Styleblazers Series

Fashion Through The Decades From Petite Over 40

Sometimes you need to take a few steps backward in order to be able to move forward. Sherry Dryja from Petite Over 40 can attest to that.

Petite fashion bloggers over 40

The Seattle, Washington food writer was stuck in a style rut before she came up with an unusual idea to try on decades of fashion in search of her signature style.  Today Sherry is one of many petite fashion bloggers over 40.  Her specialty? Sherry researches and models iconic fashion looks and then blogs about her discoveries.

Readers love to follow Sherry on her fascinating journey through time, a journey that has helped shape how she dresses today.

I recently got a chance to chat with Sherry about her unique approach to fashion blogging. Here’s my interview with this Fabulous After 40 Styleblazer.   


Petite fashion bloggers over 40

Deb: Take us back to the time you decided to climb out of your fashion rut. Was there a defining moment that made you realize it was time for a change?

Sherry: When I turned 45 I became aware that I was feeling drab and depressed about my appearance. When I looked in the mirror I sed negative changes to my skin and hair. I got really down on myself and realized the only time I ever felt good about how I looked was when I got dressed up, put on makeup, and went to the hairdressers. This made me feel “put together.”

At that time, I didn’t put much effort into how I looked. I work from home, me I encounter other humans besides my husband during the dis when I walk the dog. I guess I had given up caring who saw me because the most effort I made was choosing which hat I’d wear to cover up my hair when I was out in the neighborhood.

It was while visiting the hair salon that it dawned on me that I didn’t have to feel like this, and it was up to me to change things. So, I went home and started dissecting where things had gotten off the rails.

What I found was a sea of black and denim in my closet with loads of tennis shoes and Oxfords. For me, it represented that I had fallen into a rut and needed to do something completely different to dig my way out of it.

Petite fashion bloggers over 40

Deb: On your blog, you play with styles from various periods to find your unique style. What made you take this approach? 

Sherry: My passions are genealogy and history. I love the stories of people and cultures. Fashion is rooted in history. It is influenced by what is happening in the world and, in its own way it influences some of what happens in the world. It’s an expression of an era.

We’re at a place now when all those expressions from the past are mixed and matched into every kind of style out there. It’s a great time to explore because you can wear anything from any era and you’ll find kindred spirits who think it’s great.

The only downside to all that choice is that it can be difficult for someone like me to narrow down her style. I tend to like everything. That’s why I am breaking my search for decades. Not only does it allow me to focus and take “bite-size nibbles,” I can see the progression of a trend from one era to the next. Once I grasp how something was worn in the 1920s, for example, I can see how the same idea is worn today, and then I can try it on for myself in a modern way.

Throughout this process, I am learning a lot about my likes and dislikes. I’ve started to see what I’m drawn to and what I resist. I do try to keep an open mind since this is all about exploring every aspect of fashion to find my signature style. I’ve been surprised to see what I really love and resonate with, and I’ve noticed I have quite an eclectic taste. I don’t know that I will ever be able to say, “This is where I belong” in a specific genre of style, but I do think at the end of this I’ll have a good grasp on what best expresses who I am.

Petite fashion bloggers over 40

Deb: You make wearing vintage clothes a very personal experience. Take us through your fashion evolution starting with your teenage years.

Sherry: As a teen, fashion was about emulating the looks of celebrities I admired, impressing others, and dressing to be taken seriously. At 17, I was often mistaken for a 12-year-old because I was so much smaller than everyone else. I really did look young for my age. This is a blessing today, but back then, I just wanted to be accepted for the age and experience I had.

During this time, I started working at a small-town clothing boutique and Merle Norman makeup studio. The owner took me under her wing and started teaching me how to do makeup and how to dress with quality in mind. Back then I wore the latest fashions available at the boutique where I worked. This included all the features of the 1980s: heavy eye shadow, big hair, high heels, and outfits with bright neon colors.

The idea of dressing to impress and to be taken seriously stayed with me into my 30s. It always felt like someone else’s idea of what I should look like, though. I remember tottering to my classes in grad school in high heels and skirt suits so the older members of the classes would take me more seriously. My confidence was really wrapped up in the brands I wore and the expense I paid, and, to be honest, at the end of the day, that’s not really me.

Today, I want to dress for me, to express who I am from the inside out. When I do genealogy and discover a new story about an old relative, I feel more alive, more real, more connected, and in tune with the bigger picture of humanity. Following a similar line with fashion is having the same effect. It’s helping me express myself as an individual, but it also connects me to ancestors, designers, and fashion icons from times gone by. That is the space where I feel most authentic and creative.


Deb: As you move through time on your blog which period or iconic fashion elements do you relate to the most?

Sherry: I started with the 1920s because I’m drawn to the shapes, fabrics, and glamour of that era. A modern take on the unstructured forms from that period is Eileen Fisher’s line of clothes. I’ve been buying her clothes for years now. They’re a little more sedate than the beaded and fringed bling of the 1920s, but the quality of fabrics, the unstructured shapes, and the way the outfits hang are reminiscent of the trends of that day. I will likely always love the look, feel, and comfort of Eileen Fisher and others who draw on the 1920s as a muse for their designs.

Having said that, as I move forward into the 1930s and as I explore my curiosity about more feminine apparel, I have discovered a love of color and pattern I didn’t know I had. I’m eager to see how this plays out going forward and whether I will, at the end of all of this, prefer more structured clothes with ruffles, lace, and prints.


Deb: You have a few posts about Coco Channel. What have you learned from studying her style that you have incorporated into your own?

Sherry: My love and admiration of Coco Chanel’s influence on fashion grow every day. She had a way of taking simple pieces and elevating them to elegance by just adding a belt or a long-strand necklace. Nothing she did was fussy.

Comfort was a high priority for Chanel, but her comfort didn’t involve yoga pants or jeans. With a broad stroke, her early style could be painted simply as “skirts, jersey tees, and pearls.” That simplification doesn’t take in the quality of what she was wearing. Her fabrics always draped nicely off her shoulders and hips, giving her a sophisticated look no matter what she was wearing. Her outfits were never sloppy, nor were they too tight.

Her foundation – top and bottom – was always simple, but she changed the look of it by adding “a third piece”: a belt at the hips or waist or, more likely, several strands of pearls and costume jewelry mixed.

From all of this, I see the value of quality fabrics and craftsmanship, the versatility of simple pieces, and the importance of finding the right fit, even if it has to be altered.


Deb: Do you have any other fashion icons who inspire you?

Sherry: I have always loved the style and elegance of Audrey Hepburn. She dressed simply, and yet we all know her classic look – capris with flats and an understated top.

Besides Coco Chanel and Audrey Hepburn, I am inspired by the ideal of the “Parisian woman.” I realize it is an ideal and a generalization to say that all Parisian women dress with ease and elegance, but in my mind, they epitomize the same sort of simplicity and beauty that I admire in Chanel and Audrey Hepburn.


Deb: You’re very petite. Tell us about what challenges present when dressing and shopping for clothes and how you get around that?

Sherry: It’s well known that petites struggle to find the right length on pants and sleeves. I go into shopping knowing that I will likely have something altered. Thankfully, a lot of big stores these days have a line of Petites, so that makes it a little easier.

My biggest challenge, if I stick to shopping only in Petites, is the selection — it is far less colorful and vibrant than what you might find in regular departments. One of the reasons my closet was so full of black when I started coming out of my rut is because black is one of the most available colors in Petites, especially in skirts, dresses, and pants.

Since starting this journey, I have spent more time exploring regular sizes with the idea that I would just have everything altered. I’ve been pleasantly surprised to discover that it’s become a little easier for Petites to find a good fit in regular sizes without very many alterations thanks to the advent of the skinny pant, the popularity of ankle pants, and the plurality of short skirts/dresses. On taller women, those things might fall above the ankle or above the knee, but on me, they look like they were made for my frame, hitting at the perfect spot near the top of my foot and just at the knee. I still have to get jackets and the arms of dresses altered, but it’s so nice not to have to get everything hemmed. And, even if I did have to do all that, the look of a great fit is totally worth it.


Deb: You recently wrote about the ageless appeal of pearls. What other fashion items do you think have ageless appeal and should be a part of a modern woman’s wardrobe?

Sherry: Because every woman has their own connection to style, it’s hard for me to be very specific on items. Generally, I recommend that a modern woman have a really great fit in everything she wears, including a good-fitting bra and undies that are not visible beneath pants and skirts. These things help set the shape for everything else and, if they fit well, there’s no fussing with them later.

Beyond that, I think it’s key that modern women have at least one complete outfit that makes them feel beautiful, no matter what the style. To me, this means it fits well – not too loose, not too tight. Even if it’s unstructured by nature, the fit should be proportional to a woman’s body. Too much fabric can make a person look larger than she is. And too tight – do I need to describe how that is unflattering?

You might say, then, that knowing a good seamstress or tailor is my recommended “ageless accessory.” If you know how to sew and can alter your own clothes, God bless you – and can you come to my house and teach me how to do that?


Deb: Let’s talk color. What are your thoughts on color, and which ones do you find yourself drawn to?

Sherry:  Before I started this journey my wardrobe consisted of a lot of blacks. Black is a classic color, but it is the color most available in petite departments. To try to break my reliance on black, I have made a pact with myself not to buy anything in that color while I’m “traveling through time” for my blog posts. Now that it’s spring finding color has become a lot easier!

What I’ve discovered is how color and patterns can give just a little extra spice to an outfit. Me, blue is my favorite color. I feel like it brings out my eyes. I have to be careful, though, because the blue can go very dark and becomes almost as neutral as black. I try to stick to lighter blues, then, and this forces me to try different colors that work well with that, like lipstick red, baby pink, and even yellow, a color I would never have tried before.

Beyond blue, I’ve really gotten into the army greens this season. It works very much like a neutral and can be paired up with any number of colors very easily. It can be dressed up or down, depending on the style or cut of the piece. That versatility makes it a winner in my book.


Deb: What are the most interesting things you learned about having great style since researching fashion through the decades?

Sherry: 1) Fit is as important as anything else for having a great style. No matter what it is, if it fits well, chances are you won’t be fussing with it, and it’ll look like a million bucks, even if you only spent a few dollars on it. Getting the perfect fit generally involves going to the store and trying things on, possibly working with a trusted friend or a stylist to get honest opinions about how things are fitting. And then, if necessary, get the outfit altered to make sure it fits perfectly.
2)Everybody can look beautiful in the right shapes and colors, so keep an open mind, have some patience, and set aside some time to discover what works best for your body by trying things on—even things you might resist initially.

As an example, I’ve learned from trying things on that empire waists and wrap dresses tend not to look great on my body. Although fit and flare dresses, look fantastic, I feel like a movie star in them! I would never have tried this style of dress before, and that’s kind of a shame because I spent so many years avoiding them when I could have been feeling fabulous! Once you find flattering shapes, look at the color and see what brings out your favorite features – your eyes, skin, hair, etc.

3) Keep it simple with the Rule of the Third Piece: Armed with a good-fitting, perfectly shaped outfit, pick out a simple third piece, such as a necklace, a scarf, a jacket, or a belt. It doesn’t need to be fancy or overdone – unless you want that – and you don’t need more than that third piece to make the outfit complete.


Deb: Anything else you would like to add?

Sherry: I would like to add that the over-40 blogging community has been an incredible inspiration and support on this journey through fashion history. If I had the fourth tip to give your readers, it would be to hook up with friends or create your own style “support group” in your town. ( would be a good place to look for something like this.) Having others to bounce ideas off, discover resources, and explore fashion with an open mind helped me.

Deb: Thank you, Sherry, for taking us back in time to see how fashion through the decades has inspired you. Ladies, be sure to visit Sherry’s blog, Petite Over 40, where you’ll find more vintage fashion and fabulous finds.


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4 thoughts on “Fashion Through The Decades From Petite Over 40

  1. This piece is so great!! As a petite woman in her 50s and a jewelry maker, I started following Sherry on Instagram for style ideas. Like, who wants to look frumpy? But I also didn’t want to look like I was unwilling to give up my 20s! Anyway, thank you for this great article!
    Looking forward to following you as well! All my best to you, Margie

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