Friday Flashback! 7 Awesome Moms Rewind to their Favorite “First Day”

In honor of the first (unofficial) week back at school, we asked seven awesome moms to throw back to a memorable “First Day” moment…

The first week back at school is an exciting, often scary, sometimes meltdown-inducing time for our kids. We asked a few awesome women we know, who also happen to be moms and total bosses in their fields, to share a time in their lives when they were on the cusp of a life-slash-career-altering moment, and maybe weren’t sure whether things were going to be okay 🤹‍♀️ 

In their own way, these seven women told us that they felt the most confident and badass in outfits that felt the most like “them.” Which is exactly what we’re all about at Rockets of Awesome! Take it away, ladies… 

Alexa Von Tobel, Founder & Managing Partner of Inspired Capital 

“When I dropped out of business school in 2008 to start LearnVest from a couch, there were a lot of unglamorous moments. On the flipside, one of my favorite special outfits was this red dress I wore on my first magazine cover with Forbes in 2014. (Coincidentally, I was pregnant with my first daughter, Toby, at the time!)” 

JENNY FLEISS, CEO and Co-founder of Jetblack & Co-founder of Rent the Runway

Rent the Runway Founders Jenny Fleiss (right) and Jennifer Hyman

“As two women launching a venture [Rent the Runway] that was being covered by The New York Times Technology editors, we knew that a surefire way to embrace our brand while standing out… was to wear outlandish rented dresses and climb on ladders in our warehouse. This image helped launch our success and is a very fun memory for me and my co-founder [Jennifer Hyman]!”

Marnie B. Nussbaum MD FAAD, Dermatology and Aesthetics

“This was my first day opening my own dermatology practice. I wanted to wear something that would represent my personality, and truly feel like me (I love pink and Chanel). I truly believe [you should] wear what brings you joy and confidence!”

Aliza Licht, Founder & President of Leave Your Mark

“File this under: Trying to look like an executive. I was pitching a new client! This look screams boss, no?” 

Rachel Blumenthal, CEO and Founder of Rockets of Awesome

“I’m in the showroom of my jewelry brand Rachel Leigh – the first business I built – during market week (when we would show the line to buyers). My office was on West 38th Street in the heart of New York’s Garment District. I can’t believe I remember but I’m wearing a Yigal Azrouël dress, and this was definitely my version of a photo shoot back then 🤦‍♀️”

Alex Friedman & Jordana Kier, Founders of LOLA

Alex Friedman
Jordana Kier

Alex: “This is LOLA’s first-ever photo shoot from right when we launched (I’m holding the A from a LOLA balloon set). I remember feeling a little bit of pressure for what to wear, but opted for something that made me feel comfortable, cheery, and like myself.” 

Jordana: “The outfit I wore to LOLA’s first-ever focus group right when we launched. I’m dragging [our] product around in that grocery bag (and now wondering: why did I not bring a tote?).” 

Click here, here and here for more stories of women we think are awesome!