This week I had the opportunity to meet up with Debra (a fixture on Advanced Style) and MaryAnn, who you all got to see in photos when Ari visited her home to see all the heavenly jewelry she makes. As we ate lunch (at Debra’s favorite of 30+ years, “Spring Street Natural”), the ladies got to compare their views on style, health, and aging gracefully. They even shared some of their stories of dressing up when they were children!

What are some of your earliest memories of expressing personal style?

Debra: I grew up in a very creative and open household, my parents encouraged my sister and I to play dress-up with clothes and to express ourselves. I was always very opinionated about layering. When I was 4 yrs old we moved to Florida, and I had a cotton harlequin jumpsuit that to me said, “THIS is Florida!”… It was my first favorite item; it was freeing and made me feel like I could do no wrong in it. Dressing up was always fun, it was never precious or formal.
MaryAnn: When I was a child, my aunt was a buyer for the upscale department store Gimbels (this building is now the Manhattan Mall in Herald Square!) so I got to browse her closets and have access to all the high fashion items. She would send me boxes and boxes of outfits, and every time they would be more fantastic. I got to learn early how to play with style, and none of it felt precious. Because it was a gift, nothing ever felt off-limits to play with.
Debra: (chimes in after we realize how similar their approach is): If you want an item in your wardrobe, you have to enjoy it…. Don’t be too precious with special items, make them casual- like a diamond brooch on a t shirt, or a tutu as a shawl… its about incongruity!

Do you feel like age should affect how much skin you show?
Debra: I have a great neck and shoulders, thanks to yoga and good genes, so I like to bare them. I’d say that every woman should try things on before purchasing them or leaving the house, because sometimes you think it looks like too much but its gorgeous.
We have to get over these outdated assumptions, that women (or men) can only wear certain things.
MaryAnn: A smart woman knows how to play to her good side, with the operative word being PLAY. Dressing up should be fun; you can’t take it too seriously.

Many women I talk to have a hard time putting together an outfit, or as we might say, “building a look”. How do you get dressed in the morning?
MaryAnn: Dressing up is a creative process that brings me closer to my “Self”. It doesn’t really occur to me that people would have a hard time with this; it’s a natural part of my day. My husband asked me recently “What would you call that look?”, and I answered, “It’s just me!”
Debra: Building an outfit is a morning meditation. It gets me prepared for the day ahead, and is what will determine my mood for the day.

(Last week I asked Debra to take me to Forever 21, a low-priced trendy fashion chain, so I could see how she would build a look with her “Frugality is Fun” mantra in mind. Without a second thought, Debra chose five or six structured dresses or corset-style bodice tops as the base of each look she would create. This would be the answer to all my questions about Debra… I needed to know, as an artist, what would be her “canvas”? She then layered all sorts of blouses, skirts, hats, etc. What you’d never expect, however, is how she treated each item- she’d turn it upside down, inside out, whatever way would work. It’s all about approaching clothes (and life) from a new perspective.)

What would you say to someone worried about age taking a toll on his or her appearance?
Debra: Wrinkles? If you have wrinkles I’d say… So what?! If you eat right, you’ll feel right. You have to keep this consciousness into your 40s, 50’s, 60’s and on…
MaryAnn: In order to keep looking young you have to do youthful things, like dressing with expression. If you feel young mentally, you will look young.
Debra: As you get older you have the confidence to take different style risks, which is inherently youthful.

How do you transition your look into hotter summer months?
MaryAnn: I wear a lot of leather layers all year, but I play with it, less layers and lighter weight. It’s the same aesthetic though. The jewelry I wear changes, I use more seasonal materials, like shells, for summer.

Who are your favorite designers?
MaryAnn: I’m in love with the Rodarte girls. Those sisters are the most creative designers right now; I love their aesthetic and fabric combinations. My dream would be to meet them.
Debra: I love the look of Rick Owens, and Comme des Garcons, but its more for inspiration- once a year I splurge on a designer item, but for the most part I like to work with what I have and just explore different looks.

Do you swear by any beauty regimens? How do you have such amazing skin?
Debra: I really don’t buy products, my main rule is to only use on your skin what you would consider putting in your mouth… so I use a lot of oils like jojoba, olive, etc… I just recently started using Weleda products; they make a lot of creams for babies.

What items do you think every woman should have? And does this change as you get older?
MaryAnn: You always have to have accessories, and lots of jewelry…. And black ribbon. I often have some in my purse if I need to tie something, or I put it in my hair.
Debra: Yes, everyone should have layers of accessories, and recycled items (things you use for more than one purpose)…. I always have velvet ribbon or elastic ribbon around to use as a belt, headpiece, bracelet, or for my hair.

What about someone who’s never tried dressing this way, what if they want to try something new?
MaryAnn: So much of the time people are cemented in their ideas of dressing and don’t want to change their look to be more creative- I used to try giving more friends advice, but its hard as you get older to change these habits!
Debra: To succeed with this I think you need to take it 180 degrees… go to thrift shops so the changes are less of an investment. Spend very little on just a few things so you can play and see what you want to do to express yourself. Go buy some new eye shadow, get a free makeover… anything that feels like PLAY!