Date: Jun 23 2025

Filed Under: Fashion, What I'm Wearing

Warning: this is a big post :) There’s just so much to share.

Getting the invitation to join Shopbop to celebrate the opening of their Pop Up Shop in Chicago was a dream trip for me. I think y’all know that it’s my favorite site. I’ve checked their new arrivals by like 10 AM every morning. I am a devotee. And to see it IRL and hang out with the Shopbop team? Dreams.

Wearing:

black mini shirtdress XS, raffia stretch flat sandals, leather tote bag, black beaded bag charm

Let’s start from the beginning. Travel outfit consisted of a cute Staud set that I saw a friend wearing a couple of months ago. It’s the perfect soft and stretchy set that has a nice weight to keep you warm on the plane!

Wearing:

navy top XS, navy pants S, beaded mary jane flats, coral charm necklace, green quilted tote, blue carry on suitcase

Upon landing and checking into the hotel – Hotel Emily – it’s connected to the Shopbop pop up shop, I immediately tried on the pajamas that were waiting for me in my room. I love the oversized flowy style of these and the fabric is the softest and has a nice little stretch to it.

Wearing:

pink stripe pajamas (medium)

That evening we had a little preview of the Shopbop pop up store, followed by a Rag & Bone cocktail party at Bisous, followed by an intimate dinner with the Shopbop team at Maxwell Trading. That meal was absolutely insane.

Wearing:

orange linen top XS, white barrel jeans 25, stone details strappy flats, leather tote

I had an incredible lunch at Alla Vita with some of the other influncers/content creators that Shopbop flew in for the events. Loved getting to meet Jenna, Brittany, and Charli in person! Of course you know Liz.

Shopbop had the cutest Roxanne Assoulin necklaces waiting for us at our seats!

Wearing:

floral fitted dress, stone strappy sandals, leather tote, black bag charm, gold charm necklace, corded initial necklace

After lunch we went to the Shopbop Pop Up for some shopping – I fell in love with this scarf tie top. I also got this black stretchy dress, this black and white fringe dress, and this green stripe tank! All of which will be coming to Harbour Island with me!

Wearing:

scarf tie top 2, Agolde jeans 25, gold charm necklace

We had dinner at Doma with Aligne and Shopbop, and it was one of my favorite events! It was fun to meet so many Chicago creators. And it was fun to see all of the Aligne pieces styled in different ways.

Wearing:

yellow boucle vest top XS, stretchy mid rise jeans 26, gold toe leather flats, leather tote, black bag charm, teak bangle

Very cool to get to sit with Caroline at dinner. I adore her even more now! Do you follow her Caroline’s Closet Shopbop Hearts page on their site? I’m trying to get her and the Shopbop team to come to Charleston for a pop up!! Fingers crossed.

In room try on with Azeeza, how fun is this dress ~

Wearing:

white floral swishy dress S

And I think that’s it, you guys!! When it was time to travel home I wore this comfy and warm outfit. Again, I can’t handle being cold on a plane. And I’m not normally a jeans to fly kind of girl but these are oversized and super comfy!!

Wearing:

blue lace up sweater XS, white barrel jeans 25

Thank you for making it to the bottom of this post :) Happy Monday!!

PS – I have my Shopbop Hearts Page updated HERE!

Chassity

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