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Life and Work with Ashley ‘Chicago’ O’Shaughnessy

Today we’d like to introduce you to Ashley ‘Chicago’ O’Shaughnessy.

Thanks for sharing your story with us Ashley ‘Chicago’. So, let’s start at the beginning and we can move on from there.
A little over 6 years ago, I followed my once upon a time hobby- turned passion. I went to cosmetology school at Paul Mitchell the School in Chicago where I fell in love with the craft of hair/makeup and decided to pursue it in a state I’d never been. I moved out to San Diego 4.5years ago solo where I immediately began working under the wing of many mentors at a world reknown Paul Mitchell focus salon (A Robert Cromeans Salon). After immersing myself in as much education as I could get my hands on, I developed a clientele, knowledge, and experience. I branched out in February 2018 to a salon called, Style Lounge, that I am so proud to call my current salon home! I work with an AMAZING talented team where I am a blonde specialized colorist & haircutting specialists/educator. I love creating multi-dimensional looks – even better if it’s a textured Lob!

A twist to my story is that I actually also do a lot of bridal hair as well! (It was my first love in the hair world!) I love traveling to locations and getting to create beautiful braided, boho looks on brides to really be the icing on the cake of their special day!

Has it been a smooth road?
The hairdresser’s journey is H-A-R-D! It is a career that takes time, patience, and a lot of hard work… but the pay off is so worth it. I get to surround myself with creative, strong, silly men and women in my craft and be a part of something so much more than just hair for the people in my chair. I create a safe space for my clients to unwind, relax, trust, while also feeling beautiful – truly inside and out.

My advice for beauty lovers and future cosmo professionals is to get your hands in as much hair and makeup as you can so that way you can see what part of this industry truly sparks your passion! BUT also learning when to pause and give back to yourself. Filling up your cup in an industry where most of what you do is give, is vital to a long, passionate, successful career. Also, something I felt early on for a portion of my career was pressure & comparison. If I could give my past self any advice it would be to RELEASE the pressure to compare and remember that this is your story: don’t compare your chapter 1 to someone else’s epilogue.

So, as you know, we’re impressed with Ashley Chicago – tell our readers more, for example, what you’re most proud of as a company and what sets you apart from others.
I hold a few different hats! In the salon, I am a colorist, stylist, and hair cutter. I specifically focus on blonding in terms of hair color. I am extremely focused on detailed techniques that mimic a natural look & do blonding/balayage the majority of my work day! I have a deep love for technical cutting and currently am obsessed with shoulder length and above textured looks. I cut short hair using scissors exclusively (no clippers needed here) & love educating my clients on how to style their new look every step of the way. That being said, my first love in the industry was… styling! Updos, twists, braids, you name it. I love on-location work because I get to meet so many different people and usually means me getting to create a look for someone’s wedding day that they’ll never forget. So magical! I would say, I’m best known for my thorough consultations and communication all throughout the hair process.

There’s a wealth of academic research that suggests that lack of mentors and networking opportunities for women has materially affected the number of women in leadership roles. Smart organizations and industry leaders are working to change this, but in the meantime, do you have any advice for finding a mentor and building a network?
Having a mentor is so helpful throughout this career! I believe in having more than one mentor and having them change as you change throughout your career too! All of my mentors over the past few years have ranged from world-renowned hairdressers I’ve seen on stage/assisted to those I’ve met at events, to those I’ve never met but communicate within social media! I highly recommend finding events or meetups that resonate with you and your brand. Getting out of your comfort zone is great but also being true to who you are and what you stand for will only help you find more mentors along the way!

Contact Info:

  • Address: StyleLounge Salon
    540 6th Ave
    San Diego, CA 92101
  • Website: Under construction- stay tuned!!
  • Phone: (619)-501-6821
  • Email: ashleychicago25@gmail.com
  • Instagram: Instagram.com/ashleychicago


Image Credit:

Bronwyn Huddleson Photography

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