![Kelly in the City - A Preppy Chicago Life, Style and Fashion Blog](https://kellyinthecity.s3.amazonaws.com/wp-content/uploads/2022/11/1-2.jpg)
Preppy Travel Bags - Kelly in the City
![Kelly in the City - A Preppy Chicago Life, Style and Fashion Blog](https://kellyinthecity.s3.amazonaws.com/wp-content/uploads/2015/11/Stuart-Weitzman-Navy-Lowland-Boots-40.jpg)
Stuart Weitzman Lowland Boots in Navy
![Kelly in the City - A Preppy Chicago Life, Style and Fashion Blog](https://kellyinthecity.s3.amazonaws.com/wp-content/uploads/2017/06/Tuckernuck-Stripe-Swing-Sweatshirt-200.jpg)
Kelly in the City - A Preppy Chicago Life, Style and Fashion Blog
![Kelly in the City - A Preppy Chicago Life, Style and Fashion Blog](https://kellyinthecity.s3.amazonaws.com/wp-content/uploads/2015/11/Sail-to-Sable-Metallic-Coat-74.jpg)
Kelly in the City - A Preppy Chicago Life, Style and Fashion Blog
![Kelly in the City - A Preppy Chicago Life, Style and Fashion Blog](https://i.pinimg.com/736x/0f/9a/8e/0f9a8e3d6e77000015774918f7cd0bd6.jpg)
Kelly in the City - Page 141 of 217 - A Preppy Chicago Life, Style and Fashion Blog
![Kelly in the City - A Preppy Chicago Life, Style and Fashion Blog](https://kellyinthecity.s3.amazonaws.com/wp-content/uploads/2021/01/IMG_7825.jpg)
Friday - Kelly in the City Life, Style, & Fashion Blog
![Kelly in the City - A Preppy Chicago Life, Style and Fashion Blog](https://kellyinthecity.s3.amazonaws.com/wp-content/uploads/2016/07/Mitch-Larkin-Kelly-in-the-City-200.jpg)
Summer Fashion by Mitch
![Kelly in the City - A Preppy Chicago Life, Style and Fashion Blog](https://i.pinimg.com/736x/92/63/bc/9263bc8dfac2790798f2b50ac23ec3a4.jpg)
How to Tuck in a Sweater - Kelly in the City, Lifestyle Blog in 2023
![Kelly in the City - A Preppy Chicago Life, Style and Fashion Blog](https://i.pinimg.com/736x/f3/b9/40/f3b9401c255d1d061da3c45857827690.jpg)
Kelly in the City - Page 4 of 234 - A Preppy Chicago Life, Style and Fashion Blog
![Kelly in the City - A Preppy Chicago Life, Style and Fashion Blog](https://kellyinthecity.s3.amazonaws.com/wp-content/uploads/2016/01/Preppy-Elephant-Shorts-49.jpg)
2015: The Good, The Bad & What I Learned
![Kelly in the City - A Preppy Chicago Life, Style and Fashion Blog](http://2.bp.blogspot.com/-Ly2qHMw7ygw/VbbqvA7RqiI/AAAAAAAAHh4/sAvd3eIXxxA/s1600/Preppy-Cruiser-Bike-2.jpg)
Little Miss Haute Couture: Interview with Kelly of Kelly in the City