Is it frivolous to think about getting dressed up during these chaotic times? I don’t think so. Getting dressed up is a slice of creative, energizing fun, and it’s a power move. A woman who puts thought and energy into how she presents herself is choosing to show up as a full participant in life and claim the right to be seen. After 60, when many women begin to feel invisible, dressing up demonstrates confidence, self-esteem and individuality. But, given the weight society puts on women’s appearances, It can also be stressful.
To explore this issue, I asked a handful of my stylish friends, all over 60, their strategies for getting dressed up and how they feel about it. I found their answers fascinating, and think you will too.
What do you get dressed up for?
My friends have different interpretations of what getting “dressed up” means. Some think only formal occasions like weddings or benefits require dressing up. They rely on a go-to uniform for the rest of their activities. Others see a simple lunch with girlfriends as an opportunity to look special.
Linda, from Florida, says, “I’ll dress up a little bit even if it’s a casual get together. I just feel my best whenever I look my best.” Maureen, who splits time between Mexico and Chicago, agrees. “I get dressed up for almost every social occasion, be it a family birthday party, dinner with my husband, a concert at Millennium Park, or a big event. Why not feel pretty?”
Another Florida friend, Marlene, enjoys getting dressed up regardless of where she’s going. “I actually get dressed up for most occasions,” she says, “from tennis to an elegant dinner out and everything in between, including doctors’ appointments. I’m usually always thinking about what I’m planning on wearing.” I call Marlene my “style and aging role model” because at 77, she always looks amazing and exudes positivity, as you can see.
Some of my Chicago friends feel like they have fewer opportunities to dress up than when they were younger. As a leadership consultant, Tricia dresses quite formally for work, wearing tailored suits and dresses. But she misses having more fancy social events on her calendar. “I love getting dressed up for a wedding or the holidays, but outside of work, I’m often in athleisure. I wish I had more dressy occasions. We don’t go out very often and I miss dressing socially. Younger moms seem to be dressing up more.”
Midge, a stylist with a long career in retail on Chicago’s North Shore, agrees. “Twenty years ago there more parties to go to, club events and dinners, etc. Not anymore, and I don’t mind it at all. Now, truly getting dressed up is a bit of a chore, even though I know what I like and what looks good on me. It just happens so infrequently now.”
What women wear definitely depends on the climate and vibe of the place they live. For example, in Florida we wear a lot more color than women tend to wear in Chicago. My blogging bestie Laura splits her time between Park City, Utah and Brooklyn, New York. She says, “Dressing up is radically different based on location,” she says. “In Park City, anything that’s not athletic wear is dressy. Locals don’t want to be mistaken for visitors, many of whom try too hard for the Western look (through an LA lens) when really the vibe here is much more ski bum. Dark jeans and a cashmere sweater is dressed up.” Dressing up in New York is a different story.
How do you feel about dressing up?
All the women I interviewed have great style. However, dressing up doesn’t come easily to everyone. Patty dreads it. She has a fresh, classic wardrobe she wears confidently in her everyday life, but dressing for formal occasions makes her anxious. “Dressing up means panic,” she says. ” I don’t know how to interpret the dress codes—what’s expected. My insecurity comes out and I’m not sure if I’ll do it correctly. As a younger woman I wouldn’t do things because I’d fear I’d be dressed “wrong”. I care less at this age. I’m still stressed out, but I have the confidence to participate. I go.”
Patty might feel better when she hears what Midge has to say about dress codes. “As someone who works in retail I shout it from the rooftops—there are NO rules, none, as to what constitutes even formal dress. “Black Tie” has a wishy washy personal definition for most women; if you want to wear a pantsuit, by all means! Short versus long, it’s up to you. Truly, it is a menagerie of styles and is driven solely by what is comfortable and how it makes you feel. Frankly, if you hate what you are wearing it shows in how you carry yourself. Flipside? Loving your look gives you pep in your step and lets you ooze confidence.”
Dressing up makes Tricia anticipate the event and feel more confident and outgoing. “When I like my outfit, I feel energetic and enthusiastic about the night, I’m more social. Getting ready is an indicator of a fun night ahead—meeting new people and having interesting conversations,” she says.
Maureen says, “I LOVE getting dressed up. It is one of the few ways that I feel I can truly express who I really am.”
Berit, from Minneapolis and a frequent contributor here, is a true fashionista. She considers getting dressed up an endless source of creativity and a way to fully celebrate life. “I think half the fun in going to parties or events lies in finding the perfect outfit to match the occasion,” she says. “Having opportunities to dress up is an occasion to try to look extra “good” and to go beyond the ordinary/mundane. During Covid, It was really quite debilitating mentally to not have anything to look forward to, to dress for.” She also sees travel as an opportunity to experiment with different styles and trends and constantly looks for new inspiration. Here’s a chic, sheer outfit she wore to dinner out in Manhattan, based on a similar outfit she saw on Instagram.
Dressing up is also a way Berit to navigates an unpredictable world. “I know that I can control how I look by what I wear and how I present myself,” she says, “but I cannot control a lot else about how the day might unfold. It’s one of the only things in this life that I can control.”
What makes you know you’ve nailed your look?
My friends agree, comfort is the number one ingredient to feeling good. This can mean the fit of the garment or fitting in with the crowd. Linda says, “When something fits well, I feel great in it. I often rely on a tailor to help me get just the right fit. Fabrics mean a lot. I need something that moves easily with me and isn’t scratchy. I feel best in pieces that are just a tad loose. I want to be able to dance!”
When Laura attends formal events in New York, she strives to look put together but not too flashy. “I would say I feel my best when I’ve correctly guessed the level of dressiness for the place and occasion and hit the sweet spot. I always want to look like me (versus feeling like I put on a costume) but I think there are ways to do that and still be in the vibe of the event.” She usually gravitates toward quieter looks, but felt perfect in this stunning color-blocked Stella McCartney dress at a gala last year.
However you interpret it, feeling comfortable allows you to relax and enjoy the fun of the event without feeling self-conscious—which is the point. As Patty says, “The most important thing is that I feel comfortable in what I’m wearing. At my kids’ weddings I felt so good in what I wore, it was life changing. That’s my goal, to feel good in what I’m wearing. Fit, comfort, fits the level of the occasion. I fit in where I should be. It’s the best feeling in the world.”
The way we dress is a form of communication, both to others and to ourselves. “I am communicating that I love myself and love taking the time to look put together and well dressed,” says Marlene. ‘When I was a little girl, I was looking in the mirror at myself, all dressed up. I was turning around and saying that I looked pretty. My mother told me not to be vain. It took me quite a while to overcome that comment and learn that it is all right to look at yourself and love what you see!”
More Ideas and Insights From My Friends
When it comes to putting together a look, my stylish friends have some wonderful insights. Here are things that work for them, based on their unique perspectives. Maybe they’ll inspire you to try something new the next time you dress up!
“I have a wide smile so I love to wear bright lipstick to accentuate it and communicate my boldness. And, once dressed, I always add one MORE piece of jewelry. It’s a tip I’ve used for years.” Maureen
“Honestly, I’d rather be a little overdressed than underdressed.” Patty
“I’m most comfortable in classic styles maybe with a little twist or flair. That said, I love to get complimented on my outfit by both friends and strangers alike. For me it’s an esteem builder and also nod to my creativity.” Berit
“Accessories are important. I love jewelry. It doesn’t have to be expensive jewelry or a lot of jewelry, but just adding some pieces to the outfit changes the whole look. I also pay attention to my shoes and handbags. I will change handbags with every outfit when I feel it improves the overall look. And I love shoes!” Marlene
“What I communicate with how I typically dress is understated luxury. Nothing too loud, not many prints. I do the same thing when I dress up. No drastic style changes from one to the other. This is a choice, not because I want to be ‘silent’ in my clothing selections. I just know what I like and what looks best on me.” Midge
“I feel confident when I am dressed up! I go for something that fits well and is flattering and age appropriate. And I don’t want to forget the shoes, purse, earrings. I love picking those out and putting them together for the perfect event.” Linda
“A jacket is an essential piece, I often wear one. I love scarves too—the color, along with the my nice jewelry, adds polish and softens my neckline. I know I’ve nailed an outfit when my husband lights up when I walk down the stairs. And when a girlfriend compliments my outfit, I feel really good. I’d gladly take a few catcalls! Tricia
“In New York, I strive to look put together, but definitely not like I’m trying too hard. Too much bling or obvious logos are a no. I tend to play it safe and wear a lot of black, navy, gray and white.” Laura
“I grew up in Miami, wearing a lot of color, and still love it! Color makes me feel happy and vibrant.” Marlene
My Final Take on Dressing Up
I can’t thank my friends enough for contributing to this story. This group of women is a tiny subset of society, but talking with them has shown me what a personal, expressive, optimistic endeavor getting dressed up is. I fully embrace Midge’s “There are no rules!” proclamation. When we dress for a special occasion, whether that’s casual lunch or a gala, we make choices about who we are and what we want to communicate to others and ourselves. It can be hard to find items of clothing that reflect our individuality (and still fit well and feel comfortable). It can be hard not to be critical of our bodies and appearance. It can be hard to put ourselves out there and attract attention. But I say, let’s go for it! At our age, what do we have to lose ? And especially during dark times, the world needs us at our best, brightest and most UP possible.
Of course I’d love to hear from you on this topic! Drop a comment here or on my Instagram page. I’ll leave you with a few more dressed up pics, just for fun.
Fully Fabulous 
Love this article!! It’s fascinating to see all of the different opinions of getting dressed up. Thanks for including me!Marlene Sent from my iPhone
LikeLike