With the advent of Casual Friday, an earth-shifting change occurred in the way we dress. Casual Friday as a concept gradually creeped out of the workplace and into everyday clothing choices. Comfort became the #1 priority. Is comfort a bad thing? ABSOLUTELY NOT! But somewhere along the line, comfort stabbed style violently in the back, and we were left with t-shirts and jeans…or even worse, the appearance of pajama pants in public! The horror! This article is about how to be comfortable and fabulously stylish AT THE SAME TIME. It is possible to elevate your style without sacrificing comfort. And when you do this, you will almost always be accused of overdressing, which, as we will learn, is just a sad testament to the raging epidemic of underdressing in our society. These days, if you wear a dress, you’re automatically “dressed up.” Ugh! I was raised by a woman who would not leave the house without “her face on” and being “fixed up.” She had “house clothes” and “going out” clothes. And by “going out,” we’re not talking cocktail parties…we’re talking going out of the house. She had high standards for herself. For example, she was appalled at how people dressed to take flights: “In my day, flying was special and we dressed accordingly.” In present-day times, comfort rules EVERYthing. And that, in itself, is not the problem. I live for comfort. My nickname is The Queen of Relaxistan. I am 1000% here for comfortable clothes (see my article about tags and how much I hate them). But mainstream fashion designers got really lazy after the advent of Casual Friday, and comfort got saddled with FUGLY. Let’s look at some brief highlights of 20th century women’s fashion history to try and unravel how this happened, and then well talk about ways you can be comfortable AND dressed.

1910s: Fashion Loosens Up

Gabrielle “Coco” Chanel wearing her striped Sailor’s jersey knit top and pants, 1928 (Wikipedia)

Coco Chanel revolutionized women’s fashion in the 1910s. She removed boning and dismissed corsets and bustles. She introduced us to the wonderful world of jersey, a soft, non-itchy, flowing knit fabric. She simplified the silhouettes and encouraged the wearing of PANTS. The fashion world was completely shocked. And inspired. Women’s clothing became less restricting, more freeing, and women ate it up with a spoon. The loose silhouettes of the 1920s owe much to Chanel and her lesser-known contemporary/rival, Paul Poiret. The fashion trends of the 1920s, all using significantly less fabric than their fussy predecessors, turned out to be perfectly timed for the forthcoming Great Depression and World War II with massive fabric and notion rationing.

1950s: Constricting Fashion Makes a Comeback

A Christian Dior dress from 1954 (Wikipedia)

Then came Dior in the late 1940s and 1950s, who (in Chanel’s opinion), took women’s fashion back several decades. Dior’s New Look used LOADS of fabric: extremely full skirts, lots of pleats, folds and ruffles, and very constricting wasp-waists, tight bodices, and tight sleeves. After years of drab Depression and WWII rations, women flocked to this style, which was repeatedly copied in haute couture and mainstream fashion. Women were voluntarily girdling and cinching themselves again. Chanel was pissed, and her fashion house took a nosedive in the 1950s. Enter the stereotypical 1950s housewife, cleaning house in heels, full skirts, and pearls. It stuck around until the 1960s, when fashion once again revolutionized, and everything became looser and more streamlined again. Caftans, tent dresses, a-lines, and tunics became de riguer, and they never really left us.

1980s: Casual Friday Rings the Death Knell for Style

In the 1980s, Casual Friday became A Thing. At long last, people could cut loose and wear jeans or khakis on Friday, and ditch the pantyhose and business-wear. Unfortunately, people took this a little too literally, Casual Friday gradually became Casual Monday-Friday without us even noticing, but the fashion industry was listening, and they began churning out fugly, design-less clothes by the factoryload. And we accepted it gladly. Quickly, Casual Monday-Friday leaked into our attitude about dressing in general. As a society, we collectively thumbed our noses at the notion of “dressing up.” Sweatpants, jeans, and t-shirts became the American wardrobe of choice. Now, even a casual dress or skirt, or literally anything that isn’t a t-shirt, jeans, or sweatpants, is considered “dressed up.” We at Eccentric Dames Society reject this idea.

Older women are “supposed” to fade into the background

Nuh-uh. No way. Have you shopped a “women’s department” lately? BORRRRRING! Dull shirts, shapeless pants and dresses, all designed to keep you quiet and in the background where no one has to pay any attention to you, like a nice older lady. Admittedly, things are getting better. Thanks to Ari Seth Cohen and Advanced Style, and hundreds of thousands of bold women everywhere, the fashion industry is finally starting to wake up and realize that we still want to look cool, dammit.

Compliments: learn to take them, even the backhanded ones

For some of us, it can be really hard to take a compliment. A lot of women respond to compliments with something like “Oh, this old thing?” or “I got it on sale!”…instead of just saying “thank you,” we voluntarily diminish ourselves. We need to stop that! Just say “thank you” and go on about your day! You don’t have to explain anything to anyone.

Stylish women are brave women

Why brave? I’m glad you asked. Because in a world where we have to face a barrage of undesired attention, wearing clothing and accessories that are outside of the norm brings even more attention to you. If you dress boldly, people will notice. And since people can’t keep their opinions to themselves these days, they will share them — vocally — with you, right to your face. We have to add tools to our arsenal on how to deal with this.

NICE things people will say to you and how to deal with it

It’s not all gloom and doom out there. Most people will really love and appreciate your flamboyant style! And delivering a mutual compliment is a great way to pay it forward.

  1. “I just love your style!” (Thank you, I like yours, too!)
  2. “Wow, you’re really dressed up!” (Thank you!)
  3. “Are you going to a party?” (No, this is just how I dress! or “No, but I’m always up for a good party!” Caution: this may bring forth an unwanted actual invitation!)
  4. “You look beautiful!” (Thank you!)
  5. “Where’d you get that ____?” (If you want, tell them; if you’re like me, I like to keep it private, so I usually just say, “I couldn’t tell you. I’ve been collecting for a long time.”
  6. “I love your sunglasses!” (Thank you!)
  7. “I could never pull that off!” (You’ll never know until you try!)

We had feedback from our Instagram from followers like this: “Dressing like that…you just make people smile!” “You are wonderful! Thank you for living your life!” “Oh wow, you look like you just stepped off a movie set!” Now those are some glorious compliments!

Clueless/dumb things people will say to you and how to deal with it

But then there are the jerks. The ones who can’t keep their traps shut. The ones who never learned, “If you can’t say something nice, say nothing at all.”

  1. “WHY are you so dressed up?” (I like looking nice! Thanks!)
  2. “Where’s the costume party?” (I wasn’t aware of one. Maybe I should find it and crash it!)
  3. “That looks like a lot of work.” (It is. Thank you for noticing!)
  4. “That doesn’t match!” (Define “match.”)
  5. “[Confused looks, straight up staring]” (Ignore)
  6. “[Laughter]” (In this case, I usually just deliver a smoldering glare or ignore it).

This hat (which is fun and makes me instantly happy) caused a woman to burst out in RUDE laughter at me at the pool recently. Shrugs.

Speaking of laughter, I wore the hat on the right to the neighborhood pool at my 55+ community. Another woman saw me, said “Nice hat,” and then burst out into maniacal, hysterical laughter. This isn’t the first time I’ve dealt with laughter, but it was definitely the rudest. Seriously, why do other people’s outfit choices bring out the worst in people sometimes? We aren’t hurting anyone. We’re expressing our style in a world that can be pretty stereotypical and homogeneous. That’s something that should be celebrated! But society isn’t always equipped to deal with square pegs, and we aren’t willing to edit ourselves to fit their world views. So go forth, be fabulous, wear a feather boa to the grocery store. If you aren’t usually a bold dresser, take baby steps. Start with a bold piece of jewelry or a hat. Buy yourself a caftan and enter the amazing world of stylish comfort (shop our selection of caftans here!). It really starts snowballing once you get started! You might need your Invisible Cloak of Dignity sometimes to deal with the newfound attention you’ll be getting; but whatever you do, don’t stop being YOU! And remember: you aren’t overdressed: everyone else is underdressed. Where’s the party? Wherever you go, darling…wherever you go.

by Stacie Herndon

Stacie is a writer, graphic designer, and web developer. Legend has it that she was born old. She has always loved outrageous older ladies, often befriending them over people her own age. She is a devoted Francophile, loves a good Sauvignon Blanc and can mix a mean cocktail. She will have red hair until the day she departs this earth.