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How Alyssa Whitfield of Dress For Success Works To Help Women Feel Their Best

Words by Marléna Ahearn
Photos by Julia Merrell

Dressed in a Panache-bag-sale-find blazer and layered strings of pearls, Alyssa Whitfield sits back in the boutique-y Dress For Success, eyes tearing up as she recalls some of the recent career wins of her clients. She’s seen people through their lowest lows and helped them dress confidently and professionally for the job or promotion they’re after.

“We provide women in the community with the attire, the resources, and support to go out and not only get a job, but to be a star at work and move into careers,” says Alyssa. “Most of the people we see have been going from job, to job, to job and none of it is really sustaining their families.”

The storefront of Dress For Success is a clean and tidy boutique where clients can come in and feel cared for. No matter their background, Alyssa strives for a very dignified, inspiring setting where people can figure out how to look “the part” and leave confident and prepared for an interview. Each person gets a curated capsule of clothes to try based on their personal style and the job they are after. Alyssa’s one big rule is that everyone has to come out of the dressing room and look at themselves in a large floor mirror—there are no mirrors in the dressing rooms—to encourage clients to get second opinions. Almost everyone leaves with a new bra too, thanks to Vanity Fair.

In the self-described “second act” of her Rochester story, she reflects on her journey, wishing someone had told her as a young adult that there were more jobs in fashion than just designing and retail. But perhaps, without her experiences in both corporate and non-profit areas, she wouldn’t have found her calling in Dress For Success. Cradling a University of Alabama mug (her daughter is a freshman) she launches into a story about how she came to run Dress for Success Rochester.

Back when the Style Network was still on air, there was a show called How Do I Look. One day, Dress For Success was on and talking about how to help people in your community by giving to Dress for Success.

“I looked it up and thought: this is what I should be doing. I looked to see if there was one in Rochester. There wasn’t. But it was always in the back of my mind,” says Alyssa. She started doing volunteer work at Working Wardrobe at the YWCA but craved more. “I never knew where my suits were going or what happened to the person after. I always had in the back of my mind that there should be more. By the time I figured out this is what I should be doing I happened to go back and type in Dress for Success—they were looking for somebody to bring it to Rochester.”

Her role at Dress for Success is not only her calling, but her motivation. Daily she has a moment where she gets to see her work positively impact someone’s life.

“Everyday I get to see someone walk out of here more confident than when they came in. There isn’t a day that I don’t have a client who says ‘I feel ready.’”

On her personal style, Alyssa says she thoughtfully and purposefully buys all of her clothes—and encourages others to do the same. She doesn’t have a lot of clothes, just enough pieces she loves. One of her favorite style tips is to follow the three P’s for dressing with purpose.

“It works for everyone because it’s not about me telling them what to wear, but about their own thinking,” says Alyssa.

The first ‘P’ is to find a Personality Piece, something that you just absolutely love. Alyssa loves her cheetah and leopard print, evidenced by her glasses and boutique. Your personality piece is how people will remember you. The second ‘P’ is your Power Piece. Whether it’s a great suit or a handbag, find something that makes you feel like you won’t go unnoticed. The final ‘P’ is your Purpose Piece. Which is basically your unique style piece. If you love dresses, a dress is your purpose piece. The key is to find staples and basics that serve you and your purpose and then amping it up with the personality and power pieces.

Join Alyssa on February 6th for "Style Yourself Successful" to learn more about style and dressing your best.