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Create truly beautiful moments with Pin Me Up Chicago’s team of over 75 expert hair and makeup artists. For on-location glam and exceptional service, contact our team!

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Our artists.
Your inner beauty. 

Pin Me Up Chicago brings out your best side with on-location hair and makeup in Chicagoland

Pin Me Up Chicago captures the beauty in every moment

Since 2009, Pin Me Up Chicago has built a reputation for simple, on-location hair and makeup that empowers every client to put their best face (and hair!) forward. And with a team of over 75 exceptional beauty artists, if you can envision it, our glam squad can execute it!

From weddings and galas, to photoshoots and media appearances, Pin Me Up Chicago delivers award-winning looks with expectation-exceeding service—in the comfort of your own home, venue, or dressing room.

Dana Fountain and Jessica Sylvester are the visionaries and brand-builders behind Pin Me Up Chicago

Dana, Pin Me Up’s lead hair stylist and owner, and Jessica—her right-hand woman and customer service extraordinaire—have grown this beauty experience from the ground up. Since its inception in 2011, the two have used their sharp attention to detail and a wide network of hair and makeup artists to offer to Pin Me Up’s best-in-Chicago services to over 5,000 brides and event attendees across the area. 


Dana and Jessica’s work has been featured on WGN and NBC, but their greatest accomplishment (to date!) is achieving recognition as The Knot’s Best of Weddings year over year. This prestigious honor is awarded to the top 5% of event vendors across the country each year—and Dana and Jessica strive to keep their streak alive for more years to come.

Dana is a beauty & business queen

I love all things beauty and business. There’s something absolutely magical about helping a bride feel amazing, prepping a client for a big photo shoot, and seeing a show-stopping look come together right before a special event. 


In addition to Pin Me Up Chicago, I own several salons, a south loop wedding and events Venue Row 24, I love to help other beauty professionals network and upskill, I distribute an inclusive haircare line, and travel the country as an industry speaker and consultant. I believe beauty is meant to be shared. And I won’t stop until all of Chicago and beyond is glowing with confidence.

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Jessica is the friendly face behind every email

I believe every wedding and event should be stress-free, memorable, and absolutely beautiful. That’s why I take the time to get to know our clients—and take every opportunity to shatter their expectations. 


Confidence is contagious. And there’s nothing better than that moment when a client feels as amazing as they look! 

“Pin Me Up Chicago did the hair and make-up of myself + bridesmaids + the moms at my December wedding, and they did a wonderful job!” 


“Everyone was so happy with their look - especially as there was such great variety in what people wanted :) The team kept us right on time and was a joy to work with. Would highly recommend PMU Chicago!”

Isabelle F.

Google Reviews

Collaborations + Accolades

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