Create beautiful moments with Pin Me Up Chicago — now also serving Atlanta and New York. With a team of over 150 expert hair and makeup artists, we bring on-location glam and exceptional service straight to you. Contact our team to make your next event unforgettable!
Our artists.
Your inner beauty.
Pin Me Up brings out your best side with on-location hair and makeup in Chicagoland- and now Metro Atlanta, and
New York City!
Pin Me Up 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 150+ exceptional beauty artists and servicing 2 new cities and counting - if you can envision it, our glam squad can execute it!
From weddings and galas to photoshoots and media appearances, Pin Me Up delivers award-winning looks with expectation-exceeding service—in the comfort of your own home, venue, or dressing room.
Dana Fountain, Jessica Sylvester and
Leanne Lebrilla are the visionaries and brand-builders behind Pin Me Up Chicago
As the co-creators of Pin Me Up Chicago, Dana Fountain and Jessica Sylvester have established a premier beauty experience for the city’s most discerning clientele. Dana, the company’s owner and lead hair stylist, and Jessica, her extraordinary customer service director, have cultivated a brand synonymous with quality and care since 2011.
Supporting their leadership, Leanne Lebrilla, Assistant and Senior Brand Manager, plays a pivotal role in both team operations and brand development. She assists Dana in overseeing all Pin Me Up Chicago’s technicians, ensuring smooth communication, scheduling, and coordination, while also managing the company’s digital presence and creative direction. From maintaining the brand’s visual identity to engaging its online community, Leanne ensures that Pin Me Up’s signature style and professionalism shine through every touchpoint.
Leveraging their meticulous attention to detail and an expansive network of skilled artists, they have delivered best-in-Chicago beauty services to more than 8,056 satisfied clients and counting. Their distinguished work has been featured on NBC, FOX, and WGN, as well as in publications such as Beauty Launch Pad and Modern Luxury. Their consistent recognition with The Knot’s Best of Weddings award and 5-star reviews across all platforms underscores their unwavering commitment to excellence.
Dana is a beauty & business queen
Dana loves all things beauty and business. She is a mulit-concept salon owner, author and seasoned bridal hair stylist of over 20 years. Dana takes the most pride in leading her hand picked and trained freelance team, creating salon spaces for beauty professionals to thrive, and educating across the bridal and beauty spaces on the power of collaboration.
Pin Me Up is backed by a large, diverse, and incredibly talented team—over 150 niche focus artists and counting that can meet any call and bring every client’s vision to life. Dana’s mission is to meet and honor every client’s unique vision of beauty, perfectly pairing each individual with artists who can expertly bring that vision to life for their special day. Dana’s approach centers on renewing confidence and ensuring that everyone leaves feeling authentically beautiful, maintaining a welcoming and judgment-free environment where natural beauty is highlighted and self-expression is celebrated.
Jessica is the friendly face behind every email
Jessica believes every wedding should be stress-free, memorable, and absolutely beautiful. She is the friendly face behind every email, taking the time to get to know each client and exceed their expectations.
Her warm and personalized communication style ensures every client feels heard, valued, and understood throughout the planning process.
Leanne is the brand’s voice, vision, and sparkle
Leanne Lebrilla is the Virtual Assistant and Senior Brand Manager at Pin Me Up Chicago, where she brings both structure and creativity to the team. She manages the coordination and communication of all Pin Me Up hair and makeup technicians, ensuring every artist is supported and every event runs seamlessly.
Beyond operations, Leanne is the creative force behind the brand’s online presence — shaping campaigns, curating content, and keeping the Pin Me Up voice bold, beautiful, and authentically Chicago.
“Pin Me Up Chicago was the absolute best to work with on my wedding day! Nicole did hair and Lily did makeup for myself and four family members, and it was such a treat to spend the morning with them. They helped me make a few adjustments from my initial trial hair and makeup and had me feeling like a million bucks! I'd highly recommend booking with PMU.”
- Cassie L.
Bride/Client
Collaborations + Accolades
