San Diego Hairstylist & Empowerment Coach


Hi! I'm so glad you're here...

Hairstylist circa. '13
Human circa. '94

My name is Ashley 'Chicago' O'Shaughnessy. Yes, I've seen the MadTv skit & I find it hilarious every time. [if you don't know what I'm talking about search, "my last name + MadTv teacher". You're welcome.  I got the nickname, 'Ashley Chicago', from some of my first paying clients. At that time I had just moved to San Diego from my hometown in Chicago and apparently my accent was THICK. Who knew Chicagoans had an accent anyway? Well, it stuck and here we are! Like most Chicagoans, I have a lot of pride for my city but I have now been San Diego living for over 5 years!! I moved out here at 19 with a soul full of passion, determination and my mind on a mission to prove myself. I started at the top Paul Mitchell salon in the industry and worked for some of the best stylists, educators, and way pavers. I've assisted, taught, made videos, done photoshoots, worked for multiple brands, and taken every opportunity thrown my way. It has shaped me into the creative compassionate I am today.

In February 2019 I took a leap of faith and opened up business for myself making ASHLEY CHICAGO more than just a nickname but a business name and a brand. I am an independent stylist that is based out of Santo Tomas Collective in Old Town San Diego. I not only create looks/hairstyles for my clients but form an empathetic relationship. That in itself has led me to my path as a coach! I have a huge passion for health, low toxicity living, & healing our mind, body, soul through bridging the gap in outer beauty and inner wellness.  Join me as I light the way.


                                  Ashley 'Chicago'


Contact Me

NOTE: I am currently a one man band & I always strive to respond as quickly as possible. Throughout the week, while giving my undivided attention to the clients in my chair, I may be unable to answer your call. For fastest response please email or text me with your full name + how I can best help you and your hair needs! I look forward to meeting you. <3

Santo Tomas Collective
2802 Juan St, Suite 18
San Diego, Ca 92110