What It’s Like Working with a Personal Stylist
Kelly has been styling photoshoots, apartments, friends, family, and boyfriends-turned-husbands for as long as I’ve known her, but these days she’s doing it with strangers through our new Personal Style Soul Searches, and so the title “Personal Stylist” feels a bit more official now.
This is something people have been asking Kelly to do for a long time, and it makes sense why:
I get to participate because we’ve adapted this new offering from the Soul Search we use with businesses on their brand strategy, and because one of my roles in Kind & Funny as Sidekick / Director of Intelligence is Lead Question Asker thanks to my background as a music journalist.
We started with a few test-case clients to hone our processes, and so far people seem to like it:
“OMG! Absolutely loooooooooooooove this!!!! … SO PUMPED & THANK YOU BOTH FOR YOUR CREATIVITY I’M SO EXCITED TO BE FLOWY, FREE & DRAMATIC ON-STAGE AND IN-LIFE!!!!!!!!!!!”
“YO THIS DOC IS F—ING FIRE. LAYERED CREATIVE - I LOVE IT. I'm so pumped. I feel so seen, empowered, and clear. Well done!!! This is excellent work 👏🔥👏”
I thought I’d share a few things I’ve learned working next to Personal Stylist Kelly on these:
Everyone wants to feel comfortable in their clothes, but everyone has their own idea about what that means
Each person said they want to feel “comfortable,” and then each went on to describe completely different versions of what that feeling means to them.
Comfortable that they will be seen a certain way in certain situations? Comfortable no matter the time constraints in getting ready? Literally physically comfortable? Warm enough because they run cold? Full of confidence in a scary situation? Inspirational to themselves and others? Ready to go from their couch to a Zoom to a networking meeting?
You can start to see how this concept of comfort is expansive and personally unique, which makes figuring out what an individual means when they say “comfortable” one of the most fun parts of my role.
Another most fun part is seeing Kelly translate those feelings into a cohesive personal style and empowering the person with actionable steps to achieve those feelings, which I think is her own particular brand of magic that shows she’s working in her Zone of Genius.
People think there are rules to personal style, but Kelly does not
I think this concept is best represented by the fact that Stacy London and Clinton Kelly from What Not to Wear, a show that taught younger Kelly a lot about fashion back in 2003, are now back in 2025 with a show called Wear Whatever the F You Want.
In our interviews I’ve heard a lot of talk about fashion rules, colors that are supposed to be good or bad for certain skin tones, and thoughts about what people are “supposed” to look like in certain situations (i.e., what not to wear), and it’s cool to see people empowered by the freedom that Kelly invites them to join her in (i.e., wear whatever the F you want).
Instead of rules, Kelly uses the concept of “style pillars” to help guide her decision making when choosing an outfit. For her, she reflects on her pillars of “Cool,” “Comfortable,” & “Creative” when choosing what to wear. Part of our Game Plan is to give each person their own style pillars, essentially flexible guidelines that promote creativity instead of rigid rules that restrict it.
Why are flexible guidelines better than rules when it comes to dressing up? For that I turn to what Rick Rubin writes in the excellent book The Creative Act: A Way of Being:
“Holding every rule as breakable is a healthy way to live as an artist. It loosens constraints that promote a predictable sameness in our working methods … Any rule is worth testing, be it conscious or unconscious. Challenge your assumptions and methods. You might find a better way. And even if it’s not better, you’ll learn from the experience. All of these experiments are like free throws. You have nothing to lose.”
Listening to people is a great way to see them
We ask a lot of questions to learn a lot about people in these Soul Search interviews, and while I think my question-asking game is on an extra-good streak because I just finished the book Supercommunicators, even I can’t take credit for the quality of the conversations we get to have.
People tell us about the times that they felt most like themselves in life, and those are wonderful stories. They tell us about past fashion experiences that hurt, and I can feel the pain. They tell us about their goals for the future, and I can envision those goals being achieved.
We then translate what we hear in these interviews into a Game Plan full of writing and imagery and activities, and the first time we shared one of these documents the person responded, “I feel so seen.”
At first I said to myself, “All I did was listen to what you said and then try and give you what you asked for,” but by the third time I started to realize that listening deeply is my own unique brand of magic that I get to bring to the process, and something that I’d benefit from remembering to do more often.
You can always surprise yourself
While it’s easy to call Kelly a personal stylist, I did not ever think I’d have a claim to the title myself. Most of the fashion sense I currently possess was benevolently forced on me over time by concerned parties, or borrowed from someone who went shopping with me, or given to me as a gift so I’d look better. I would say I improved gradually over time, but didn’t develop a sense of personal style until I bought into Kelly’s ethos that clothes are an avenue for self-expression that can reflect, enhance, and even change the way you feel.
It’s been a long style evolution from when I would judge if my clothes matched by confirming if any sports teams used the colors in a uniform, and if I can do it (with Kelly’s help) then I’m sure you can do it (with Kelly’s help).
I think it’s very cool that she can teach you how to use getting dressed as a way to express how you feel and how you want to feel, and while I still find it slightly unbelievable that I can too, it’s always good to be reminded that anything is possible.
If you feel like the way you dress isn’t matching up with the person you are today or the person you want to be tomorrow, Kelly and I are here to help.
Do you need some help defining your personal style for life, an event, or the next step in your career? Check out our Personal Style Soul Search. Want to talk about something else? jed@kindandfunny.com.