My Favorite Recently Outfits

I learned last year Chicago summers are magical for someone like me who’s skin hates the sun and in general gets cranky when the temps are about 80. Grabbing a leather jacket for a dinner al fresco was SUCH a dream last year and made me a chi-summer believer. This means I get to do some transitional dressing which is on full display below. One day we’re in long sleeves and the next day a one-shoulder bodysuit, just to keep us on our toes.

I am always drawn to sweaters and sleeves when shopping and for reason. I get so much more wear out of them than I do anything short or long sleeved! Many of the items I bought last fall for Ireland I am still wearing.

Monday Vibes

The occasion: I had been in a mental funk with work the last few weeks so I decided to start the week off by co-working at the Wing instead of my usual Thursday. I was getting ready that morning and realized something. Wait! I could just wear…. shorts! I’m not in a real office! I can finally wear a blazer and short set that I never understood before! The possibilities are endless!

What I wore: Ulla Johnson sweater, leather shorts, Zara mules (similar)

Burgers and Cocktails

The occasion: I met my friend Kaiti for one of Chicago’s top-rated burgers and a happy hour at Little Victories in Wicker Park. Kaiti is a great friend from college and we had a chance to reconnect when we discovered we both lived in Chicago.

What I wore: Free People one-shoulder bodysuit, Madewell Jeans and these $40 sandals.

Summer Saturday Kick-Off

The occasion: Italian dinner, cocktails at The Hi Lo and my first Mikos Italian ice of the season.

What I wore: An orange dress that is a few years old (apparently I’ve always been attracted to orange?) and I’ve worn here. Alice and Olivia heels, wicker purse I’ve gotten my $30 out of. (You do NOT need another wicker purse, trust me, one will be fine for years to come.)

Dinner and A Comedy Show

The occasion: Dinner at S.K.Y in Pilsen, Ester Povitsky comedy show at Thalia Hall and a drink after at The Green Tap where I pay entirely too much to play the entire Harry Styles album to patrons of a dive bar on a Friday night.

What I wore: This black dress which has become an absolute favorite. I can wear it off the shoulder for one-shoulder to turn up the heat when I want to. I paired it with my Clare V woven bag that I love so much and handmade gold sandals. Similar sandals can be found here and here.

Co-Working at The Wing

The occasion: Thursdays is our company in-office day. Since I’m a completely remote worker, I go into the Wing in Fulton Market. They just recently opened up so there’s not a ton of people utilizing it which means I often have the place to myself. I love Thursdays in general and only having to go “in” once a week makes me really look forward to it.

What I wore: Red wide-leg pants, white v-neck, blazer, Alice and Olivia heels.

The Happiest of Happy Hours

The Occasion: Meeting up with a photography-client-turned-friend! I shot a wedding on New Year’s Eve 2021. Courtney (the bride) and I have been trying to get together ever since. Our schedules finally aligned and we had a chance to have an espresso martini (and fries!) at Trivoli Tavern.

What I wore: My favorite SEA NY dress I got from Lyndon’s last fall, these slouchy booties and my Clare V woven bag.

Chicago Saturday Plans

The Occasion: My friend Melissa ran the Chicago 1/2 marathon and had a PR! I was so excited for her (and extremely nervous!) and we went to brunch to celebrate. She’s got the Chicago Marathon and the Chicago Triathlon so I foresee more celebration brunches in the future!

What I wore: Ulla Johnson sweater, white jeans, Zara mules (similar) and Clare V bag.

A Night in the Theatre District

The Occasion: I saw Moulin Rouge twice while it was here. I would have seen it a third if I had more time and the tickets didn’t continue to rise in price. Absolutely incredible and I think it genuinely got better every time I saw it. Chicago theatre is just truly the best and I’m so happy to have access to it. This was taken to kick off Melissa’s birthday week and just one of the best Chicago evenings.

What I wore: Zimmerman orange dress, Zara mules (similar).