Meet Team SG: Caroline Reilly
lover of menswear and Maine
Caroline Reilly

By Caroline Reilly | Last Updated: Jul 7 2021

Caroline Reilly

Get to know Team SG better with a few fun facts. Want Caroline Reilly (or Kelci, Gabi, Taylor, and Allie!) to shop for you? Learn more here.

25 things to know about men’s personal stylist Caroline Reilly:

1. I have a law degree from Boston College Law School.

Boston College library

2. I have an Italian Greyhound named Rocko.

3. I’m passionate about reproductive rights and justice.

In law school, I worked at the ACLU.

4. My celebrity crush is Peter O’Toole.

Peter O'Toole
via GQ

5. My favorite thing to splurge on is lingerie.

Which means, if you’re looking for romantic present ideas for your significant other, I’ve got recs!

Negative Underwear set
Negative Underwear Non-Wire 2.0 bra, $60

Try La Perla, Cuccia, Simone Perele, The Great Eros, Fleur Du Mal, and Negative Underwear.

6. I have a health condition called endometriosis, and I’m passionate about raising awareness for better care. You can read my take on SG about how to be a good partner to someone with endo right here on SG.

7. As a journalist, one of my favorite things to do is interview costume designers about the menswear looks they create.

I’ve interviewed the costume designers for Succession, The Young Pope, Curb Your Enthusiasm, The Irishman, and The Nanny.

8. My favorite place in the world is coastal Maine.

My family has vacationed on the coast of southern Maine for as long as I can remember, mostly in the York Harbor and Ogunquit areas.

Something about the sea air, the slower pace, and the beautiful landscapes just makes me feel so at home.

More recently, though, my endometriosis specialist is located just outside of Portland and finding him has been a game changer for my quality of life, so it now holds an even more special place in my heart. 

9. I’m the descendant of a tailor who made suits for FDR.

FDR in a suit

10. My first job in journalism was in college at Frontline, the PBS documentary series.

I started out working in audience development and social media. Between internships and summer jobs, I was there for about two years.

By the time I left I was just starting to get into writing pieces for the website, but then it was off to law school!

11. In college I also worked in a fancy suiting store in Boston, which is where I learned how to fit a suit.

12. Speaking of, my favorite party trick is that I can guess any man’s jacket size just by looking at him.

13. My favorite meal is a tie between homemade chicken parm and broccoli rabe with pasta.

And yes, I am Italian. In case you weren’t sure.

14. My favorite writer is Tennessee Williams, and my favorite book is his play The Rose Tattoo.

It’s steamy and gritty and really beautiful.

15. My ideal Saturday? Sleeping in.

Brooklinen bedding
bedding: Brooklinen

That includes getting out of bed no earlier than noon, a late breakfast, a trip to the city to shop, and then home for a nice big home cooked meal.

16. My most sentimental purchase is my Rolex Datejust that I bought after one of my endometriosis surgeries.

I saved up for it for a year and wear it every single day with pride.

17. My go-to perfume is Chanel N° 22. I’ve been wearing it since high school.

During my freshman and sophomore years, I went to school in Boston and I’d go browse around after classes.

One day, I went into Chanel and got a ton of samples of this line of fragrances they have that you can only buy in the store or through Chanel exclusively. I instantly fell in love with 22.

It’s like a slightly more powder-y version of the iconic No. 5 and lasts forever. Literally, sometimes I will shower at night and still smell it the next day.

18. My grandmother, the “Caroline” in Caroline Reilly, was a menswear lover as well. She would keep a box of ties to give away as gifts.

19. I recently interviewed Donald Sutherland about his personal style.

Donald f*cking Sutherland! What an icon.

20. My academic writing on abortion access has earned national recognition and my health journalism on endometriosis recently won a digital reporting award.

21. I’ve never gotten a manicure. I’m a DIY gal when it comes to nails.

Not bad, right?

When it comes to nail polish I like to splurge. I wear almost exclusively Chanel (I know, I know). Their La Base makes a perfect gift as it can be worn under other colors or on its own.

22. My favorite shows are The Sopranos, Boardwalk Empire, Succession, Bordertown, and The Bridge.

23. I much prefer cold weather to hot.

To be honest I get seasonal affect disorder in the dead of summer sometimes.

24. I used to be seriously into ballet, and I took it three to four nights a week.

We’re talking, hours-long practice. So much so that I never had to play sports in school, I always just filled the requirement with dance.

25. I think the hottest thing a man can wear is a crisp white pair of cotton boxer shorts.

ENTIREWORLD Type B Version 2 Slim-Fit Organic Cotton-Jersey Boxer Shorts
Entireworld boxer shorts, $20

Meet more members of Team SG!

Get to know Kelci, Gabi, Taylor, and Allie

clothes hanger

Ready to upgrade your wardrobe? Head to our service page to see how SG can help.