Should We Ever Stop Playing Dress Up?

[Interview by Maayan Zilberman]

Debra and Maryann share a love of fashion and creativity. Like many of the women I photograph, they feel that style should be fun and not taken too seriously. Each one of them has a unique sense of personal style, but their approach to life and dressing is very similar. Both of these wonderful ladies will have a featured section in my upcoming book . Do you think that we should ever stop playing dress up? Check out Maayan Zilberman’s great interview with the Debra and Maryann below and decide for yourselves.

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We have to get over these outdated assumptions, that women (or men) can only wear certain things.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.

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!

  • A fun and lovely interview of two very lovely ladies.

  • How fun and fantastic. I agree with them. There don't need to be any pre-conceived notions about what's appropriate at whatever age. Fashion should be expressive and your youthful attitude will show whatever your age.

  • How fun and fantastic. I agree with them. There don't need to be any pre-conceived notions about what's appropriate at whatever age. Fashion should be expressive and your youthful attitude will show whatever your age.

  • Love love live thIs!! So inspiring!! What a fantastic attitude and outlook…. It give out courage and insight…


  • Leslie Gelber

    Love it! Off to layer my New York thrift finds right now.

  • omg i love this post i truly do! wow i totally agree that style should be fun and not taken too seriously!

    That is the motto love and live by!

    btw this is my favorite blog!

    happy holidays

  • Debra is just so gorgeous!

  • No – we should never never stop playing dress up!

    The Styleseer

  • sandy

    Just wonderful…remember the 60's song…Express yourself. Well you women are doing it in style…

  • What a great question and great answers. I love the post. For me the answer is never. Playing dress up is just to much fun, :-), Susan Cooper

  • Fantastic interview and I adore these ladies! We should all be so lucky to be around such free spirits!

  • Thank you for such a wonderful post! No, we should never stop playing dress up! 🙂

  • Anonymous

    Not sure what these two are trying to prove – that age and style are not related? They are certainly proving that! Unlike most of your other ladies who are the epitome of elegance, these two just look like late middle age messes instead of young ones! Sorry, they just don't do it for me.

  • Anonymous

    I disagree with anonymous 5:05am December 16,2011. I don't think they look like "messes". I think they look creative and creativity is their style. Everyone has a different opinion about "style"; but to single these two women out and call them "middle age messes" is disrespectful.

    I could see if you said I'm not quite feeling this outfit; but to call them "messes". Please.

    I wouldn't call anyone on this blog or off a "mess"; what they do is none of my business.

    I was raised that if you can't give a compliment or make constructive suggestions, then what you're saying is not at all helpful.

    Maybe I stand to be corrected; but I think Ari's goal is to show that all these women have something to offer. They are expressing themselves. I don't think his goal was to put them on the blog to be ridiculed. Of course there is freedom of speech and you're entitled to your opinion.
    I see some styles in some posts which I don't resonate with; but I just move on, instead of doing "name calling".

  • One should never stop playing dress up! I'll be 57 in a hair over a week, and I haven't started 'dressing my age' nor do I intend to, unless I get a job that demands I do so.

    I think society is far too rigid in what is 'appropriate' for different ages, genders, classes. What does it hurt if someone has pink hair or is wearing a tutu? There is enough harshness in life; one should take joy in the things they can!

  • They got more style in a finger than many others "it-girls-wannabes"
    They are fantastic, i wanna be like them in the future

  • debra rocks color like no other.xx

  • What fun! These women and ADVANCED STYLE are so inspiring. At almost 60, I so appreciate that you are knocking down the old saw that older women must dress to disappear. Thank you, Ari Seth Cohen!

  • What I like best about these two lovely ladies is that it's just so obvious from looking at the pictures that they're friends and they're having fun together. What a blessing at any age!