style story: jess kirby
what happens when you stop dressing for an audience
I used to follow
years and years ago. She was fashion blogger #goals. Beautiful girl, perfectly photographed trendy outfits, big brand partnerships, lots of followers. The kind of successful influencer who, if I’m being perfectly honest, made me feel like I wasn’t quite doing enough. I lost track of her for a while, but earlier this year, I came across her here on Substack. To my surprise, instead of a highly produced newsletter, Jess was chronicling her journey of extricating herself from the influencer world. I was intrigued - this was interesting. Whether she’s writing about how it’s easier to get dressed when you don’t have to wear different outfits every day for content, admitting that she built a facade online about her early motherhood experience, or hearing what it’s like to go from big brand partnerships to earning $5 at a time for Substack subscribers, Jess is continually impressing me with her transparency and honesty. This post is photo heavy so if you’re reading this in your email, make sure to click through so you don’t miss any of it!
Q: Introduce yourself, your work, and how you spend your time.
A: I’m
, a writer, marketing professional, and travel blogger. I started out in HR consulting after college, then started a blog in 2013 and became a full time fashion/beauty/lifestyle influencer, which I did for the last 10 years. I eventually left influencing because I became so disillusioned with hyper-consumerism, social media, and the fashion and beauty industry. I am also a mother to a 4 year old daughter. I spend my time writing my newsletter A Common Thread, creating content for my blog JessAnnKirby.com (soon to be The New England Guide), trying to survive being a parent in current times, and enjoying where I live, the great state of Vermont.Q: What was your style like when you were a child?
A: It was a bit all over the place, but I also went to Catholic school from 6th grade through high school, so I wore a uniform, and when I wasn’t wearing that I was playing sports, which didn’t give me a whole lot of time to focus on my style. I do remember feeling like “free dress” days were incredibly important and significant.
Q: Growing up, what messages were you given about what you should or shouldn’t wear (and from whom or where do you think those messages came)?
A: At Catholic school, there were a lot of messages around shame, modesty and guilt. There was a strict uniform and not a lot of room for any expression of individuality. It was important to be “good” and fit in. And that stuck with me for a very long time.
Q: How has your style evolved since you were younger and what phases have you gone through with your style (i.e. high school grunge phase, early working days business casual phase, etc)?
A: My personal style has been ALL over the place. Maybe some of that is my reaction to not having a ton of freedom to express myself or individuality as a kid. In college I leaned into “academic” or “professional” dressing. One of my professors would always comment on how it was nice that I got dressed up for class (and reinforced my desire to be the “good girl”). When I got my first corporate job after college I worked at a consulting firm and the dress code was fairly conservative. I rebelled a bit by wearing bright colors, mix match suits, some pretty funky stuff (for that environment anyway). I actually got called into HR about something I wore one day that was deemed “inappropriate.” I was absolutely furious and made a big stink about it. At the time I lived in Brooklyn and leaned into the hipster look and shopped second-hand almost exclusively. When I got into influencing is when I started to gravitate towards trends and whatever was deemed “of the moment” on social media.
Q: How have external pressures to conform to the ideal standard of beauty and the thought of how others view you affected your style?
A: Where do I even begin? Catholic school, being the eldest daughter, doing some modeling as a teen, I very much always wanted to be “good” and “pretty.” I am turning 40 at the end of this year and I finally feel like I am really coming into my own in terms of my personal style and resisting the pressure to conform to certain standards of beauty.
I also now live in a place (Vermont) where conforming to ideal standards of beauty and otherwise just doesn’t feel as prevalent. And that has given me a sense of freedom to exist without certain pressures I have felt living in other places up to now.
Q: How have your sense of style and shopping habits shifted along with changes in your body?
A: Becoming a mother was the single most transformative thing in terms of my physical, mental and emotional being. I wouldn’t say it totally changed my perspective or values, but it gave me a sense of urgency to live more in alignment with those values. From a body changing perspective, after having a child, wearing anything too tight or restrictive literally made me want to scream.
Once I had my daughter it also changed how I felt about being an online person and I became fiercely protective of her privacy. That played a big role in me walking away from influencing. And once I was more on the outside looking in, I became incredibly turned off by the amount of consumerism and waste created by the fashion industry, and didn’t like my role in it as an influencer. Naturally, that changed how I shopped and thought about clothes. It has been a very freeing, liberating and also challenging experience.
Q: What barriers do you encounter in trying to express your style? Are there any situations or spaces you feel your style prohibits you from accessing or gives you better access to?
A: Honestly, I realize (thanks in part to so many other great writers including Dacy and
), because of my size as a thin person, I do not experience many barriers when it comes to expressing my style. I can shop anywhere without worrying about if they’ll have my size. I can wear pretty much whatever, and know I will be perceived a certain way because I am thin. But also, as a woman existing in the world, I still find myself thinking about what I wear and if it will draw unwanted attention/harassment. I was literally whistled at/catcalled on the street recently riding my bike to the farmer’s market. Ugh.Q: Do you have any style icons? Who are they?
A: I’ve been so disconnected from social media/traditional media lately that I’ve been in a bit of a style bubble. It has been fun though, to find inspiration from other people in everyday life. We travel a lot, especially around New England, and it’s cool to see what people are wearing. There’s a real practicality here in Vermont around what people wear. I love seeing how people dress and express themselves while also needing to wear things that are functional/practical. It’s very much a waste less, mend what’s broken, share what you no longer need, type of environment, and it has really impacted how I care for/appreciate and view what I have in my wardrobe.
Q: How would you define your current relationship to clothes and style?
A: I think I’ve come to a place of comfort, acceptance and balance. I want to wear what is comfortable. I accept that I don’t need to buy new clothes for every season or chase every trend (I am currently in a year of “buy nothing new”). I am leaning into enjoying what I have. I feel fine repeating outfits and wearing the same thing again and again. I’ve really been interrogating my urge to buy things and noticing how much my anxiety and need for control drive my consumer behavior. Accepting that there is much around me I can’t control has helped me find balance in how I approach that.
Q: What makes your style authentic to who you are today?
A: My style is comfortable and relaxed, which I think is a reflection of me being comfortable with who I am and where I am in my life right now.
Q: Do you wear anything that’s conventionally considered unflattering?
A: I really don’t like wearing tight clothes. I want oversized and comfy. I basically went on a tear and got rid of every high heel in my closet. If it’s not comfortable I am not wearing it.
Thank you so much, Jess! It’s fascinating to hear about what happens when you go from dressing for an audience to dressing for yourself. Make sure to subscribe to Jess’ newsletter A Common Thread and like or restack this post! ❤️ Paid subscribers, read on for Jess’ wardrobe recommendations.
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