Today we’d like to introduce you to Jessica Taylor.
Jessica, please share your story with us. How did you get to where you are today?
My entrance into the fashion world started at a young age.
My Grandmother Eva from Montreal always inspired me with her interesting fashion sense. She never wore or owned a pair of pants a day in her life, and at 98 – she still wears a dress or a skirt every day! I spent summers visiting Montreal and buying my school clothes in unique department stores and boutiques.
The fashion had more of a European feel. I always wanted to be the trendsetter in school and help friends with their style and makeup routines. A typical get together would involve makeovers, fashion advice and talking about our latest crushes.
Fast forward to my college years where I studied Graphic Design and minored in Communications and Psychology. During that time I began working for MAC Cosmetics where I learned many new makeup techniques. The reason I love being a makeup artist and fashion influencer is because nothing is more rewarding than to make someone feel confident.
After finishing a makeup job, I see my clients leave with a newfound confidence. They walk out of my chair with their head up and shoulders back. I have built long relationships with my clients, some lasting over 15 years. After years at MAC working in management and freelancing, I decided to go out on my own and I created Make Up By Jessica Sara Taylor. I have worked on photo shoots, fashion shows, movies, commercials, weddings and teaching makeup applications.
As much as makeup is a big part of my life, fashion has always been a creative outlet for me. While living in Florida I worked for a start up company that had a shopping app with social media influencers. I decided I wanted to be THAT influencer. In 2017, I moved back to Boston and launched @Jessinthatdress on Instagram. I wanted to stay true to my roots and focus on dresses, find new designers, and bring my followers unique pieces.
They say you never feel like you are working if you love what you do, and I truly love what I am doing. I adore my Instagram friends, working with new companies, and exploring different locations within the New England area. Boston is an exciting place to be and I’m glad to call it home. @Jessinthatdress is a newer adventure and I am so excited to see where it takes me!
We’re always bombarded by how great it is to pursue your passion, etc – but we’ve spoken with enough people to know that it’s not always easy. Overall, would you say things have been easy for you?
It has not always been a smooth road. I have learned many lessons along the way. Not being paid for makeup jobs that I have done and not receiving photos of my work is always disappointing.
Luckily, it only happened early in my career. I think with any job there is adversity that you have to overcome and learn from. I wouldn’t change anything.
So let’s switch gears a bit and go into the Jessinthatdress story. Tell us more about the business.
I am known for being a trendsetter, makeup artist, and a creative businesswoman. I built my clientele by word of mouth and referrals in the makeup industry.
I am most proud of the wonderful friendships I have made along the way and life-long clients. My fashion focus is on dresses. I specialize in having eclectic taste, and you never know what will be posted next. I also like to make my readers aware of the ingredients they use in their cosmetic products and share my favorite organic, non-toxic skin care brands.
What sets me apart from other influencers and as a makeup artist is that I deliver exactly what my clients want. I am approachable. On @Jessinthatdress I always respond and interact with all of my followers.
I think it is very important to get to know my audience. I try to bring different looks to my Instagram, I don’t buy what is trending. I buy and share what I like. I know that is what makes me stand out.
How do you, personally, define success? What’s your criteria, the markers you’re looking out for, etc?
I think success is when you are truly happy with what you are doing, and having close friendships and family. I also think I have reached success when I know I am inspiring others around me. The reason I am so happy doing makeup is the feeling I get watching someone leave when I have completed their makeup. I see a different person, shoulders back, chin up, a glow to their face… a smile from ear to ear. That is what success feels like.
When I post on @Jessinthatdress, I love when a follower reaches out for information about the look or lets me know they went out and purchased my outfit. It is great to be able to share my creativity and style in an unlimited way. I am always looking for the next amazing company to collaborate with. I find the opportunity is what excites me the most.
Contact Info:
- Email: Jessinthatdress@gmail.com
- Instagram: https://www.instagram.com/jessinthatdress/
- Facebook: https://www.facebook.com/jessinthatdress/

Image Credit:
@jaycoyphoto, @sarah.a.coon, @samantha5mith, @gabbybaglieri
Getting in touch: BostonVoyager is built on recommendations from the community; it’s how we uncover hidden gems, so if you know someone who deserves recognition please let us know here.

Suzanne
September 19, 2018 at 11:56 am
Jessica you look gorgeous !