipping around in the wind). I also wore this new crochet straw tote with our pretty rose motif. This is in the cab as I was racing to the dock and almost missed the boat.

On Friday, I was invited to attend the benefit for the Ali Forney Center by my friend Nikki Kule. I brought one of my favorite friends, Liz Libré of Lewis, as my date. This organization is SUCH an incredible one, serving homeless LGBTQ youth, many of whom have been rejected by their own families. It was an emotional night but also gave me such a boost of hope as hundreds of attendees rose to their feet, clapped, danced and committed themselves to protecting these vital and beautiful fellow humans. Please consider donating!

The dress code was “Queer Elegance“ — “attendees are encouraged to embrace their most authentic and radiant selves.” I thought long and hard about what to wear for this event, and as soon as I saw this Self Portrait dress I knew I had to have it. The polka dots! The shape! The poofy interior crinoline that makes it puff out! I felt like a ballerina in it. I paired it with our new straw clutch and some old brown Margot big bow heels. I loved the way it looked.

The next morning we got up early and drove out to Long Island for the weekend since the weather was going to be gorgeous and I could force my kids to go there because it was Mother’s Day weekend. On Sunday, we had such a lovely meal by the water. I always forget how few clothing items I have out at the house and it’s such a random hodgepodge of things. I truly look half nuts most of the time because I don’t have the right items in my closet there. I found this old Sea dress to wear. The color is dark for me and the dress shape is very different than my usual style but I adore it. There is so much detail and thought put into the placement of the print. I paired the dress with my lovely LR jellies which are sparkly and so, so comfortable.

Back to the office on Monday, I wore my crochet dress which I am obsessed with. I love the trick of wearing a dress over pants. It’s so good during these transitional weather times because it keeps your legs warm and also looks interesting and cool. These pants are the famous Donni ones that I had to buy in one size too small because I love the color. Shown also with my trusty Kule sweater I wear literally every day.

The next day, I wore a really comfy outfit. My green Demi pants and this super cozy sweatshirt. I love a casual, bum-around item that also looks cool! I finished off the look with our Cooper Mary Jane sneakers and my favorite Underwater Weaving basket bag.

I don’t really wear a lot of jewelry but I decided to put on this charm that Brian had made for me probably 18 years ago. It says “La Biondina,” the nickname our first factory in Italy had for me, meaning “the little blonde girl.” So sweet!

At night, I had dinner with my Soup Group and Liz and I basically showed up in the same outfit. She is my biggest LR supporter and it means so much.

Today, as I write this, it is a torrential downpour. I’m in a comfy long sleeve tee, my new fav slouchy jeans from The Only Jane (hi

Jane Herman

!) and our aqua shoes again.

What are you wearing these days? Any styling tricks or fav items you are coveting? Please let me know!

5 Things I’m Loving This Week

1. My son Harry made a little scavenger hunt for me in my office which culminated in this sweet note. I will treasure it always:

2. I am SOOOOO pumped to have this stunning photo by the photographer Johnny Miller. I just picked it up and now need to decide how to have it framed. These are flowers Johnny shot out on Long Island, so it feels extra nice to hang this piece in my bedroom there.

3. I’m obsessed with our new rhinestone flips flops!!! I was lucky enough to bring a prototype with me on vacation this winter and I wore them every single second of the trip — on the beach and out to dinner and everything in between. This pair will 100% be my most-worn this summer.

4. I saw this vintage headboard on Chairish. I really wanted to get it but then chickened out.

5. I’m currently reading Keith McNally’s autobiography and really enjoying it. And I LOVE this stunning vintage book I bought just because of the cover.

And One Thing I Hate

This about sums it up:

Giveaway Winner!

I’ve been writing about style, design, and all my current obsessions since August and ‘Jessie Loves’ just hit 10,000 subscribers this month! This has truly been a labor of love and I couldn’t be more grateful or feel more welcomed by this amazing community. As a little way of saying thank you for following along, I’m excited to send our sold-out Dina totes to one lucky subscriber… and that subscriber is Allison Holmes! Look out for an email from my team.