The Wedge
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April 12, 2017

#Originators: Jess Ann Kirby

We want Jess Ann Kirby’s wardrobe. Her minimalist outfits, with casual-cool vibe, are endlessly refreshing. Her website, formerly Prosecco & Plaid, depicts a coastal lifestyle and her love for adventure.

Jess is a former city dweller who left corporate life to return to the coast of Rhode Island. There she pursued her dream of creating a space to house inspiring content and celebrate creativity. And on top of all of that, she’s her own boss. exists to encourage women in all aspects of their lives, and for that alone, we’ve made her an #Originator.

Learn more about Jess in our Q+A below. Featured Style: Jess wears the AMBOY slide in Etiope.


KE: You write that is a 24/7 job, and we believe it. What’s it like to work for yourself and be your own boss?

JAK: A few years ago I honestly never would have thought I’d be my own boss. The only thing I wanted when I graduated from college was a 9-5 and a steady paycheck. But I quickly realized that did not give me fulfillment.

Being your own boss can certainly have it’s challenges but it’s also incredibly rewarding. It’s so cliché, but when you have a job you love it truly never feels like work. Knowing that I am responsible for my own success makes me work that much harder. I can’t imagine now, not having the freedom and independence I get from working for myself.

How were you able to handle the transition from the world of nine-to-five to self-employment? If you could take the plunge again, is there anything you’d do differently?

I am incredibly thankful that I had traditional 9-5 experience. I learned so much from my years in a larger corporate environment. While working in a creative field and being your own boss is quite different from working at a large corporate firm, many of the same basic principles apply. Being professional, courteous, prompt, and giving 150% to everything you do will take you far. If there’s anything I could do over, I would have saved more before taking the leap, building a business from the ground up takes time, and it costs money.


Tell us about your personal aesthetic. Do you have a fashion icon?

Growing up in New England has really informed my sense of style. Living near the beach, growing up playing sports and being outdoors I’ve always gravitated towards un-fussy style combinations. I’ve never been one to spend thousands of dollars on clothing, it’s really important to me that my style is attainable for my readers and followers.

I’ve always been inspired by women like Olivia Palermo and Kate Moss who are the masters of mixing high-low pieces and making it look effortless. I love Iris Apfel because she’s just so cool and dresses to make herself happy, she doesn’t care what anyone else thinks. My personal style is all about being comfortable, chic, confident, affordable and effortless.

Tell us about your shoe closet. As a self-proclaimed tomboy, is comfort a big deal to you?

Comfort is SO important to me. Living in an old New England town by the water, I need shoes I can wear to the beach or downtown to get dinner. With old cobblestone streets that are hundreds of years old, you won’t fine me in stilettos.

I absolutely love KANE and the AMBOY sandals from your spring collection. They’re super cool throw on and go styles that I can wear anywhere the day takes me.

Let’s talk 2017. What’s one goal you plan to achieve this year? And what’s one destination you must visit?

It’s so crazy to say this but our main goal this year was to buy a house and we actually just moved into our first home last weekend. It’s a fixer-upper so we are really excited to get our hands dirty and make it our own (on a budget of course). We have a lot of travel coming up but I’m most excited about my trip to Panama at the end of the month.


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