Hi Friends! I’m Natalie Mason. I live in Charleston, SC and I am mom to Sterling 12 , Frances Moon 8 and our mini golden doodle Dolly.



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Our Chicago Trip

Oct 1, 2019

Last weekend we took a girl’s trip to Chicago. Every year my mom, sister, sister in law and I take a trip. The boys always do a golf trip yearly so we like to do a girl’s trip. Big props to my Dad for keeping my kids solo all weekend, they had a blast with him. We did NYC last year and chose Chicago for this year (any recs for our next spot, we are already discussing locations for next year? ) I had not been to Chicago since I was 23 for a work trip! It was so fun to explore the city. We didn’t have the best weather but that didn’t stop us from enjoying the city and I loved the cooler temps. I wanted to share the spots we ate at, food is always an important part of my travels and all our meals were excellent. In between eating we walked the city and shopped lots of great shopping!

I had lots of questions about my leopard tote, it is the perfect carry on size and fits so much in it! Also wore my Barefoot Dreams dress for the plane ride- the best travel outfit ever.

Leopard Tote

Our first stop after we landed was lunch at Ralph Lauren Grill.

I loved the vibe in here very classic Ralph Lauren.

Living my best life. Sparking rose and the best food.

Dress | Sneakers

My mom and I split the burger and chopped vegetable salad, so good! Also the fries were insanely good.

Did some shopping after lunch. I treated myself to a Goyard which I will show you guys when it arrives. They had to send it off to have my initials put on it. Also got this super cute dress.

Dress (wearing a small)

Happy Hour Drinks at Hampton Social. The cutest little spot.

Dinner at RPM Kitchen, so many of you guys recommended this spot and it was amazing! It was packed we had reservations and still had to wait 30 minutes to be seated but totally worth the wait. Sadly I didn’t see Bill or Guliana- wish I did!

We shared several dishes | Brussels Sprout Salad, Semi Frito veggies, prosciutto ravioli, squid ink crab pasta and braised short rib pasta. Sorry my photos are not better it was pretty dark inside.

Wearing Ganni Leopard Dress size 36.

The next day we shopped a little in the morning and hit up Little Goat Diner for lunch. I adored this place and wanted to order everything off the menu.

We shared the crudités, Brussels Salad, Chickpea salad, fish tostados and BLT.

Wearing | Blouse | Jeans | Sneakers (15% off) | Glasses

I loved all the architecture.

One of my favorite things we did was the architectural boat tour. It was such a cool way to see the city!

Wearing | Dress | Sneakers (15% off)

After the boat tour we stopped by the Restoration Hardware restaurant. Such a cool setting. I went to the one in NYC too and loved them both.

Sunday morning before our flight we had breakfast at Beatrix. This was another spot that came highly recommended. I loved the atmosphere here.

The yummiest honey cinnamon latte.

Breakfast enchiladas

We truly had the best time in Chicago, what a wonderful city. I can’t wait to go back.

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Leave a Reply

  1. I love Chicago! Being a New Englander I’m biased but maybe your next should be: Newport, RI is fun for wine & mansion tours & Boston is fun for food & historical walking & Portland, ME is a brewery mecca & adorable shops!

  2. Dana says:

    Love your gold ring with the diamonds criss crossing. Where did you get it if you don’t mind me asking?

  3. Mary says:

    Boston! So much to see, do & eat.

  4. Ramona says:

    I concur about Boston. Great city!!!

  5. Lori says:

    Which goyard style/color did you go with? I am thinking that will also be my next big purchase!

  6. Taryn says:

    Hello! What is the leopard blouse your sister is wearing in the last few pictures? Love your blog!

  7. Breda says:

    I am so glad you enjoyed it despite the weather! Chicago is a great town.

  8. Jessica says:

    Where did you guys stay? We are heading there in November and trying to decide which hotel!

  9. Nichole says:

    Random random question…how do you tighten the golden goose sneaker laces?! Without them hanging out so long?! Asking for a friend