About Us

Writing an “About Us” sometimes feels a little like writing a dating profile...you want to say just enough, not too much, and still convince people to like you. Luckily, at Why Not Boutique, we believe fashion should be fun, approachable, and a little cheeky…so here goes.

I’m Jennifer Dutkowsky, the owner and founder of Why Not Boutique. I’m a Massachusetts transplant who’s called South Tampa home for nearly 20 years. I’ve always loved animals, stripes, red cars, and laughing until my stomach hurts. Back in 2008, I was working in a cubicle job I couldn’t stand when the idea for Why Not was born. With help from Google, supportive parents turned lenders, and a generous community of fellow small business owners, I figured it out one (sometimes panicked) phone call at a time.

We first opened our doors in 2008 in a small South Tampa location. A few years later, Why Not moved into the 100-year-old bungalow we now call home...an iconic space full of charm and character that’s become part of our story. From day one, our promise has been simple: to offer stylish yet functional pieces that make women feel their best without breaking the bank. I’ve always believed that when you feel good, you do good...you smile at strangers, you hold doors open, you spread that little extra bit of joy into the world.

Along the way, we expanded with Why Tots Boutique, a sister shop for children’s clothing and accessories. That little chapter lasted until 2021, when we closed the kids’ store to focus fully on What We Do Best: creating a women’s boutique that feels like home.

In 2020, just one week into a global pandemic, we launched our website. It’s not perfect, it’s not big-box...but it’s ours, and it connects us with amazing women near and far.

At the heart of it all, this boutique is about more than clothes. It’s about the women who walk through our doors (and scroll through our site). It’s about the conversations, the laughter, the friendships, and the confidence boost you get from finding that just-right piece.

So, if we haven’t met yet, I hope we will soon. Stop by the shop, browse online, or just send a quick hello. Around here, customers turn into friends—and friends into family.

xoxo,
Jennifer