Letting Myself Go — and Not Minding a Bit

I’m pretty sure I used to be cool.

I ran with the popular crowd in high school. I played on the tennis team. I read Seventeen magazine. I went to parties. In college I became friends with just about the greatest people you can imagine. We went on crazy road trips. We blew our minimum-wage incomes every Friday at the mall buying clothes to wear for the weekend’s parties or dates. Our hair-stylist roommate ensured we were always well coiffed, well waxed, and made up just right.

And then I became a mom. And, slowly but surely, I’ve let myself go. And you know what? I don’t mind a bit. In fact, I feel great. Wondering how that’s possible? Let me count the ways I’m bringing frumpy back.

1. I rock the mom bob.

For years I wore my hair halfway down my back. Was it a pain to wash and style? Of course. But did it look great? I like to think so. When my son was born, I didn’t even consider lopping off my locks. He could grab my hair by the fistful, but I wouldn’t budge. I wouldn’t be that mom. And then I realized how ridiculous it was to wear my hair in a messy, unwashed ponytail every. single. day. So I chopped it. I’ve never looked back.

mom bob - letting myself go - boston moms blog
One foot of hair — gone.

2. I wear practical shoes.

My shoe collection used to boast more heels than flats. More shoes for dressing up than for working out. More strappy sandals than flip-flops. But I quickly learned that long walks with the stroller weren’t exactly comfortable in cute shoes. And then my own mom, a 60-something hiking nut who shops the REI sales like it’s her job, sent me this hideous pair of Keens. And now? I laugh in the face of the moms who attempt to navigate the playground’s wood chips in their pretty post-work pumps. And that nanny who makes the 20-minute walk to the library in her platform wedges? She can look forward to bunions, poor posture, and bad knees while I’m still living the frumpy-mom, healthy-foot life.

Keen shoes - letting myself go - boston moms blog
Photo (and ugly shoes) courtesy keenfootwear.com

3. I don’t even know what makeup is anymore.

I’ve never felt completely confident with my makeup-application skills, and I’ve definitely never been a fan of the overly made-up look (or foundation lines, or obviously fake lashes, or crazy-dramatic eyeliner). So when I was learning to navigate life with a newborn and a part-time job, makeup was one of the first things to go. Ain’t nobody got time for that. I do put on mascara about once a week — usually in the car, at a stoplight — when I’m feeling the urge to get dolled up.

4. I bought a backpack.

My son is three, and I’ve never owned a diaper bag. When friends were fawning over their Petunia Pickle Bottoms and their $300 Kate Spade baby bags, I was scratching my head wondering why I couldn’t simply use my voluminous purses. And you know what? I’ve had no problem stuffing all the diapers, extra clothes, pacifiers, snacks, toys, and water bottles in. But the thing gets heavy. And after reading about — and feeling — the shoulder and back stress that can come from carrying a giant purse, I broke down and bought a backpack. A backpack that thing that students and hikers use! And I’m not going back.

Herschel Survey Backpack - letting myself go - Boston Moms Blog
It may be a backpack, but it’s kind of cool looking. Right?

5. I wear leggings. A lot.

When I slipped into my first pair of leggings as a pregnant mom-to-be, I swear I heard angels sing. What a gloriously comfortable thing it is to wear pants (yes, I consider them pants) that don’t lead to a muffin top or squished thigh fat. And the versatility! Leggings can go from day to night, from workday to workout. And remember last winter? When life with kids was all about survival and not about looking like a ski bunny? And we all wore our long puffy coats all day every day and our pants didn’t even show? Tell me I wasn’t more comfortable in my thick leggings than the moms in their too-tight designer skinny jeans.

Boston winter leggings - letting myself go
Day or night, at work or working out, leggings for the win!
Ashley is a Virginia native who moved to Boston — sight unseen — for a library science graduate degree she’s never exactly used. Within a year, she met her husband, a nerdy but handsome health economist. They planted roots in Arlington, MA, had three baby boys (2012, 2015, 2021), and entered the world of foster parenting in between. Ashley spends her days picking up Legos, freelance writing and editing, swimming at Walden Pond, and binge eating dark chocolate in the pantry when her kids have their backs turned.


  1. When I was purchasing my Herschel at Urban Outfitters, the sales girl called me a ‘cool mom’. To top the look off, I wear my comfy Birkenstocks as well. Pretty sure all the young kids are eyeing me up wondering how I got so cool.

Comments are closed.