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Jessie Loves · Aug 13, 2026

Jessie Loves: A Summer Wardrobe Exit Interview

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Jessie Randall · Jessie Loves

The words “exit” and “summer” in the same sentence? It’s too much to handle!! Thankfully, we still have a few precious weeks left, but in the meantime, I wrote this retrospective on my summer wardrobe: the biggest lessons learned, the things I wore, those I didn’t, and the styling tricks that made it all work.

Biggest Lesson Learned:

Every summer I have dreams about getting dressed up and wearing fancy things. But one of the biggest takeaways for me this summer is that my wardrobe ends up being far more casual in the end than I realize. Nine times out of ten I was in a slouchy pair of pants instead of a fancy dress. Maybe I wasn’t super social, or maybe I just didn’t really have the occasion to get glammed up. But when I did, I was wearing flats. I even bought the real Chloe jelly mules and basically never wore them.

My Top 10 Most-Worn Items

  1. Baggy butter yellow pants

  2. These sandals in red

  3. These sandals again in dark brown

  4. These t-shirts in white, beige, and off black

  5. These boxer shorts

  6. This long sleeve and this long sleeve too

  7. Cashmere cardigan nearly every day

  8. This cotton set, but mostly the top

  9. White ballet flats (my pedicure is not looking its best most of the time)

  10. This plaid top and this easy eyelet top

Summer Is Colder and Rainier Than I Want to Admit

I have a sort of “glass half full” attitude when it comes to summer weather. I refuse to consider it will be anything but perfect sunshine every single day. In reality, it was wet and chilly a lot of the time. And that air conditioning at the office and on the bus is overzealous. As a result, I wore layering pieces and pants so much more than I would have expected.

In the immortal words of Nora Ephron, I feel bad about my neck. But I do love this raincoat.

Most-Worn Layers

  1. My striped chore coat with the best pockets

  2. Favorite 1960s vintage sweatshirt (good place to find others is Front Street General)

  1. The aforementioned cashmere cardigans tied at the waist or over the shoulders always just in case!

  1. Sadly, a rain coat. I do love this polka dot one

Even When I Dress Up, It’s Low Key

The times I did get glammed up, it wasn’t full-on fancy. I like to have a side of casual with my dressy.

A few distinctive and special items amped up my outfits without being too precious or serious. The wow items that added flair to my outfits include:

  1. My Candy necklace in aqua

  2. This sheer skirt I keep mentioning

  3. These striped trousers

  4. This ruffled wow top

  5. A fun gingham circle skirt

  6. My favorite basket bag

  7. This wacky colored striped skirt

  8. My crochet dress

My Favorite Styling Trick I Tried

One thing I consistently did to add interest to my outfits and nip in my waist was wearing a scarf. I wore this crochet scarf constantly. And I loved cinching in this polka dot scarf.

My Most-Worn Summer Item

If we really are keeping track, it’s probably my tennis tap pants and skirt. I made a promise to myself this summer that I wouldn’t buy more tennis gear. I wanted a uniform and to stick to it every single day. I like how this made getting dressed for the courts easier, and it also defined my tennis look.

Oh, and! These sunglasses I wore literally every single day. They are a bit flashy but I adore them.

The Thing I Get the Most Compliments On

These clogs are fun and nostalgic and people took notice! Also that wacky striped skirt is a compliment magnet.

Vintage Brought Everything Together

I love to add in vintage pieces because they are so special and totally unique. I visited Manhattan Vintage with my friend Nikki last weekend. How gorgeous is Khata Vintage in this vintage slip?

I ended up purchasing this bias cut dress and am excited to wear it over jeans.

Another vintage piece I wore a lot (see: chilly air con and rainy summer) was a vintage college sweatshirt. As soon as my son got into college I ran to Etsy and found a gem. So much better than the new stuff. Highly recommend!

The Best Trick Up My Sleeve

In addition to my love of a dress OVER pants, I also wore my pants OVER my dresses. I tuck light dresses into my pants to make them work double time as a top.

What was the item you wore the absolute most this summer? Please tell me because you know I am always on the hunt.

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Five Things I’m Loving This Week

  1. Seeing the way people wear LR. I often get asked who I get most excited about seeing wearing our collection. And for me, it’s never celebrities, I could honestly care less. What I love is to see friends, or peers or random people out on the street in our stuff. That brings me total joy! How cute is Frosso in our striped pants?

Madeline Swanson wore our shoes to two wedding events — this shoe and this shoe! Her wedding was the chicest I’ve ever seen!

Loved this pretty top on Charlotte Parker. She makes it look totally stunning.

  1. I actually learned some great relationship advice from the absurd reality show I am watching while I needlepoint, Married at First Sight. The root of nearly every argument is one of these: connection, power, or respect. Start to notice what keeps bubbling up. I have and it’s been fascinating and helpful.

  2. Our newest Dina (and Mira) is here and I’m totally obsessed!

  3. This show is dumb, but charming. I love Jake Johnson. I can’t help it, I love a Chicago guy!

  4. I made the Herby Rice and Radish Salad recipe from this cookbook for a potluck recently and it got raves. The key is the lemon zest.

And One Thing I Hate

In the summer especially, certain music makes me carsick. It must be core memories of lurching along nauseous in an unconditioned station wagon in the summers of my youth that does it to me. “Sweet Caroline” makes me wanna barf. Bah! Bah! Bah!

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