25 Things You Don’t Know About Me: Ashley Grillo

25 Things You Don’t Know About Me: Ashley Grillo

Introducing Style Girlfriend's stylist-at-large
ashley grillo

By Megan Collins | Last Updated: Jun 26 2022 | 4 min read

If you’re texting with Style Girlfriend, there’s a good chance you’ve chatted with Ashley, our new stylist-at-large.

Ash and I met over a year ago – one of those fortuitous, There’s my friend! moments – where, within five minutes, you know this is a person that’s going to stick around your life awhile. And luckily for me, I run a company where I get to hire my friends when they do stuff that’s useful (see: Taylor, Jen) meaning I’m double-dipping in the friend and menswear pro bowl. So! Get to know her, why don’t you?

Below, 25 things you don’t know about Ashley:

1. I grew up in a small town in Connecticut called Griswold (NO relation to Clark Griswold…wish I had a dollar every time someone asked that).


2. We’re talking: a very, very small town. My grandfather raised cows, horses, chickens, pigs and ostriches. Why ostriches, you ask? Pure pleasure (and their eggs hatch just like chickens)!

3. I won the Connecticut State History Fair with a submission about the Tobacco Industry. I was in elementary school, and I still consider it one of my greatest accomplishments. #nerdalert

4. Oh, and I was the first-ever (female and overall) class president at  St. Mary’s Middle School, beating out two classmates to claim the role! Boom. #imwithher

5. I had to wear a school uniform up until I went off to college. Hence, my appreciation for clothes today.



6. I was so chubby as a little girl my dad told my mom I should go to a doctor because he was afraid I would get picked on by my classmates. It was baby fat. I grew out of it.

7. My senior year high school superlatives? Biggest Appetite and Best Dressed.

8. I’ve never met a condiment I didn’t LOVE. Top honors go to tahini, with ketchup coming in a close second.

9. At Thanksgiving, you can have the turkey; I’ll take the sides.

10. The dimple on my right cheek is actually from a car accident in which I completely totaled the car…oops. My grandmother tells me I was touched by an angel (sigh).


11. I’d be very happy to communicate exclusively in emojis or Giphy, especially at work.

12. When I first moved to New York, I didn’t have a job lined up, but I’d saved enough money to live on for a month and found work in two weeks.

13. At my second job, my boss made my intern write all my Christmas cards to my clients because my handwriting is so bad.

14. Growing up, I played soccer, basketball, and softball, and took gymnastics and dance. Not to brag, but I was awesome at all of them.

15. As an adult, I went snowboarding and snapped my wrist while doing a really awesome trick…kidding, I was practicing on a bunny hill and went down – hard. Don’t ever ask me to snowboard.

16. Before heading to the hospital, I stopped in the lodge for a glass of wine. The best decision I made all day.

17. I can justify anything….

18. Really, I’m more of beach girl. I’ll tube and jet ski until the sun goes down.

19. Just like Megan, I was a tomboy with a bowl cut and a Starter jacket repping the Chicago Bulls. Michael Jordan forever.

20. What I love about helping guys improve their style is seeing the way it makes them feel. Some people think clothes aren’t important, but ultimately, the first thing you notice about someone (and what they notice about you) is appearance. That’s true whether you’re meeting a Bumble date for the first time, interviewing someone for a new role at your company, or meeting your gf’s family for the first time. Within those first few seconds, (whether you admit or not) we’re all making first impressions, and all we have to go on at that point is how a person looks.

My goal is to give guys that extra pep in their step to go ask that girl out or a boost of confidence when speaking to their boss about a promotion. Help them stand a little taller, speak a little louder, feel more “in their skin.” That’s all very rewarding to me.

Shopping and putting an outfit together can be intimidating; I’m there to take that pressure off and to give guys more confidence when they step out their door, so they can focus that energy on more important things, work, family, fantasy team…whatever.



21. Music moves me, literally. If I’m ever late, it’s usually because I was busy dancing to something on Spotify while getting ready. Double it if it’s Beyoncé on rotation.

22. Sometimes I cry when I watch The Voice or when my dad puts ESPN’s 30 for 30 on Thanksgiving. Those human interest profiles just pull on my heartstrings. If you can’t relate, I swear you’re not human.

23. I studied abroad in Florence and have been back to Italy almost a dozen times since then. Mostly for work, but I still manage to fall more in love every time.


{Ciao, dove è lo shopping?}

24. Still can’t speak the language fluently, though.

25. The last book I bought was Aziz Ansari’s Modern Romance, while stuck at the airport. I swear I laughed out loud the whole flight back; I’m sure my seatmate loved it.



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I started Style Girlfriend to help guys look, feel, and act their best.