#377: LoveShackFancy Founder on Selling Dresses Out of Her Trunk, Pushing Past Your Comfort Zone & Turning Her Side Hustle Into a Fashion & Lifestyle Empire

Feb 16, 2026

01:04:40

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In this week’s episode, we’re re-airing one of our top episodes with Rebecca Hessel Cohen, the founder and CEO of LoveShackFancy, a fashion and lifestyle brand know for its unique floral prints and bohemian dresses.

LoveShackFancy was born out of necessity when Rebecca was in search of the perfect bridesmaid dresses and was out of luck. After creating her own designs, she garnered lots of support from family and friends and began selling dresses from the trunk of her car and the rest was history. Born and raised in New York, Rebecca was surrounded by fashion starting at the age of 4 and her story is nothing short of spectacular. Today, LoveShackFancy has gained mass appeal from her vintage-inspired details, flattering silhouettes and playful dresses and ultimately catering to all age groups.

The ultra feminine super-maximalist clothing and lifestyle business now has 17 retail locations in the U.S. and is continuing to expand. What started out as a dress company in 2013 has evolved into an all-encompassing lifestyle brand selling fragrances at Sephora to kid’s clothing and a home collection that is set to launch later this month.

In this week’s episode we chat about her upbringing surrounded by fashion, her early career as a fashion editor and why she felt like it was time to do something different in her life despite her incredible career. We talk about how her interest making a few pieces of clothing turned into a successful side hustle and eventually years later, her full time gig. Rebecca opens up about how many people told her that the feminine prints and vibe would never sell, and that her brand’s name was horrible - and why she didn’t let that stop her. We also chat about the unglamorous days of building the brand, overcoming fears in business, and using social media for success. She stresses setting boundaries, LoveShackFancy's mission, and shares dos and don'ts for running a business for over a decade.

In this episode, we’ll talk to Rebecca about:

* Rebecca's upbringing influenced her early fashion and confidence. [04:03]

* Impact of Rebecca's mom on her upbringing. [06:31]

* Rebecca’s fashion ideation process. [08:32]

* The concept of LoveShackFancy. [10:25]

* Starting LoveShackFancy as a side hustle and career pivot. [13:49]

* Dealing with the fear of change. [21:14]

* Confidence in LoveShackFancy’s vision. [23:36]

* LoveShackFancy’s first store and Rebecca’s key learning. [27:14]

* Juggling high in-store demands and early social media presence. [31:13]

* Balancing business with motherhood. [33:37]

* Launching fragrance and partnering with Sephora. [40:30]