Style Advice Q & A

How to Be A Creative Dresser

Creative dressing over 50
Deborah and a friend who enjoys creative dressing.

Dear Deborah, I‘m enjoying your blog. Your advice is wise and practical, yet fun, too!  I’m a 55-year-old empty nester, and a professional freelance writer and artist. For fun, I work part-time as a background extra for feature films.

I’ve always enjoyed clothes and expressing my creativity through what I am wearing, but I’m often confused by the fashion advice in magazines and books supposedly geared to women my age.

One book I picked up discouraged wearing prints of any kind; another touted Pucci prints as the fashion solution to everything. So much of what I read for women my age is so contradictory that I’m confused, and a little depressed. At this age, I’ve got the time to reconnect with my creativity and am always looking for new ways to express it.

My wardrobe is part of my creativity, and I look forward to exploring new ways to look like me. I’d love to learn how to incorporate trends without looking trendy, and how to wear classics without looking same-old, same-old. Please help.

Thanks, Cindy

Sarah Jessica Parker
Sarah Jessica Parker is known for her creative dress!

Dear Cindy,

You’re not alone. Many women over 40 feel a need to express their creative sides, but what defines creative dress?

Creative Dressers Love to Experiment

A creative dresser has fun with clothing. She’s not bogged down by fashion rules. She likes to play with different shapes, styles, and colors and doesn’t take fashion too seriously. She understands the importance of surprise to excite and delight!

Sarah Jessica Parker is a great example of a creative dresser.  She takes her inspiration from everywhere and always wears an unusual mix of things and looks fab. She is confident in her choices and playful in her fashion attitude. Diane Keaton is another.

Diane Keaton
Diane Keaton is famous for her creative style.


Let’s look at some creative dress ideas.

creative dressing Sue Donelly
Image consultant Sue Donnelly is a true creative!

To Be a Creative Dresser: 

1. Wear Unusual Color Combinations

Black+ red can be too boring for a creative dresser. Creative types are more inclined to choose Teal + olive green,  purple + orange, or some other very non-traditional, stand-out color combos.

creatve dressers
Creative dressers take risks and have fun!

2. Experiment with Shapes

Creatives often like to highlight the unusual shapes of their garments and not the body the garments are on. Instead of focusing on dressing for their body types, they wear unusual cuts and styles to express something they are feeling or thinking. Asymmetrical styles, balloon-shaped silhouettes, and high low hemlines are just a few favorites of creative dressers.

3. Don’t Be Afraid to Mix Patterns

Creative dressing = lots of patterns all mixed together. The more, the merrier because it creates interest and excitement.

Get creative dressing ideas
Unusual shapes and fabrics are part of the creative dresser’s wardrobe.

4.  Layer with Abandon

The texture is fascinating to creatives, so one way to do that is layering.  A jacket over a vest, a vest over a shirt, a shirt over a top. Layer away for a funky look.

Get creative dressing ideas
Creative dressers layer their clothes and like unique colors and accessories.

5.  Add Stand-Out Accessories

Creative dressers like to show they are unique and what better way to do that than with some eye-catching accessory that tells a story. That’s why anything vintage from a Victorian pocket watch to a 1930’s paisley skirt is so precious to creatives. These things have character.

6. Try Deconstructed Clothing

Deconstructed Classics which are wardrobe staples reimagined in a way you’ve probably never seen before, let alone even dreamed of and they look very creative.

classic deconstructed tops

If you have a more artistic style personality you will immediately gravitate towards this trend. Choose the right pieces, and deconstructed classics are a fun trend that ups your style cred instantly. Get it wrong, and you run the risk of looking like Edward Scissorhands ran amok in your closet. This simple pieces get it right!


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20 thoughts on “How to Be A Creative Dresser

  1. Thanks for the great tips on dressing “creatively” for older women. All of these tips are workable and fun. In a previous comment, one of your readers asked about vintage clothing. I often shop at thrift shops and vintage clothing stores, but as you suggested, I am careful about how MUCH vintage I wear at the same time.

    For instance, I will wear vintage bangles and bracelets — fun to collect and wear together — with a simple, modern outfit. Or I might wear an interesting jacket from a thrift shop with a new dress or pants. The trick is to combine the vintage items in such a way that they don’t look like a costume — but add to your own unique style.

    My latest find is a tropical print tunic/dress from the 80s — that I wear with leggings, gold sandals, and modern jewelry. It doesn’t look too dated, just slightly Boho and summery.

  2. How can a woman of-a-certain age look sexy and fun without looking like
    a desparate old cougar? I love color,love prints,and I am obsessed with
    anything retro.Can you help me not to look like a crazy person?

    1. Hi Tonja, Of course you can and you sound like you are having fun with your wardrobe. However, trying to wear retro after a certain age can be tricky, so I don’t usually recommend women over 40 and beyond wear it head to toe.

  3. Deborah,
    I love your site and you are helping so many women today! I am 60 years old, 6′ tall and a size 8/10. I now look for tunic length tops just to be long enough for my long torso. I used to buy XL thinking that they would be longer and I just LOOKED FAT. Thanks for helping me see that I needed to buy medium and tunic length to look slim! I have received compliments from people thinking I lost weight and all I did was choose better fitting styles!

  4. Ok so as I check out this site (and I do like the what your trying to do) however your not realistic for 98% of us! For one in case you haven’t heard there is a lot of obese people out here…and it dosen’t take much to be one and wearing a 16-18. NOWHERE do I see anything available like the skinny 20 something models are wearing and am old enough and wise enough even if there was…once you are a size 18 it just goes all wrong! Also we are a casual dress society not a powdered up painted up “glamor” people…how about some good everyday about the town looks..that means practical, usable and fun to wear….carry on

  5. I think your advice is right on. Read your massive mistakes article and am moving away from black as a staple in my wardrobe. I do have to comment though on the age of your models… if 40, 50 and 60 are so fabulous – why are you using models who are clearly only about 25?

    1. HI Geralyn,
      Your complaint about the age of the models is a common one I hear. The only problem is I’m hard pressed to find clothes that you can buy in stores that I think are of good quality and style that don’t use young models!!! I do try to show “real” women once in a while but overall I’m stuck with what the stores have for me to use.
      I hear you loud and clear and wish I could find women models that were more our age!

      1. For creative dressing ideas go to pinterest boards and etsy and places where big, older women post their
        fashion choices.

  6. I’ve been checking out your website and it’s been a real inspiration – tucked myself into a MEDIUM after reading your article on dressing “baggy”….little black number, short, with rousching (?) on both sides – verrrrrrrrry slimming – never would have DARED without reading your tips. THANKS~!

  7. Hi I am going to a dance and the dress I have bought is about 3 inches above my knee. I am 48 and still have shapely slim legs but dont want to appear as mutton dressed as lamb. I was told years ago that if your showing a bit of leg then you shouldn’t be showing cleavage which this dress doesnt. Do you think this length of dress sounds acceptable for my age? yES IT IS


  8. I am loving your blog/web site. Thank you for your guidance. Now that the weather is tuning hot. I would love some casual ideas for staying cool.

    Thank you!

  9. The tie waist pants are a trend. Though I wear them, I tie (without a bow) and slip the tail inside. Thus a t-shirt or other top drops over the waist without the “bump” showing. On rare occasions, I tuck a shirt inside allowing the bow to show.

    1. Hi Celeste
      If you already have this type of pant that is a good idea to tie it the way you suggest. Also, if you are one of those gals with a pear shape body or with a flat tummy you can tuck in your shirt…this style can look adorable.

  10. Great advice here – I just noticed a bunch of tie waist shorts on sale and I’m glad I read your comments first or I might have been tempted to try a pair.

    1. Yes, they look so good on the mannequins but to try to put an outfit together with them is a nightmare, with that big “bump” you are stuck with!
      No wonder they were on sale!

  11. ladies,
    I love your website. I saw this dress this morning and I loved it. I left and went shopping for my 30th class reunion and saw this dress at Steinmart for $39.99. I had a coupon so I spent $35.00. I would have never picked it out but it is so cute and colorful. It is a little low in the back so I put on a shrug. I had already used my fake bake tanning spray this week so I had some color. You should try fake bake airbrush. It gives a very natural look. Thanks for the idea. I look forward to more!

    1. Hi Beth,
      Great to hear it and you will look FAB! Send me your picture and I will put you up on the F40 Facebook page so you can be an inspiration to others!

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