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Join the Pin Me Up Glam Squad!

Ridiculously talented? Love delivering top-notch service? 

Pin Me Up Chicago is always looking for professional, proven freelance makeup artists and hair stylists to help show off Chicago’s good side, one event at a time. 
Ready to be one of them?


Pin Me Up is the premier hair and makeup artist source for weddings, special occasions, and other picture-perfect events. We’ve earned a reputation for offering unparalleled client- and event-focused professional glam services, and fun, fast-paced beauty industry jobs. The demand for top-notch, on-location beauty services in Chicago is growing—and so are we!

We’re currently looking for stylists and artists with any (or all) of the following qualifications (and the portfolios to prove them):

  • Makeup artists skilled in traditional and airbrush applications

  • Eventworthy updos and “down-do's” 

  • Hair and Lash Extensions 


At Pin Me Up, the right chemistry is just as important as your professional skills, certifications, and experience. Our positions are offered to candidates who can easily demonstrate:

  • Proven skill in your chosen craft. This means a deep portfolio of your work as well as the ability to successfully perform a trial as part of your application process.

  • An eye for detail—and an ear for understanding. So much of what we do is rooted in clear interpretation—both of what it looks like, how it ties into the overall event, and why it matters to the client. Our most successful stylists and artists know just how to bring out the best in our clients—starting with asking questions, soliciting feedback, and just plain being friendly.

  • A willingness to learn. Beauty, trends, and styles are always changing—much like the clients we serve. We offer professional development for a reason. We value a craft commitment that starts with creativity and curiosity—and doesn’t stop there.

  • Weekend Availability. As wedding and event specialists, most of our opportunities occur on the weekends (mostly Saturdays). This is the nature (and beauty) of the job. Weekday or Sunday trials are also available—name your preferred dates, and we’ll work with your schedule.

  • Organization and communication skills. Highly skilled stylists and artists have a keen ability to assess and communicate how long things will take, what products they will need, and how to manage stress without making it contagious.

Don’t quite have these skills yet?
Our apprenticeship programs and classes will teach you everything
 you need to know about becoming a confident freelance artist!


Benefits and Compensation

In exchange for your talents and exceptional client care, we offer competitive rates, a fun team environment, and a packed booking schedule that will keep you as busy as you want to be!

Our Hiring Process

Step 1


To be considered as a candidate, please fill out this application to tell us more about yourself, your approach, and why you’d be a great fit for our beauty industry jobs.


Be prepared to share links to your online portfolio and/or high-res pictures!

Step 2


If we’re a great match, we’ll reach out and schedule a virtual interview via Zoom. 


During this interview, we’ll talk about your goals and why you love your job. Then we’ll share a few more details about partnering with Pin Me Up.

Step 3


If selected, we’ll arrange a time to meet in person so you can do a live demonstration of your talents. 


At this time, we’ll not only assess technique, but also your customer care, organization, and overall approach. 

Ready to start something beautiful? 

So are we!

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Explore our (showstopping!) work

Follow us @pinmeupchicago for bridal hair and makeup ideas, effortless event updos, and more. 

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