Meet Jenna (aka "Lunchpails & Lipstick")! - Westport Moms

How old are your kids and how long have you lived in Westport? Hi! We are the Crandall family. I’m married to Dennis (aka “D”) and we have lived in Westport for almost 4 years. We have 3 kids. Davis is 12 (7th grade), Gwen is 9 (4th grade) and Chloe is 8 (2nd grade).
How did you end up where you are now in terms of your job, or whatever passion project it is you might be doing? I started my business 7 years ago when we lived downtown NYC. My mommy website at the time was called “Mommy In Manhattan.” I had three little kids and we bounced around the city creating city guides and fashion ideas for other moms. It was the journey that launched me into my fashion and lifestyle blog, LUNCHPAILS & LIPSTICK.
What is your favorite family activity to do in Westport or the surrounding towns? We love the summer in Westport. We absolutely love spending days and evenings at Compo beach, paddle boarding and of course ice cream at Saugatuck Sweets. We love restaurant hopping and walking Main street. Right now we are obsessed with Ka Wani and Oko for date night. Our family loves Bar Taco and the new Meatball Shop in town.
What’s your favorite app right now- for you- and for your kids? My favorite app is called eero. It helps me monitor xbox, i-pads, phones and the TV’s in our home. I can pause any of these devices at anytime and have the peace of mind that my kids aren’t on devices or sneaking them when they aren’t supposed to be on them. This is definitely not my kids favorite app…lol.
My kids love Wordscapes.
If you could pick one restaurant or store to come to Westport that isn’t here now, what would it be, and why? We need Nordstrom!
What are you most excited about in life right now? Living in a new school district (we just moved to Long Lots) and having a great school year. I’m so excited to get involved and meet new people. My kids are so excited as well.
What is one thing people would be surprised to know about you? I actually can be really shy. Most of the time I force it when I meet new people or take meetings for my job but it’s something I’ve worked on my entire life.
If you weren’t doing what you are today, what do you think your career path might have been? I’d be working for a doctor or running my own Med Spa. I’m an esthetician (15 years!) and still love skincare so much.
If you had 24 hours to do whatever you wanted – what would you do? Go to the spa, lunch with my friends, bike around town and watch a movie with my kids.
What is your most marked characteristic? Sunglasses and hats
What was your most memorable family vacation and why? We took the kids to London and Paris last summer. I still dream about some of the things we were able to experience as a family. Watching my kids get excited about history and other cultures makes me so happy.
What is the best white lie you have told your kids? The ice cream was left out all night. (I have an ice cream addiction) or… Ask your dad; he is so much smarter than me. (when homework at 11pm comes up)
What is your proudest mommy moment? Looking down at my c-section scar and knowing I got my 3 babies here safe and sound. It wasn’t an easy road and I truly think moms are superhero’s.
What do you most value in your friends? Loyalty
What is your greatest regret? Whenever I miss opportunities to put work down and be with my kids. The next day I regret those types of things so much. I’m really working on it. Nobody wants to live with that kind of regret. They are only young once!

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