Leaping into Feminine Fashion with a Rebellious Spirit

Audrey Collage 2

Lessons of Feminine Fashion from Truman Capote

Did you ever read the book Breakfast at Tiffany’s? Maybe you saw the movie? They were two very different presentations of the world Truman Capote created, but they both had a very feminine rebel at their core in the form of Holly Golightly.

As I work through this month of pushing my fashion boundaries toward a more April in Paris-inspired feminine style, I’ve been thinking a lot about Holly Golightly and the actress who played her in the movie, Audrey Hepburn.

Granted, neither Holly Golightly nor Audrey Hepburn were French. The story itself is based in New York. But both women were icons of fashion’s femininity and they were women who pushed boundaries and challenged expectations. They blazed their own trails, for better or for worse. This speaks to me as I challenge my own notions about what it means to dress feminine, to be feminine, over 40.

Rebelling Against Myself

If I am to embrace their spirits, I have to be willing to be a little rebellious. In this case, I’m rebelling against my own expectations and perceptions.

For most of my life, I have equated feminine styles with itchy lace, cold zippers up the back, and pastels so light that my presence fades into the clouds. In other words, my perception of dressing feminine meant being uncomfortable and invisible at the same time. I totally forgot about those women, like Holly and Audrey, who stood out due in part because of their femininity.

As a result of my perceptions, my go-to colors, patterns, and fabrics have long been more masculine in character. They make me feel stronger, taken more seriously. I perceive these masculine styles as keeping me from being seen as “cute,” a four-letter word most petite women have heard their whole lives and hate. (Just ask Laura, a petite fashion blogger at Collecting Labels.)

So, these masculine colors and styles became my safe place and it’s hard to let go of that. Even in my first post of this series exploring feminine styles, I chose a top that was inspired by men in the French Navy and a pair of boyfriend jeans. To rebel against that, I had to embrace my inner Holly Golightly. I had to go against the grain and try feminine colors, patterns, and fabrics.

My first leap into this more feminine space was with the Fab Collab I did with Jodie of Jodie’s Touch of Style blog. We wrote personal stories about pearls and how they relate to four decades of women, from forty-plus to fifty-plus, sixty-plus, and on to seventy-plus. In writing my part of the collaboration, I had a revelation when I looked at the photo of my mother from when she was 16, clad from neck to knee in lace. My first thought was, “Boy, does that look itchy.”


Truth is, she looks beautiful. But, yes, I have a thing about lace and itchiness. More on that in a post to come.


This revelation, though, made me take stock of my notions about femininity. It forced me to face my addiction to black, tweed, and brogues. I had to ask myself what was so wrong with color and lace. And really, I had to ask myself what was so wrong with wanting to look like a woman.

Even with a desire to change, I had no idea where to start. My notions of femininity were so skewed that when I looked at things online, I became overwhelmed. So, I did what any good writer worth her salt would do — I consulted the experts.

When in doubt, bring in the experts

Elizabeth Podlesnik is a personal stylist at Nordstrom in downtown Seattle. I mentioned her last week when describing her rule of “The Third Piece.” When I met with her, I went in with an open mind, but since my mission was to find feminine styles, I was slightly terrified I might come out looking like somebody’s fairy godmother.

This was silly, of course. Prior to our meeting, Elizabeth emailed me with several questions about what I hoped to achieve and what my current style was like. When I arrived for my appointment, she had a dressing room waiting for me. It was filled with subtly feminine pieces that — gasp — I immediately fell in love with.

She picked out the outfit I’m wearing in these photos, though I added the shoes. Without expert attention from Elizabeth I might never have tried these baby blue ankle pants by NYDJ or paired it with that linen top by Eileen Fisher. I definitely would never have picked that blue floral(!) scarf! Look at me! I’m feminine! And, if you don’t mind my saying so, this outfit is so chic!



One of the things that struck me as I worked with Elizabeth was how simple elegant dressing can be. I’m so used to adding something — a vest here or a jacket there, a big chunky necklace or long scarf, etc.

The outfit Elizabeth created takes a page right out of Audrey Hepburn’s style book with a basic top, some close-cut ankle pants, and a pair of statement shoes. It has that exact sophisticated ease I’m looking for when I think about feminine fashion that embodies the April in Paris theme. Based on the photo comparison below, I could even remove the scarf and still come away looking polished.

Audrey Collage 1

Let’s talk about shoes

The real gauge of how far I’ve come with this little experiment is to check out my shoes. Besides lace, flats are another one of those things I’ve avoided my entire adult life. They have never seemed comfortable to me and I don’t need anything to make me appear smaller than I already am. But these flats from Cole Haan are pointy and ever so leg-lengthening. I will admit they are not the most comfortable shoes I own. I will never walk the dog in these, for example. The chic-factor, though, makes me want to protect them from the perils encountered when walking the dog. I want to save them for times when I’m out to dinner or lunch and for sit-down brunches or concerts. In other words, the positives outweigh the negatives and I fear I must admit yet again how wrong I was.


The Verdict

Looking at this outfit, I see classic femininity. There’s nothing frilly about it, but it is definitely feminine and it pushes me out of my original comfort zone. Even so, I am completely comfortable. I actually feel pretty great wearing this.


Next week I’ve got a special guest joining me. I’ll be chatting with Jacynth from The-Bias-Cut.com about her mission to help women over 40 go against the grain and embrace their signature style. I hope you’ll subscribe to the blog or follow me on Facebook, Twitter, or Instagram so as not to miss a thing!

Shop This Look:

NYDJ ankle pants | Eileen Fisher linen top | Floral blue scarf | Cole Haan red flats

Soundtrack for April in Paris supplied by SoundCloud

When I do a photo shoot, I try to get more in the spirit of things by playing music from the era I’m showcasing. Below is a playlist from SoundCloud that I listened to while gearing up for my Audrey Hepburn photo shoot. Enjoy!

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  • Thank you so much for the mention! I love that you draw inspiration from eras gone by – you rock them in a totally updated and sophisticated way! Absolutely love those pointed toe flats. It’s definitely tough to be feminine while avoiding looking too cutesy – a daily challenge!

    • Thank you, Laura! I kept thinking about your post about the “cute” word while writing this so I had to share! I think a lot of petite ladies can relate!

  • What a great post—and music to go with it—what a great hostess you are Sherry!!
    It’s too bad you’re not here when I’m reading your post, because then you could hear me laughing at your writing—the fairy godmother was priceless!!
    I have many comments (of course)….
    1-is that you in the first picture holding the fawn? With pink jeans?
    2-This outfit is wonderful—I’m not sure I’d categorize it as “feminine”—just purely stylish—something I’d think to wear on a regular basis!!
    3-I truly love (emphasis on LOVE) the shoes!! I applaud you for not matching them or even going neutral….but adding the pop of red just makes you look quite fabulous!
    4-It’s funny how you said the shoes aren’t the most comfortable—it’ll be interesting to see when they get more wear if they’ll feel better? Of course, anytime we go for a “walk”—I put on my tennies. But comfortable shoes are (IMO) ones that don’t rub or hurt my toes/heel!! I find as I’ve gotten older…that just walking too much (even with my orthodics) makes many areas of my body hurt—ha ha!
    5-I know I’ve said this before, but you are such a great story teller Sherry!!

    • Thank you, Jodie! I am so glad you resonate with my sense of humor, however quirky it may be! 😍

      In answer to your questions:

      1 – I wish that was me with the fawn! You have made my day just by asking! No–that’s Audrey Hepburn! (I’m all atwitter now that someone thought a picture of Audrey Hepburn could be me! Thank you!)

      2 – If you saw how black and gray my closet was before starting this venture, you would see this outfit as feminine. I’ll admit it isn’t boldly feminine. There’s no wasp waist or skirt or dress to point arrows to the femininity, but the colors of this and the simplicity was a leap for me into girlie territory! 😃

      3 & 4- Yes! The shoes (I think) were necessary to elevate the look from pretty polished to extra fab. I’m so glad they worked the way I hoped! As for their comfort — flats have never had the arch support I need. Maybe it’s because I’ve spent years in heels that now, when I wear flats, I feel almost awkward. And they usually make my feet hurt as a result. But like you said, after long periods of standing or walking, my feet aren’t the only things that hurt, no matter what shoes I wear! So I’m getting to the point now where I wear whatever shoes I want, knowing my feet are just going to hurt.

      5 – You have now made my day twice in one comment! Thank you for being such a great support, Jodie!! ❤️

      MUAH!!! 😘

  • Well there is no doubt you look French chic here. Probably moreso that 90% of the French women I often see in Nice where my husband is from.

    The pop of the red in the shoes really does make this a stand out look. I cannot wear flats at all. At all. It makes me sad. They are worse than wearing 4 inch heels, although I cannot wear those either.

    What a great photo to have of your Mom.

    I think it would be interesting to see what a saleswoman from Nordstroms would pull out for me. Ha ha!


    • Wow, Suzanne! What a great compliment! Thank you!

      What is it about flats, do you think, that makes them so hard to wear? Is it because we’re petite and don’t want to be seen as shorter? Is it because they never have good arch support? I’ve been racking my brain trying to understand my aversion to flats, especially after finding a pair I actually like the looks of. But even then, when I put them on, it takes me a moment to be okay with wearing them. It really wasn’t until I saw the photos of this outfit that I believed they could work for me.

      If you ever go to Nordstroms for a personal styling appointment, can you let me know where and when? I’d like to be there to see what she pulls for you. You have such an amazing taste and talent for finding groovy, eclectic things that work perfectly together. Each outfit is a work of art. I can’t imagine a stylist being able to tune into that as well as you already do. Maybe one day, when I’m in your neck of the woods (and I do go there annually), we can connect and you can show me how to do it!

      Actually…would you be up for an interview sometime? You’re in Toronto, right?

  • Ah, Sherry, what can I say?! I so look forward to your posts and this one does not disappoint. I just knew you had a look of Audrey Hepburn about you in your last post. I actually think this look is very feminine – as you say, not frilly and floaty cutesville, but graceful, hinted-at femininity and I think this has a much stronger appeal. I am a huge fan of Audrey Hepburn though and so am won over from the start! The whole look is absolutely charming and suits you down to the ground – Elizabeth Podlesnik certainly knows her stuff.

    Like you, I have always gravitated towards black, navy, cream, jeans, boots – always safe and not necessarily unfeminine but making me blend into the background! I think running these blogs pushes us out of our comfort zones and it is interesting to see how we evolve our styles as we gain confidence.

    Your blog posts are full of interest and there is always something over and above the outfits – this time even a soundtrack! I can’t listen to Moon River, it brings back sad memories for me but it is devastatingly beautiful and Breakfast At Tiffany’s is my favourite film of all time – just thought you should have a picture of yourself with a little guitar at the end there! I read the book too, which is quite different.

    As for flat shoes, if you are going to persevere, then these are the ones to go with – makes it worthwhile, they are fabulous. I struggle to wear flats too, but I think it is partly because of being so small and partly because I just wear heels all the time and have done for decades so feel almost as though I am falling backwards without them! I even wear low heeled mules in the house and round the swimming pool – maybe I need some therapy there! 😀

    This is a bit of a long comment, but before I go, thank you for the Ella Fitzgerald – April In Paris – fantastic – I have just added it to my Spotify list! xx

    • Astrid, thank you for always having such kind and insightful things to say! I do think this blog has pushed me out of my comfort zone and I just want to keep going until I break through and completely embrace fashion as another expression of my creativity and who I am. And how I would LOVE to have Audrey Hepburn’s presence and charm in the process! 🙂

      I think you may have articulated my difficulty wearing flats in general — I almost feel like I’m falling backwards without a little bit of a heel! Thank you for expressing something that I was having a hard time putting to words!

      I’m so sorry to hear that Moon River makes you sad. I won’t push to find out why or to try to change your impression of it. I’m just glad you enjoyed the other song(s). As with pretty much everything I do, I enjoy music from every era and every genre. I hope to create a playlist each time because it’s just one more creative outlet for me.

      Oh! One more thing — Did you enjoy the book better or the movie? 🙂

  • Sherry, I’m curious as to why in the past you equated feminine styles with itchy lace etc… and why your perception of dressing feminine meant uncomfortable and invisible, as those are quite strong perceptions? Isn’t is strange how we view the world sometimes and I wondered why that particular view evolved? You don’t have to answer, I was merely interested!
    This is beautifully feminine outfit. Sleek, streamlined, unfussy but the touches of the scarf and the red shoes add vibrancy in a very eye-catching way.
    Every woman should own a pair of stand out red shoes and you have totally found yours! If you walked past me in the street, I’d wrestle these off you!
    Couldn’t agree more with Laura about that dreaded ‘c’ word for us petites!
    I’m with Gilda all the way- that’s a great quote, thanks for sharing. It made me chuckle as it resonates so much with me. If it’s itches, it’s out!

    P.S. The link to the-bias-cut.com doesn’t work by the way. You’ve done underscores when the words are hyphenated


    • Hi Jacqueline! Your questions are absolutely up my alley and I will be sharing more about the whole itchy lace thing as soon as I can find a lace thing to wear that doesn’t bug me. Let’s just say that I can remember in fairly vivid detail the day my mother forced me to wear an itchy dress — with a cold zipper up the back, no less! It was not a pretty picture.

      My thoughts and perceptions on feminine dressing came (I think) from having grown up in a very conservative home and community in and around Texas. I need to be clear when I say that that I’m not bashing my upbringing or people who live there. Still, the truth was the truth and, even though my mom was a strong, independent woman with a career of her own, when it came to leading the community, it was clear that it was better to be a man. As an example, when my mom decided to go back to university when I was about 5, the women at our church pulled her aside and chastised her for being a horrible mother. She still went to school and, before she retired, she was a highly respected elementary school principal. But even with such an example in my life, the message still seeped in. I can remember wishing as a young girl that I had been born a boy so I could do the things my brother did.

      So, somewhere along the way, I think I started wearing clothes that made me feel more powerful in the masculine sense of that word. They weren’t the lacy, feminine clothes I grew up wearing. Not only did they make me feel stronger, but I felt like they covered me in a way that wasn’t suggestive as well — a way of protecting myself from unwanted advances and such. It wasn’t a conscious decision to go that direction. It’s only been in writing this blog that I became aware of it at all. But I’m having fun rediscovering more feminine style and embracing the strength of the feminine voice at the same time.

      Thank you so much for the note about the link to the-bias-cut.com! It should be fixed now!

      Hope you’re having the best week! I’m off now to check out what you’ve got going on at your blog!

      • Apologies for the delay in replying, Sherry. What an in depth explanation. Thank you so much for sharing. It all makes perfect sense. Our upbringings can certainly affect how we see the world long into adulthood. Such a shame your Mum was chastised and bravo to her that she stood her ground and had the career she did. A great example to you I’m sure. My Mum was also a teacher but she was positively encouraged by my grandparents.
        I like the masculine chic look partly because I was a tomboy growing up – the influence of being the youngest with two older brothers! I had to keep up as they climbed the trees! And I too hated dresses.
        My, my what a lot of common ground between us.

        • I agree, Jacqueline! We have a lot in common! My hope is to get out your way in the next year or so — the sooner the better, as far as I’m concerned — and I’m hopeful that you, Astrid, and I can get together then. If you’re in Seattle, please know you have a guide and a friend at the ready!

  • Such a lovely look. Your right, this look really suits you. The colour of the trousers 👌And what a great idea to contact someone from such a great bran. I would love to have seen the room she had ready for you. I think I might just contact someone myself and have a go at this.