style story: jessica defino

When I joined Substack a little less than a year ago, one of the first people I was starstruck by was

Jessica DeFino

. Her writing and takedown of the beauty industry is so powerful and has clearly made a difference in many of her readers’ lives. I felt like she was doing with the beauty industry and beauty standards what I wanted to do with the fashion industry and the “rules” we’ve been taught to follow when getting dressed (although on a much larger and more impactful platform). When I was conceptualizing this series, she was one of the first people I thought of because I selfishly wanted to know how her ideas on beauty have translated to her wardrobe. You’ll love hearing her take on clothes, and incidentally, not sure how we’ve gone so long without it, but I believe this is the first official mention of “What Not to Wear”, which I know we all have big feelings about. Enjoy!

Q: Introduce yourself, your work, and how you spend your time.

My name is Jessica DeFino and I’m a freelance beauty reporter. I started out as an editor on the Official Kardashian-Jenner Apps in 2015 — I’m sorry! — but being immersed in that world eventually made me question everything I thought I knew and loved about beauty. I pivoted to industry critique after that, and wrote for outlets like the New York Times, New York Magazine, and VICE. Now I have a monthly advice column at the Guardian called Ask Ugly and a weekly beauty newsletter called The Unpublishable (to be renamed soon). I spend a lot of my time thinking, reading, and writing about Beauty, obviously! I spend the rest of it feeding the local ducks and swans, and/or sitting on the beach at the Jersey shore where I live, come sun or snow.

Q: What was your style like when you were a child?

I played dress up everyday. I wore the hell out of that My Size Barbie skirt. As I got a little older, like pre-teen and early teen years, I wanted all my outfits to elicit SHOCK and AWE… bright colors, funky shoes, and lots of strange purses. I used to carry around a huge black patent leather purse that had a working clock on the front of it! I had Parcel boombox purses in every color. 

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)?

One of my earliest fashion memories is getting this grunge-y floral hand-me-down dress from an older girl who lived on my street — this was probably 1996 — and trying to wear it to church one Sunday. My Dad wouldn’t let me wear it and I wouldn’t change, so we both stayed home having a stand-off while my mom took my brothers and sister to church alone. (This is how I remember it, at least.) I guess I learned that clothing is very powerful but also that neither of my Fathers — earthly or heavenly! — approved of my outfits. Later on I learned about “flattering” clothing from What Not To Wear reruns. I got very into 1950s pinup style as a result, since that was the most flattering look for my big chest, wide hips, and relatively small waist. I basically put on a Dita Von Teese costume every day from the ages of 17 to 21. 

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)?

There was the quirky pre-teen “look at me” phase, and then a teenage boho-chic Olsen Twin phase, and then the pinup phase, and then in college I started working at a designer consignment shop so my style was everything and nothing all at once… I’d go from a classic DVF wrap dress and heels one day to ‘80s Versace jeans with a bustier the next to a diaphanous Chloe dress the week after, then resell it all at the store when I got sick of it. So many beautiful clothes, so little personality! (Of course I started a fashion blog at this point.) I got into 1960s-1970s bohemian rock ‘n’ roll aesthetics after I moved to Los Angeles in 2012, and my style has pretty much stayed there since. Flowy dresses, band tees, boots, Birkenstocks, vintage fur coats, leather jackets, suede mini skirts and shorts, feathered blazers, embroidery, big jewelry. One thing that’s remained consistent throughout all these eras: my disdain for basics. I don’t like boring clothes! I can’t bring myself to spend money on something blah!

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 better question: How have they not? I guess I've always dressed for others, but to say something about myself. The things I've wanted to communicate about myself have changed over the years, from I'm not like other girls! to Please, I'm begging you, hit on me and show me I'm loveable or at the very least fuckable! to My body is somewhere under this kaftan and I'm not letting you see it because I want you to understand that I am more than a body, I am a vibrant/multidimensional/dynamic human being!

Q: How have your sense of style and shopping habits shifted along with changes in your body?

I shop online more now that I’m older and wider. I used to love scouring thrift shops and vintage stores for a good deal or a one-of-a-kind piece but now that’s too frustrating. (Nothing fits!) And I’ve added more jewelry to my wardrobe. (Always fits!)

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?

My boobs are my main barrier. They’re pretty big, and I hate wearing a bra, and it seems there are exactly zero clothing designers catering to customers with big, sagging, braless breasts! The flowy boho pieces I love are generally sized and scaled for waifish women, which, like… why? 

Q: Do you have any style icons? Who are they?

Oddly, two Edies: Edie Segwick and Little Edie (Edith Bouvier-Beale of Grey Gardens fame). Both were so singular, so themselves. Also Mama Cass.

Q: How would you define your current relationship to clothes and style?

I’d prefer to be naked but a muumuu will do.

Q: What makes your style authentic to who you are today?

My current style is kind of bohemian and eccentric and all over the place, which feels appropriate because I don't really know who I am most days (beyond a flesh-bound manifestation of love and stardust). I hate when I read an interview and the subject is like, “I’m very confident in who I am” or something. How? How do all these people know who they are? Enough to be CONFIDENT in it?? I have no clue! Maybe someday I’ll figure it out but also I doubt it… The universe is vast and the possibilities are infinite.

Q: Do you wear anything that’s conventionally considered unflattering?

Oh, almost exclusively. (See above philosophy on muumuus.)

Jessica, it’s truly been an honor to have you! I particularly enjoyed the eBay links to some of your earlier fashion staples 😍. P.S. I think eccentric *is* a whole style.

Paid subscribers, read on to hear three of Jessica’s wardrobe recommendations.

Read the previous style stories -Virginia Sole-Smith:

and Virgie Tovar: