Long time listener, first time caller, Jill, hit us with a Power Move of an introduction email: If we were ever looking, she said, for someone who could write about “how to layer for hot flashes” or “what to wear to your colonoscopy” we should let her know.

Power. Move.

For now we’re doing a little “getting to know you post,” but I am making a note about looking hot with hot flashes.

Stitch Fix Stylist Jill Calo On Parenting & Being Inspired

Jill is a momma of six grown kids who also has a penchant for style, fashion and maybe just a little too much love for shopping (what a big mood). I could blab all day about her, but it is soooo much better if she just tells you about herself! Let’s get into it.

Blazer (similar) | Smiley Tee | Pants | Doc Martens

1. Describe yourself in one sentence.

“Can it be a run-on sentence? I am an open book with a very small filter. If by some small miracle, what I am thinking hasn’t come out of my mouth it is written all over my face. My SATC character quiz always says I’m a Miranda, and I’m like, what? I’m definitely a Carrie. My daughter told me once (insert her eye-roll here) ‘Mom, EVERYONE thinks they are a Carrie, YOU are a Miranda with a hint of Charlotte’s anxiety.’ I may or may not have cried when she said that.”

2. Can you give our readers a little rundown on what you do?

“In real life, I am an admissions director at an all-girls independent school in a suburb of Cleveland. I also have a side hustle as a Stitch Fix stylist. In my next life, I’m coming back as a weather forecaster. You can be wrong every day and nobody ever holds you accountable.”

3. Describe your personal style in three words. Who are your style icons?

“Black, black, black. I love everything about Diane Keaton, she is definitely my #1. I also love the lagenlook of the Olsen twins and love Mindy Kaling’s dresses, but am usually not brave enough to wear that much color, and if I do, I usually throw something black on top.”

4. What are the 4 most-worn pieces in your closet?

This Banana Republic Sweater Jogger Set: true to size

This J.Crew Relaxed Cashmere Turtleneck: size up for a slouchier fit

This JJill Ponte Blazer: size down even in petite

These Pilcro Relaxed Jeans: size down

Jean Jacket | Dress (Similar) | Sneakers

5. What’s your go-to outfit? How has your style changed since becoming a mother? (If at all)

“My go-to look for work is usually a black dress, or a colorful dress with a black sweater, cardigan or blazer over top. I like to add color with tights and because I work in a school and wear a mask all day, everyday cute colorful ones are a must. I switch between several pairs of Doc Martens or some kind of clunkier loafer; I love booties! On the weekend, I live in sweater joggers and a matching hoodie, or a pair of jeans, and, you guessed it, a black top. I became a mom almost 28 years ago, so my style has changed a lot! I am more willing to try new trends now and just feel generally more comfortable being my authentic self.”

6. Top three beauty products. Go…

“This one is hard because I don’t use a ton. I can’t live without my bareMinerals Barepro Glow Bronzer, my Benefit Gimme Brow– I think my eyebrows are regrowing on my chin — thanks menopause — and my Great Length hair extensions. They just added new colors that are helping me blend my grey; I stopped dying about a year ago. Oh, wait! I guess my Tweezerman’s would have to go on that list too! (That’s the upside of wearing a mask every day!)”

7. What are the cutest possible shoes you grab when you know you’ll be walking around all day?

“Definitely my Thursday Knockout booties, Doc Martens or my P448 high tops.”

8. What is your favorite place to shop online? What about your favorite place to shop locally?

“I like to support smaller local businesses, but the pandemic has made that hard because I try not to go out unless I am picking up something essential. Most of my packages these days come from Anthropologie, Nordstrom or Garnet Hill, and I have a lot of jewelry from Catbird, a woman-owned business in Brooklyn. In Cleveland, I could not live without Evie Lou for amazing comfortable and stylish clothes, and Lingg Gallery for gifts, plus the occasional splurge for me. Or more than occasional if you asked my husband. I also couldn’t live, literally, without these gorgeous face masks from my friend Leah’s Etsy shop. Local and a Black-owned business!”

Button Down (similar) | Jeans (similar) | Birkenstocks

9. Your side hustle is working as a Stitch Fix stylist. What’s that like? What’s your favorite part?

“I love getting to know people through their style and helping them out of a style rut. As you build up repeat clients, it is fun to develop relationships with people you’ve never met! They share new jobs, pregnancies and other life milestones. I also love choosing items that are a little outside of their comfort zone to mix it up a bit.”

10. Where do you draw inspiration from when styling outfits?

“It can be hard when people don’t have specific requests or haven’t left a lot of feedback on items they’ve loved or hated. I look through their previous Fixes, brands they’ve kept, looks they pin on Pinterest, and on their Fix Inspiration Boards, or their style shuffle. I try to take what I like and hate out of the equation, but sometimes that’s the hardest part! You have to be able to suspend the ‘I would never wear that’.”

11. What 4 pieces are you coveting right now?

Nadaam Heart Cashmere Jogger Set | Pilcro The Slim Boyfriend Jean | Catbird Peaceful Girl With Fist Charm | Farm Rio Aurelie Maxi

13. How do you stay anchored to your passion?

“I am most passionate about Social Justice and Equity and Inclusion. Before my current position, I worked for the Anti-Defamation League for 10 years, and I look at all of life through that lens. It’s honestly not hard, but sometimes it’s exhausting, if that makes sense, feeling like the weight of the world is on your shoulders. It is so important to me, that I don’t feel like I have to work at it.”

12. You have six grown kids! What advice would you give to other moms?

“Aw jeez, I am not sure I’m even qualified to answer this. My kids range in age from 20-28. I gave birth to four of them (which I never let them forget) and have two bonus kids from my second marriage. I would say, let them make mistakes and don’t try to fix everything for them. My kids are amazing and resilient! There is definitely a happy medium between a helicopter parent and what I am. I didn’t micromanage their lives…made them all get jobs in high school and college to pay for things that they wanted that weren’t necessities. I probably could have paid more attention to their grades, but I am sure they are happy I didn’t. The upside of my style of parenting is that they have turned into adults that can manage on their own, the downside is I’ve made myself dispensable 🙂 Oh, and it’s OK if your house is a mess and your five-year-old needs to remind you that they have a dentist appointment.”

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If you want to work with Jill on Stitch Fix you can request her in your notes when scheduling your Fix! We will be looking to feature more readers, influencers, and problem solvers, so keep an eye out on the Facebook Insiders’ Group and the Newsletter for updates.

Thank you, Jill, for doing this style interview with us!

xoxo,

Team TME