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.
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.”
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!
yay, to contribution from an “older” mom (I’m 57). age inclusivity counts as inclusivity too! more please : )
But wait! What SHOULD I wear to my colonoscopy? I actually need this answer fast…. not kidding! Love this interview!
Hi Jill! I love your style.
Thank you TME for featuring readers of different ages! And as a 40 year old in surgical menopause, I look forward to someday reading about layering for hot flashes. 🤣
Did we just become best friends?!? Do you keep you tweezermans in your car because that’s where the light is best?! Also, while my kids are slightly younger, they’re still older kids and i feel like we have identical parenting styles. For example, i am currently aware of how poorly my boys are doing in school, but only because their teachers keep emailing me about it (virtual school blows for teenage boys, FYI). Love this interview and learning about you, Jill! Being a StitchFix stylist sounds super fun! Way more fun than dealing with hot flashes! 😂
From this almost 53 year old: Thank You! I loved everything about this this interview. I would love to see Jill again…
Jill sounds like a keeper. Style plus a sense of humor about the joy and reality of aging. Would love to see more content for those of us in our later 40s and up.
Jill, what a pleasure to read about you! I’m also really intrigued with your Stitch Fix job. It sounds really interesting and cool way to honor the creative outlet of fashion. Helping people and having to get outside of what you would wear yourself.
Love her style! Please feature more moms-of-a-certain age 🙂
Happy to see an “older” mom and would love to see Jill regularly featured!
Darn, I was daydreaming about pitching the middle aged mom edit 😂 Welcome, and thanks for showing style ones in all ages and sizes!
Jill is adorable and we could be friends! HELL YES to the 50-something perspective on the Mom Edit. At 55 – my style isn’t often represented on these pages, we find ourselves with challenges not found on this site. Yet it’s still fun to check in now and again. Also – Living in SE – would love winter wardrobes for our climate – no jackets or cashmere sweaters needed.
You won’t want to LAYER – you’ll want to UNLAYER – LOL 🙂
Woohoo! How to dress for perimenopause symptoms is exactly the style advice this 47 year old needs. Thank you, Jill, and welcome!
Just something comfortable and easy to take on and off. You might be a little woozy afterwards! Also just so you know you will be almost embarrassingly gassy afterwards! But don’t worry so is everyone else! You probably won’t even know which direction the wind is blowing from 😀
More Jill Calo! Love her style.
I loved reading about Jill! She looks super stylish and it’s fun to hear an “older” voice (I’m 49 myself)! Thank you for featuring her!
Oh my gosh—so excited for fashion tips from someone in my age group! 😊 I’m 58 and struggle with what’s age appropriate yet still stylish.
LOVE The Mom Edit. I subscribed after scrolling through the Spanx story featuring the black pants. Lots of inspo there. ❤️
She had me at “my eyebrows are regrowing in my chin”. Love her!!
Wow! How timely! I love reading TME, but I have been thinking for months now (since I actually have time think a little more thanks to the pandemic) how wonderful it would be if TME featured an “older” mom! I was beyond thrilled to see this Q&A with Jill! I am a 58-year-old mom to a just turned 14-year-old boy and am loving every minute of it! Please feature more articles from older moms. We have a lot of wisdom to offer from a different perspective! Love everything about Jill, from her cool older mom vibe to her tell it like it is stories! Keep up the good work!
Thank you for featuring Jill! As a 51 year old mom with three teens I really appreciate her perspective, humor and style. Every time TME reaches out with a reader poll I consistently reply older moms with older kids. I’m glad to have this Q&A but I feel like having a TME team member who fits this category is much needed and overdue.
I want to be friends with Jill! She had me at “open book” and solidified me at “social justice.” I am 52 and hating this peri-menopause BS that we have to deal with. I have two teenagers and definitely love hearing from an “older” mom who still loves fashion, wants to try new trends, and isn’t a size 00 (not that there’s anything wrong with that)! I live outside Boston but am originally from Michigan (I love all the Michigan stuff on TME BTW) and drive through Cleveland when I go back. Jill, don’t be surprised if I show up on your doorstep with a bottle of wine and some postcards we can fill out together to urge voters in GA to reject voter suppression. Thank you for featuring her!
I loved reading about Jill! Thanks for sharing and hope to see you again soon!
This was awesome thank you for featuring a woman in her 50s, for those of us who are in this age bracket it’s refreshing to see ourselves reflected in a fashion blog post. Jill, you rock!
Jill, I love this and think we could be best friends. I’m a Carrie too.
Fabulous and funny interview! I think we all need to know how to dress for medical appointments. My top tip: don’t wear a dress for a mammogram.
I’d like to add my voice to the chorus that says more Jill, more 50+ women. I love TME and have been reading since Ain’t No Mom Jeans days but as someone who is in her 50s, with late teen kids, and a body that isn’t an extra-small or small but a large (size 14) I’d love to see styles that reflect my reality. Thanks so much for introducing us to Jill.
I love this! I would love more voices like Jill’s!
I loved reading about Jill!!!
This. She is a gem.