The Importance Of What You Wear In Midlife And Why It Matters
Do clothes make the woman? Some would argue that what we wear is unimportant and our interest in discussing fashion is shallow. Attempting to trivialize the fashion struggles of women over 50 is not only uninformed but also naive because what we wear can make or break our confidence, which makes it worthy of discussion.

We have lots of new readers, so I’m republishing a post that many of you may not have read. I think it’s an important topic that needs to be discussed.
Clothes can be a shield we use to get through challenging times, but more importantly, they tell the world who we are. Whether we like it or not, we’re judged by our appearance, and the clothes we wear matter.
Look sloppy, and people may decide you’re careless and have little respect for details or yourself. Wear overly revealing clothes, and you may be seen as inappropriate or desperate. Wear flamboyant colors and you may be seen as carefree or loud. The upshot is that we are judged by our appearance so managing our image is important.

Women over 50 often struggle with feeling invisible. How we dress is a powerful tool to combat that lack of visibility by restoring our feelings of power and control.
Our generation has a challenge with fashion that earlier ones didn’t. My grandmother never struggled with what to put on in the morning. She wore her printed house dresses at home and dressed up to leave the house. There was no question about whether she should wear a T-shirt and jeans or a dress with stockings and sensible shoes. There were fewer options because there were unspoken rules.

Our generation doesn’t want to follow fashion rules unless they can use them as tools to dress with confidence. We want to make our own choices and dress to express ourselves. This freedom is welcome, but it can also leave many women unsure about what’s appropriate. With so many options to choose from, she needs a clear vision of the message she wants her clothes to send.
An open discussion about fashion and image is helpful for many women over 50. Does that make us frivolous? No, it makes us curious, intelligent women. To imply these conversations are unnecessary is to belittle the struggle many women face each morning.
Have you ever felt invisible? I’d love to hear your thoughts. What are you struggling with?

A woman in the grocery store approached me and complimented me on my outfit. After I thanked her, she said “do you always dress up to go to the grocery store?” ( I was wearing colored jeans with a coordinating top and a fun jacket.) I was not dressed up in my mind, that was just the outfit I’d put together for that day. I find my clothes are a creative expression, and I enjoy putting an outfit together. Comfort is more important to me now, but that doesn’t need to mean boring. Fashion, for me, is just fun. And it really does help one feel more self confident.
Yes, yes, yes, I agree! I do dress up for my day which always helps me feel better than if I just haul on any old thing.
I started life as an aspiring artist who loved color. In college, I realized that the only thing I lacked was talent! And I also realized that decorating myself was the way that I could express how I felt about color and texture and arts in general. Clothing and jewelry have always pleased me and I have always loved playing with them. I dress to please myself and say that if one considers clothes frivolous, GOOD…frivolity needs to be part of life (which is serious enough). I am in my early 80s and have never felt invisible, though maybe I should have. Iris Apfel has always been a beacon tho far beyond me. Two of us recently agreed that we would assemble fun dressy outfits and go out for high tea as a way of finding some pleasure in scary times. You are absolutely correct in your assessments of the role of clothes and appearance.
I love your comment, thanks for sharing Lee!
Oh how I needed to read this. I enjoy just trying to dress nice and have that confidence. Sometimes I feel like my peers do think it is frivolous (not being being extravagant, just enjoying fashion and style) but I am also so much more productive at work when I have that confidant feeling! Thank you for all you do.
I have found the opposite here in North Texas. If I walk into a store, they are very welcoming to me, and ask if I need anything. I dress like I care about how I look, thanks to your blog, {smile.}. They have figured out, If you dress well , that maybe you will buy something from them. The young people here do not seem to dress well. They wear athletic wear mostly.
I haven’t experienced anyone ignoring me here. We do have a lot of young people who live here. This city north of Dallas is a very family community, and friendly.
I am sorry this woman feels the way she does, but she doesn’t have to join the blog. It is her opinion, and we can agree to disagree. It is all good and we can still get along with each other despite our differences.
I agree with everything you said, with one caveat! For the woman who struggles to put food on the table, or a roof over her head, fashion is frivolous. It is all about perspective, or where it fits on one’s hierarchy of needs! For those of us who are fortunate enough to have basic needs taken care of, fashion can effect our mood, our confidence, how other people perceive us, and often allow us to make a statement about ourselves and our beliefs.
Thank you for this blog, it is a bright spot in my day!
That’s a very insightful thought, thank you. Many of us are so blessed, we forget. For woman who are struggling like this, self-care and a small amount of time with our appearance (using what we own) will boost confidence and help her feel more empowered.
I just had a woman at my desk yesterday purchasing some insurance. She had a wonderful short hair cut with a long sweeping curly bang (she was embracing her gray) and the most funky glasses and I complemented her on her glasses. She mentioned what local shop she got them and how the woman there looks at you when you sit down and says “I know exactly the glasses for you!” We need more retailers who help empower us!
Yes! Rather than just sell us the frumpy looking clothes they have in stock.
Thank you for this post Jennifer! I read your blog every day and this one makes me smile. I’m on the way to the airport in my Frank and Eileen shirt, Everlane jeans, comfy sneakers, and thanks to you I added 2 stacked necklaces, and a bracelet. I’m 72 and feel stylish!
Awesome, your outfit sounds modern, stylish and comfy! Have a fabulous flight.
Hi, Jennifer. I love fashion and putting together outfits for myself is one of the pleasures of my life. Since this is what makes me happy (along with many other things), I will continue to do it with gusto! And your blog is a pleasure to read. Have a wonderful day.
I wholeheartedly agree! I’ve just turned 75 (yikes!) and am really small. That makes 2 strikes in terms of invisibility! But when I’m thoughtful about my outfits, , adding a scarf or an interesting necklace, I feel confident and am treated with consideration . It makes so much of a difference! I’ve begun to wear slightly brighter lipstick which seems to brighten my face! I learned that one from you, Jennifer! Keep the information coming. I like feeling current, not trendy and your blog is invaluable!
Happy Birthday Susan!! That’s a fabulous milestone. I’m so glad you’re here sharing with us too.
Thank you Jennifer, and all who have commented on your post! Great information and so true. What we wear reflects who we are and how we feel about ourselves. Wishing all a wonderful day!!
I struggle a lot with not dressing like my daughter- nor my mom. I want to be fashionable and confident. I so appreciate your blogs! Thanks you!!
Thank you for sharing Lenora. Many brands don’t make it easy for us and some “midlife” brands can lead us the wrong way. We’ll chat about this more.
Gen X has entered the chat…as a generation we have always been ignored! That’s why we do what we want and don’t give a “f” what anyone thinks. To me fashion is self expression as much as any other art form. How can something that builds confidence and joy be frivolous? Haterz gon hate.
As someone who is about the same age as you and also has thinning hair I find your blog invaluable. Incorporating your advice has done wonders for me. When my hair, makeup and clothing looks good it is a tremendous confidence boost. You are like having a best friend who keeps you from making those style mistakes.
I’m so glad we have this community to support each other!
If I get up, get dressed and put together, I am motivated to do things. Since I retired 18 months ago, I still get dressed every day. Now my fashion fun is repurposing my beautiful items in a more casual way. I refuse to be invisible; my skin, hair, and body are aging but I refuse to not use my mind and assets to enjoy life. I am more put together now than I was in my earlier years.
Thanks Nyla. I refuse to be invisible too.
At 76 I love you4 blog. Love,Love DRD
I took the “Look Good, Feel Better” class offered to cancer patients, and updated my look, after a cancer diagnosis. It makes a huge difference in well-being and confidence. It has sparked an entire transformation. I have just lost 45 pounds and am now slim and trim. I love taking the time to look “pulled together”, no matter what the occasion. And I am still constantly receiving compliments, even from the young men at Starbucks! Learning how to style outfits from bloggers like you has made getting dressed simple. It’s an art to look tasteful, and brings joy and beauty both to myself and others. I am now 70, six years cancer-free, and loving life.
Bravo HB! That’s wonderful
At 76 I love your blog. Love,love DRD
Wonderful post and discussion. I couldn’t agree with you more! Thanks for being there for us.
Thank you for being here Mary.
I am happy to join this choir, singing about the importance of what we wear, both to boost our confidence and to show that we recognize the importance of events we go to, people we meet.
When my three children were small, I felt invisible. I was often praised as a “good mom, they’re lucky to have you,” which felt like I’d been sent from an agency. Why didn’t I take an hour every now and then to buy clothes that fit better, or get a good haircut? It seemed frivolous, but it would have done wonderful things for my sense of self.
As they got older, I reclaimed style. Usually I’m casual, accenting jeans with bright thrift shop finds. I read AWSL regularly and so appreciate your discussion of principles of dressing — proportion, color — and yes, why it’s important.
Thanks for being here, Margaret
So many thoughts on this post, Jennifer. I remember the moment that I reconnected with the power of a fashionable presence and how it ignited this passion I have for making an effort in my appearance. I went to a YSL retrospective at the Denver Art Museum. The beauty and artistry of those clothes just inspired me. So to me, this “frivolous” attention to appearance has two components…..sharing beauty and not being invisible. The second one has become mote important lately as I crested 60 in the professional workforce. You better believe that when I have an important meeting, I suit up with my best foot forward. Plus, it’s just a lot of fun!
It is beauty and a ton of fun. Bravo Cynthia!!