Well Heeled

Blogger goes to town with a finished look

Jacqueline Ward Images

Jessica Fay knows motherhood doesn’t have to mean baggy sweatpants. Instead she promotes bold and bubbly colors, pretty prints and practical heels.

Necessity is the mother of invention, and for Seaside resident Jessica Fay, that adage couldn’t have been more true when she launched Lipstick, Heels & A Baby in late 2012. Initially begun to serve as an online diary that would keep her husband up to date while he was deployed to Afghanistan, the catalogue of daily life at home with a new baby quickly became the creative outlet that she had lost in giving up her job as a hairstylist. 

Fay is, at heart, a fashionista and a girly-girl, a lover of all things pretty and pink. Coupled with her business sense and her understanding of how to appeal to an audience, Lipstick, Heels & A Baby has become a blog that promotes products in a space that creates conversation with the reader. You’re invited in to talk to a girlfriend with great style and a desire to tell you everything about it, from where she got her socks to what she drinks in place of coffee now that she’s pregnant with her third baby. 

Gaining a sense of knowing Fay and what makes her tick only requires a trip around her blog. Her fashion sense is accessible and demonstrates that you really can — and should — make it a priority to feel confident and beautiful even in the midst of a hectic life.

“Style is really defined by personality. It should represent who someone is and what they love, and that’s one thing that’s so great about it. There are no rules to follow, and you can dare to be different,” she explains. “I like to think of myself as happy, bubbly, witty and, unfortunately, slightly spastic, all of which I feel my style showcases perfectly. I translate it into lots of colors and playful pieces. Overall, I want to look polished yet fun!”


Staying polished even in the midst of motherhood doesn’t come without its challenges, as Fay has learned. “You don’t have to sacrifice style when you become a mother, but you do have to keep practicality in mind,” she says. “You’re not going to catch me chasing after two little boys in stilettos! When I’m choosing shoes, I tend to go for thick heels, wedges and flats. I also wear a lot less dresses — again, for the same reason. I don’t want to pull a Marilyn Monroe in the grass of Seaside Square trying to run after the kids!”

Running after kids or running a blog, 30-year-old Fay knows the importance of looking put together. “I’m constantly having to ‘show face.’ Whether I’m doing a drop-off at school, meeting my girlfriends for lunch or going to a PR meeting, I want to always look finished,” she says with a pause and a knowing smile. “Plus, if I’m not presentable, my 4-year-old will ask me why I’m taking him to school in my jammies.” 

Top closet essentials for this fashionista mom? Here are the ones that Fay says should always make the list:‚Äč

  • High quality, classic leather jacket in black or cognac
  • Distressed jeans
  • Neutral cardigan for winter 
  • Fun beach cover-up for summer
  • Neutral heels
  • Cute summer sandals or wedges
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