Wine Women & Shoes Fashion Show Feature: Diana Simaan Kessler

Diana Simaan FashionApril 12, 2014 marks the 4th Annual Wine Women & Shoes Orlando. Every year, a committee of volunteers committed to fighting hunger and giving back to Central Florida come together to make every year better than the last. This year will be no exception!  Something we are extremely excited for this year is the fashion show. Joining us this year is Diana Simaan Kessler, who will be premiering her new collection!

In February of last year, Diana launched her line at the New York Fashion Week, and we are both honored and excited she will be debuting her newest collection at this year’s Wine Women & Shoes Orlando!  Learn more about Diana, her inspirations, and what she loves about the Central Florida scene in the interview below:

Have you always known you would be a designer?

Yes.  My mother used to take me with her to London Fashion week when I was a child.  I first expressed my love for fashion at the age of 2 when I hopped up on the runway at a major show during fashion week in London.

What or who inspired the way you design?

I find inspiration in many things, it depends on what I am working on.  Art, travel, architecture, nature to name a few.  The way I design is unique because I use the same philosophy I used when I was an interior designer.  Beauty is important, yet function and quality is also a must.

What is your favorite kind of piece to make?

My faves are dresses and jumpsuits.  All of my collections have at least one jumpsuit in them.  They are so much fun to wear!  I also enjoy designing custom wedding dresses.  It is an honor to work with a bride on one of the most important dresses of her life.

What is your favorite thing to wear?

I started designing because I found it difficult to find clothing that stood out and was comfortable.  So it’s only natural that my favorite pieces to wear are my favorite pieces to make, dresses and jumpsuits.

What do you love most about Central Florida fashion?

The boldness of color.

How did you get involved with Second Harvest/Wine Women & Shoes?

Several years back, my friend Erin Laser asked me if I would be interested in donating a Diana Simaan Inc item to the WWS Key to the Closet benefitting Second Harvest Food Bank.  She introduced me to the chair of WWS Diane Heiken who I have become friends with now.  Giving back to my community has always been important to me and plays a big part of the core philosophy of my business.  It’s wonderful to be involved with such a fabulous group of Central Florida women all wanting to make a difference and have some fun with fashion.  We should all should pay it forward in any way we can.

Why did you choose to participate in the fashion show?

Orlando is my home and my last collection launch was in New York.  I made a commitment to myself that my next launch would be in my hometown and tied to a local cause that benefitted many lives in our community in a meaningful way.  When Diane Heiken contacted me about the opportunity to participate in the WWS Fashion Show, I knew immediately it was meant to be and said let’s make it happen.

What will people love about your pieces?

The timeless style with a sense of edge.  The attention to detail, quality, fabrics, colors and the comfort. 

Thank you Diana for taking the time to let us learn more about your passion for what you do, and your commitment to being a Hunger Hero!

It’s not too late to grab your tickets to this wonderful event. Head over to and remember that WWS is even better with your sole sisters! So make sure to share with friends. 100% of your ticket price will go to fighting hunger in Central Florida. See you there!


Melissa Kear
Online Marketing Coordinator

P.S. Check out some of Diana’s great designers over at

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