the cobbler has shoes

lessons from a styling session with Allison Bornstein

Happy Monday! I delayed last week’s letter not just out of self-serving laziness and perfectionism, but also because my atypically location diverse, jam packed weekend dressing for a wine bar, a dive bar, a concert, a friend’s pop-up closet sale, the dog park, a Bed Stuy coffee shop, a birthday dinner at a jazzy club, a club club, plus errands, really put the Allison session lessons to the test. I did wear one of the outfits her and I made together, but actually ended up putting together three new outfits (using some tricky pieces I didn’t even show her) with ease thanks to the revelations had.

two new combinations I put together myself (both in a rush!) after meeting with Allison

Sometimes it’s too beautiful outside to spend all day inside scrolling Pinterest and playing free dress up with TikTok hacks, so today’s letter is dedicated to the magical number of things you can accomplish in just one hour of a paid styling session, and later in the letter, how to pick the right type of styling service for you.

I met Allison Bornstein in late September 2023, one month after moving to New York, at her book tour event at the Theory Meatpacking store. During Q&A, someone in the audience asked about Allison’s ethos around incorporating trends into one’s wardrobe, to which Allison replied that she saw a TikTok with a good answer to that, scanned the audience, pointed to me, and said “Can you share that! What you said in the video…that was so good!” Allison and I had been following each other for a short time, so I wasn’t sure that she would even recognize me, let alone reference my content.

Everyone silently shuffled in their seats to posture themselves towards me. I turned bright red and croaked past some dormant phlegm to quote my own corny metaphor from my TikTok to a room full of people who were not there to see me. Nevertheless, I think this video is the most frequently quoted back to me because it gets at a core pain point at the intersection of the age of information and mass interest in honing personal style.

the beginning of cow coat era. You can still rewatch the videos on my TikTok but God, you had to be there. THE RUSH. Palpable

We are inundated with content and inspiration almost at an even faster pace than microtrends, which begs the question, has this accessibility of information actually made styling any easier for us? Free is great and observing a “relatable” regular person’s style instead of an editorial spread is certainly appealing, but how do we find clarity in this sea of endless inspiration, product recs, hack videos, ootds, hauls, aesthetics, lifestyles, and brands? Enter the original solution: ye old personal stylist.

The last few months, I’ve experienced the client side of a dedicated personal styling session from two of the best: creative director/stylist/Tibi alum Dione Davis and stylist/author Allison Bornstein, and want to share the vastly different things I’ve learned from each of these formats. Of course this letter turned into The Next Great American Novel (at least length wise) when I attempted to cover both sessions in one letter, so Allison today, Dione tomorrow!

My Hour with Allison

Although Allison is far more experienced than I am, I still imagine some people would ask why I would pay someone $300 (I did pay for this btw) to do what I now do for a living. I think generally people (me being people) are not adept at perceiving ourselves, and there’s too much shit out there to process on one’s own. This session corroborated my inkling that I can successfully clock only about 65% of my own bullshit.

For all the benefits of free content, I frequently exit Pinterest or Tiktok feeling inspired, yes, but also like I just increased my to-do list tenfold, whereas leaving these style sessions felt like some of the work just got done. I’m wondering now if this is how people feel when I style them. Asking for help is ok! Getting support feels good! I didn’t realize how seen I would feel having someone else style me for once.

I used my computer to FaceTime her in daylight, and angled my screen towards my open closet so she could see it. If you’re able to do so, this was really helpful during the call as she was able to say “I see a red thing back there, what is that? Can we use that?” which helped to make combos based on things I may own vs. general ideas. Using my computer to call also ensured my phone was available to take photos of outfit combos we made.

When You’re Holding a Hammer, Everything Looks Like a Nail