How to Be a Makeup Artist: This Hudson Valley Guru Makes the World a More Beautiful Place
After getting her start in Newburgh, Alexandria Gilleo beautifies an international clientele of brides and celebrities – and still makes time to meditate each morning.
Photo by Kurt Joseph Photography
Not just anyone can be a girl boss. Although the term flies like wildfire across social media, popping up in perfectly posed photos and hashtagged on au courant apparel, the reality is a much harder thing to realize. As a status, it requires long hours, unexpected setbacks, and a willingness to just keep going when it all feels impossible. Being a girl boss isn’t just a one and done thing, after all. It’s a lifestyle that demands a nonstop rise and grind in pursuit of that passion that makes the toil worth it.
Alexandra Gilleo is a girl boss. As a global campaign and celebrity makeup artist based in the Hudson Valley, she spends her days coloring the faces of actors, models, and everyone in between. On any given day, she could be perfecting a bride’s eyeshadow, getting that barely there glow for a makeup campaign set to grace the shelves at Sephora, or working behind the scenes on a JetBlue commercial. Her laundry list of clients is an extensive one — think creative directors, event planners, and magazine editors, to name a few — with no signs of slowing down, and that’s exactly the way she likes it.
So how is it that the big-name artist got her start in the Hudson Valley? The only way to find out is to go back to the beginning.
Alexandria Gilleo and Joe Namath / Photo courtesy of Alexandria Gilleo
Step One: Recognize the spark
A visual person by nature, Gilleo first felt the pull of makeup while watching her mother apply eye shadow and mascara as a girl. In school, she began skipping her early classes to hide out in the bathroom and experiment with makeup. Although she enrolled in community college, she dropped out three days into lessons in order to pursue her artistic vision. Switching gears, she signed up at Capri Cosmetology in Newburgh and never looked back.
Photo by Kurt Joseph Photography
Step Two: Dare to try
At 18 years old, Gilleo took a leap and founded Bridal By Alexandria, her own bridal brand in the Hudson Valley. Through working with mentors in the region, she learned the ins and outs of what it really takes to make it in the industry. She embraced the dirty work, doing everything from cleaning brushes to grabbing coffees, and absorbed all she could about networking and working with a variety of faces.
As one of the youngest makeup artists in the Valley, Gilleo knew she needed to always be a cut above in order to establish herself as the real deal. She made up for her lack of years of experience by booking wedding after wedding — as many as 150 a year — and perfecting her signature “no makeup” look.
“I became really focused on learning how to perfect skin,” she recalls. “That’s when I discovered my niche, [that] I absolutely love skin-focused work. Trends come and go but healthy, beautiful skin is always in.”
Photo by Kurt Joseph Photography
Step Three: Build a foundation
In the beginning, bridal makeup was the main focus for Gilleo. She chose the field not just for the chance to be part of someone’s special day, but for the opportunity it provided her to create covetable results under pressure.
“You have to work on different types of skin, different eye shapes, and sometimes you’re in a small hotel room with old yellow light fixtures bouncing light off the walls that casts shadows and different false undertones,” she says.
Although she loved — and still loves — crafting dreamy looks for brides across the Hudson Valley, she admits there is a stigma in the makeup industry surrounding wedding work, which is often dismissed as lesser or not creditable enough. For Gilleo, however, it remains a way for her to challenge herself and adapt to less than ideal circumstances.
Step Four: Blend that resume
As Gilleo progressed further into the world of Hudson Valley makeup artistry, she also began taking on commercial projects in New York City. Before she knew it, she was crafting Instagram-worthy looks for celebrities and influencers, working her magic on editorial photoshoots, and creating glowing skin for television and ad campaigns.
“Nowadays, you can walk into any Sephora, Kohl’s Macy’s, and Ulta and see giant posters and photos hanging from the walls with my work on it. You can flip open a magazine and see a beauty campaign I did,” she enthuses. “I was even on an airplane recently and watched my work on a JetBlue commercial. It really is a ‘pinch me’ moment every time.”
One particular “pinch me” moment came when she took a shoot job with Mario Dedivanovic, Kim Kardashian’s makeup artist. After the day wrapped, Dedivanovic was so impressed with Gilleo’s talents that he posted it to his social accounts and hired her to assist with one of his master classes.
Yet even as her career skyrocketed, Gilleo had to balance her ever-demanding schedule with one bump in the road after the next. Over the years, she’s faced an endless slew of criticism that her work wasn’t good enough or that she wasn’t established enough to make it in the industry. She’s been told there are too many people in the industry for her to stand out. She’s suffered personal losses of family and friends.
And still she comes out on top.
“I’ve had people tell me I wouldn’t go far because I didn’t have an agent to represent me. I had people tell me that freelancing is too risky and to get a job with security,” she says. “The same people who told me that 10 years are [the ones] calling me asking if I’m hiring.”
This is one of those holy sh*t, pinch me moments... being in @ultabeauty to pick up some goodies for my clients tomorrow and seeing my makeup work plastered up on those walls around the store feels surreal. I don’t think I’ll never not get excited about these moments. . Work posted for @bumbleandbumble AND @lovephilosophy (you can see both) . To get to this point took A LOT of years, a lot of emails, a lot of free work, a lot of assistance, a lot of REJECTION, a lot of lessons, a lot of NOs, a lot of coffee dates, a lot of travel, a lot of early mornings and late nights, you get the point... . Just remember to go at your own pace and that rejection is protection. It takes time to learn your art or trade, to build confidence, build real relationships with colleagues (who I now consider friends), to put your ego in check, to charge appropriately and know your worth- these are the building blocks of your career. . For those who’ve been following me for a while- it took a minute but eventually it led us here!! ... at ulta... still buying beauty blenders 😂🙌🏼💕 . Don’t stop pursuing what you love!!! X Alexandria . . . . . #makeupartist #makeupbyalexandriagilleo #lovephilosophy #bumbleandbumble #ultabeauty #ulta #beauty #promua #nycmakeupartist #production #beautyblogger #cleanbeauty #hair #fashion #entrepreneur #bossbabe #hustle #girlboss
Step Five: Hustle Every Day
Now a leader in the national beauty sphere, Gilleo spends her days at photoshoots, behind the scenes at television networks, and on set at events. Because each day is so unique, she’s adapted to New York City commutes that last two to six hours and flights that take her around the world. In her spare time — when she has it — she churns out articles for the lifestyle blog she’s maintained for the past ten years. More recently, she’s partnered with beauty brands on content creation and even led a master makeup class in Manhattan with Wander Beauty over the summer.
All the while, she continues racking up her client list with names as varied as ABC, ELLE, Etsy, Microsoft, and Morgan Stanley. On the celebrity lineup, she’s worked her magic on faces like Adriana Lima, Barbara Corcoran, and Paul Rudd. And, lest one forget, she still operates the Hudson Valley bridal studio she took a risk on 12 years ago.
Beauty Sleep is my top tip and favorite tactic to good skin, good health, and a balanced life. Getting 7-8 hours a night is a MUST. (Shout out to all my Mom friends who get 2-3 hours of sleep a night, I credit you MAJORLY) . Sleep is one of the most healing things your body does. It even lowers your cortisol levels (stress hormones) which we could all benefit from. . My cheatsheet to good sleep includes: . 😴 no caffeine after 2pm (this includes green tea) . 🌀blue-blocking glasses at least 1 hour before bed (available on my amazon list for $10) . ⚠️turn off all artificial lights at least 1 hour before bed (I don’t have any artificial light besides my salt lamps and living room lamps which I replaced with dim colored bulbs from Home Depot (I don’t want to F with my circadian rhythm) . 🌙Activate “night shift” mode on your screens and devices in the evenings . 💦I spray magnesium on the bottom of my feet at night (also avail on my amazon list) . 😴I sleep in pajamas every night- NOT gym or lounge clothes . ☕️ Ease into sleep with tea. Mint tea is always nearby. It’s so soothing right before bed and is great for digestion . 🌿I diffuse @youngliving lavender in my oil diffuser . 💧I turn on the humidifier . ❄️I keep the temperatures cooler at night somewhere around 67 degrees . ☁️ @sleepandglow PILLOW. This pillow is EXTREMELY comfortable, comes with a 100% tencel pillowcase which helps prevent fine lines, wrinkles, creases, + broken hair, helps with morning puffiness, protects your eyelashes (great for lash extensions), + was developed in collaboration w orthopedists to ensure a correct sleeping condition for your body (everyone would benefit from this) . 📚 I like to read (a real book, not on device) before bed, right now reading Million Dollar Habits . 💫 Bedtime meditation, my favorite is Healing Breathwork meditation by @sahdsimone on the @insighttimer APP, it usually puts me right to sleep . What are your favorite tips for the best sleep routines? I’m obsessed w rituals + want to know! X . . . . . #sleep #wellness #routine #nighttimeroutine #sleepandglow #glow #glowingskin #skincare #makeupartist #beauty #bblogger #nyc #routinesandrituals #beautysleep #silk
Step Six: Take Time for Yourself
With so much on her plate, how does Gilleo find time to, you know, take a breath?
She makes it.
Because her job demands a bulk of her mental energy and waking hours, Gilleo recognizes that carving out an hour or two to unwind isn’t just appreciated; it’s essential. That’s why, even though the bulk of her work is in New York City, she continues to make her home in Fishkill.
“I want to look at the colorful trees in my backyard, I want to hear the birds and the crickets, and I want to attend the small farmers’ markets and eat at the local farms and restaurants,” she says. “Living here allows me to be able to get grounded, quiet, and slow down from the high energy [of] NYC.”
In her rare moments of downtime, she likes nothing better than to take strolls through Rhinebeck, spend nights out in Beacon, or treat herself with a spa day at Mohonk Mountain House. A marked contrast from the big city chaos, the meditative atmosphere of the Hudson Valley acts as a sort of natural remedy to the metropolitan wear and tear.
“I truly believe beauty and wellness are very interconnected,” she says. “The foods you eat, the thoughts you think, your skin routines, the makeup you wear…it’s all a reflection of your unique beauty.”
Wellness is Gilleo’s life, and she practices what she preaches every day. To look and feel her best, she commits to a solid eight hours of sleep and wakes up early to complete a morning routine that includes herbal tea, meditation, and skincare. On the way to work, she listens to podcasts like The School of Greatness or The Highest Self. Whenever she can, she carves in a workout or spends a few minutes posting content on social media.
In other words, she doesn’t stop.
“My job requires a lot of time, travel, organization, and pressure, so I need to make sure I’m always recharged and on point,” she says. To help with this, she even commits to refraining from television during the week and staying away from electronics two hours before bed. Above all, she always washes her face prior to calling it a night. She is a skincare expert, after all.
I believe that Beauty + Wellness are v interconnected. The foods you eat, the thoughts you think, your skin routines, the makeup you wear- it’s all a reflection of your unique beauty . How are the quality of your thoughts today? Let’s shift them into a positive light. Every time you feel yourself about to complain, compare, or judge- let’s stop ourselves right in our tracks. . How does your body feel? Are you fueling yourself with nourishing foods that boost happy endorphins throughout your brain and make your body feel good or are you loading up on junk and feeling bloated? Are you drinking enough water throughout the day? We typically eat 21 meals a week, can you commit to eating healthy for at least 18 of these meals? . How does your skin feel? Dry, oily, balanced? Are you taking a few minutes out to show some self care to yourself by having a mindful skin routine in the morning and night to balance your skin and help you feel confident and beautiful? . Have you meditated? Or practiced some form of gratitude and prayer? Allow yourself 5 minutes to breathe deeply and journal what your grateful for. . This beauty x wellness approach is rooted from making mindful choices about your body and beauty rituals that align with your personal goals and lifestyle. . Don’t feel super obsessive or restricted with your beauty routines or diet but allow yourself to become aware and conscious. Have fun with the art of becoming YOU. . I am offering digital appointments to help you with your skin and makeup routines right from home. If you want the sign up link, let me know. Otherwise, just continue to follow along. I hope to inspire you, so you can feel like your best self! I love you all! X . . . . . . . . . . #wellness #wellnesscoach #yogi #beautycoach #mindfulness #meditation #iamwellandgood #balance #mindbodysoul #spiritjunkie #mindbodygram #green #skincare #holistichealing #crystals #healing #raiseyourvibration #loveandlight #ladyboss #beauty #beautyblogger #wellnessblogger #lifestyleblogger #bewell #holistichealth #organic #health #makeupartist #promua
Step Seven: Let the future inspire you
While Gilleo’s curriculum vitae is more than a little impressive, she knows that it’s just the beginning. Looking ahead, she’s excited to collaborate with brands she loves and forge ahead with Bridal By Alexandria. In 2020, she may even release a podcast as well.
Even with such a bright horizon, Gilleo never loses sight of her journey to get to where she is today. That’s why she’s the first to champion the importance of dedication, hard work, and passion above all.
“Don’t ever listen to people that put you down,” she stresses. “Most importantly, don’t let anyone fool you by telling you that the market is oversaturated. There is more than enough to go around for us all to be successful. Trust yourself, be yourself, and it will all be worth it.”