On Farrah: Pink Fur Coat: That Laneway Store | Floral Dress: Ted Baker | Socks: Target | Shoes: Sam Edelman
Red Dress: Parker | Red Coat: J. Crew | Purse: Chloe
Crop Top T-Shirt: Alice + Olivia (similar) | White Skirt: Club Monaco (similar) Socks: Target | Shoes: Sam Edelman (similar)
On London: Pink Fur Coat: That Laneway Store | Outfit: Janie and Jack, 12 Oaks | Shoes & Unicorn: Egg by Susan Lazar
On Gisele: Dress: Janie and Jack, 12 Oaks | Shoes & Unicorn: Egg by Susan Lazar
On Nick: Shirt:  Rodd & Gunn | On Leonardo: Outfit: Janie and Jack, 12 Oaks

Photography: Native Among You | The Fort Co. 

I am sharing some of my favorite looks from our weekend getaway to the Windy City last week where the weather was perfect for cozy sweaters, silk scarves and the chic socks with glitzy heels trend- clearly my latest fashion obsession!

Oh Chitown, where do I begin? It is magical; a place with a midwest attitude and big city vibes. We go to Chicago so often that I have stayed at almost every hotel in the city, but my favorite by far is Waldorf Astoria Chicago. The staff is wonderful, kind and exceptionally accommodating; it truly feels like a home away from home. Not only is the hotel super glam but the rooms are gorgeous and there is beautiful Carrara Marble everywhere you turn. It is the most posh hotel in the heart of the Gold Coast and the location is just steps away from everywhere you want to be.

We stayed on the property all weekend long– except for the short walks to the quaint shops and luxury boutiques on Oak and Rush– and enjoyed all of the amenities and the incredible dining options the Waldorf has to offer. We went down to the Petit Margeaux cafe in the lobby for brunch daily. The menu is short and sweet but nothing short of amazing. The prime rib sandwich was Nick’s fave. I personally couldn’t stop raving about how the espresso beans were perfectly roasted and the French macarons were the ideal mix of soft and chewy and a little bite of heaven in your mouth. For dinner, we dined at the delicious Margeaux Brasserie which is French cuisine at its finest. The salad nicoise is the best I’ve ever had and the menu is the most delightful twist of textures, temperatures and flavors to satisfy even the most sophisticated of palates. The gym is huge and has everything you could possibly need to sweat it out and get some adrenaline pumping.

Whether you are visiting the Windy City for a romantic weekend getaway or looking for a family-friendly vacation, the Waldorf Astoria just gets it. From the ambience to the service to the food and drinks, the Waldorf delivers above and beyond and we can’t wait to go back!

What are some of your favorites in the Windy City? I can’t wait to hear about what you love to do and see; drop us a line in the comments below!

This post brought to you by the Waldorf Astoria Chicago.


  1. These pictures are ABSOLUTELY stunning! Looks like you had a wonderful time! So proud of you!!

  2. AMAZING! Love all of these pictures, such a beautiful family!

  3. Your family is beautiful. Looks like you really had a great time in Chicago. The Waldorf Astoria looks amazing. You and your” mini me” (London) area absolutely stunning in your matching outfits. Gisele and Leonardo are as cute as ever. I wish you and your beautiful family all the happiness in the world. So proud to Call you my friend. I’m proud of all your accomplishments from bring a wonderful wife, mother, friend and mentor. I love you. 😊💜💙

  4. You look so beautiful! Love the outfits on everyone! London, Gisele are absolutely adorable and I totally want that fur!and of course Leo is a stud and will soon be breaking hearts ♥️

  5. Looks like you all had a wonderful time in Chicago. Will definitely have to take our girls to the Waldorf Astoria!

  6. Those are some great photos! What a lovely property — the perfect place to host your gorgeous family! I think I know where we will be staying next time we visit Chicago!

    PS I am in love with that Ted Baker dress! ❤️❤️

  7. Absolutely amazing!!! What a beautiful family and looks like an amazing time in the city. You are such an inspiration to all those stylish mommies out there!! Love it all.

  8. Such amazing and beautiful photos!!! Looks like you and the family had a blast Chicago!! Great photos at the Waldorf Astoria!! Keep up the amazing work!! 😊

  9. First of all, thanks for sharing this! You look amazing !! And I can’t handle your sweet sweet babies 💗💙 I, too, love Chicago! I will have to stay at the Waldorf now when I go!

  10. Everything is stunning! Sounds like a dream. Can’t wait to stay there 🙂

  11. Obsessed!! Such a perfect family😻😻😻❤️❤️😘

  12. I’ve been to Chicago so many times but this post has given me so many wonderful new things to try! The Waldorf looks so beautiful and I know it will be where I stay next time I visit the Windy City! Thank you for sharing all your suggestions and glam. Reading your blog posts make so many of my fashion and getaway decisions so much easier to make. Can’t wait for the next adventure! Xx

  13. Can anyone say, tres chic! Where in the 🌎 did you & London find those fabulous minks? They are absolutely gorgeous! Such a beautiful & classy family. Mommy and daughters are looking head-to-toe glam, while Leo & Nick are turning heads! How was the Waldorf? I have heard nothing short of amazing & I plan to visit there now especially after these amazing pictures! I say, let’s meet in Chicago!!

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