Why I’d Rather Be Overdressed (Every Time)
Happy Monday, ladies. I hope you had a wonderful weekend. Mine was uneventful and rather quiet, with load after load of laundry and several hours of ironing, which, truthfully, I find relaxing and rewarding. I know, weird. Today, I’m musing about the act of putting ourselves together as a powerful form of self-care.
Dressing as Self-care
Last week, I ran into Whole Foods to grab some organic raspberries. Just a quick midday errand, nothing fancy. I was wearing a crisp white shirt, medium-wash straight-leg jeans, and a pair of flats I’ve had forever. I carried a crossbody to be hands-free and wore my favorite silver hoops and a fun vintage brooch.
It certainly wasn’t anything flashy but I did feel pulled together. I was surpised when several people commented on how nice I looked. Compliments always feel good which got me thinking about overdressing and underdressing and why I always err on the dressed-up side of things.
Truthfully, I think I got this tendency from my mom. Every morning, without fail, she got up and took out the brush rollers she’d slept in (remember those torture devices?), got dressed, then as she liked to say, “put on her face.” She believed in presenting herself well, even if the only one seeing her was the mailman. I watched that growing up, and I think it quietly took root, not as pressure but as self-care.
That’s the thing about getting dressed…it’s never just about clothes. It’s about care and dignity. It signals that today matters, and I matter. And in a world that seems to be sliding into anything-goes territory, I’ve found I feel better when I make the effort.
Why This Matters
Getting dressed with care isn’t about being fancy or impressing anyone. It’s a quiet way to care for yourself. It can lift your mood, bring structure to the day, and remind you that you’re worth a little effort…even when no one else sees it.
Applying This to Your Wardrobe
- Keep a few easy, polished outfits on standby.
- Choose real clothes and things that make you feel like yourself, not invisible.
- Add an accessory or two that you love, even on your quiet days, especially on quiet days. You may also enjoy How to Feel More Put Together in Under 10 Minutes
I realize that, for me, this is part of living a well-styled life.
Did someone in your life model this kind of everyday care? Or have you discovered it for yourself along the way? I’d love to hear how you use personal style as a way to feel like you.
Digital Detox
Over the weekend, I went on a little digital detox. Not from social media entirely but from the mountain of influencer emails and Instagram accounts that constantly shout about new arrivals, the latest drop, or the one piece you need to own that will make every outfit look perfect. I unsubscribed from a bunch of them, and it felt oddly rebellious… like throwing a catalog in the recycling bin before flipping through it.🤣
The truth is, all that consuming was starting to confuse my personal style. The more I looked, the more I added. The more I added, the less connected I felt to any of it. I wasn’t building a wardrobe…I was just reacting and exercising my add-to-cart finger. The whole thing suddenly felt overwhelming and stressful. It made me focus on lack rather than abundance, which isn’t good for anyone’s state of mind. It drove me into my closet for a cleanout again, and I was slightly shocked at the clothes hanging there that were not my style!
Obviously, I do share links here on A Well Styled Life. It’s part of how I support this blog and keep it going. If I find something I love and think might work for you, too, I’ll share it. I also enjoy curating outfit collages that may ring your sartorial bell. But I never want to be that person who encourages overconsumption or makes you feel like you need to keep shopping to have great style. That’s not what this space is about.
What I really hope to do is help you rediscover, refine, or simply feel more at home in your own style. To help you dress in a way that feels authentic, confident, and true to where you are in life.
Great style isn’t built through nonstop shopping. It’s built in the editing and curating. Having a larger wardrobe doesn’t give you better style. In fact, I’ve found the opposite to be true, so I needed to cut back on the noise so I could hear my own voice again.
Have you felt this way? I’d love to hear your thoughts in the comment section.
Splurge or Save
So many of you ladies love the splurge or save outfits, so I have another one for you today.
This one has straight-leg jeans, a white linen shirt, a black & white bandana, red cat eye sunglasses, black earrings, red ballet flats, and a leopard print crescent bag. Can you spot the expensive one from the budget-friendly option?
In case you haven’t heard, Talbots is kicking off the summer with a Cyber Monday sale, online only…save 40% off your entire order. It’s for today only, so if you need something to round out your wardrobe, this would be a good time to look.
Here are my favs:
Thanks for reading, ladies, and be sure to wear what makes you feel confident. Please join the conversation in the comments, and let’s chat about the self-care aspect of dressing with intention.
Adore your blog! So refreshing to see a woman that thinks the way I do about her appearance!I have just discovered it and totally agree-I feel better if I spiff up a little. It is a matter of self respect, respect for my husband and I’ll confess, a little vanity too. Have you ever noticed that when you look your worst is when you see EVERYONE you know?? I don’t always wear makeup if I’m just running into town BUT I do make sure my hair is neat. I will use a good skin product too. I also put on a lipstick or a gloss. My rule: looking natural doesn’t mean unkempt or sloppy or horrors ugly! I have always coordinated my clothing so that comes naturally to me. It is not hard to be your best self without dressing up. During covid I completely stopped wearing makeup and yeah it was liberating, but Covid is pretty much over and I have started back wearing more makeup and have discovered Laura Geller cosmetics. Love them!
Now I do have email from some of my favorite shops, in particular Chicos. I watch for sales. Same with shoes. The urge to “click” is so hard to break!
You’re so right! It never fails if I look awful or don’t bother with my appearance, I do see more people I know. Often someone who I know is not particularly nice.
I am totally on board with this. One’s mental health improves when you make an effort to just be neat and clean (sadly showering becomes an effort for some as we age). I had a more extreme experience decades ago when we were invited to a Friday night cocktail party in June. We lived in what was a tony suburb of Manhattan. I came home after a long day and commute. It was hot and muggy so I showered, slicked back my wet hair in a pony tail and slipped on a casual dress. Don’t remember what my husband wore, but he probably was in his suit and tie from the office. I arrived to find all the women dressed to the nines in formal cocktail garb, jewelry and heels. It was in the late 80’s so things were a bit over the top, but I assumed an event in someone’s home would not have been that formal. I wanted the floor to open and swallow me up. After that event, I vowed to always be overdressed or ask the hostess (although I’m not sure she would have prepared me for the dress code anyway).
I feel your pain, just from reading about your experience. I would have been miserable. I’ve had similar experiences, although not as extreme and it’s not fun. How would you have ever anticipated that level of formality? I think the hostess should have clued you in before the event.
Thank you for today’s topic! It truly resonated with me. I agree that many people are putting less effort into their day to day appearance. I love a look that says “I put a little thought into this “ and putting on my face makes me feel happy. Great blog today!!!
I’m on a couple of cruise Facebook groups (Viking River, is that ok to say here?) and people are always asking what to wear and if they should change clothes for dinner. The majority of answers is wear whatever you want, no one notices or cares what you are wearing. I totally disagree, just because YOU aren’t paying attention doesn’t mean others aren’t. I DO and if I see someone dressed nicely I often compliment them. I enjoy getting a little “cleaned up” for dinner instead of the clothes I have been wearing and walking around in all day. But people today seem to want to just be totally casual.
I totally disagree too. I’ve been on a Viking riverboat cruise and always dressed nicely. I did notice people who didn’t so they can try to kid themselves, but people with discerning taste, DO notice others who look underdressed. That said, not everyobe cares and that is personal choice. I am happier when I make an effort to look nice.
My mother insisted on getting her lipstick on before I took her to the ER where she was admitted to the hospital with almost fatal pneumonia! I, too, put “my face on” even if I am not leaving the house and I think it makes me feel better. I have three girls who very seldom use makeup and it is sometimes painful to me when I see how they are dressed to go to the grocery store. I tell myself that it is because they are very confident in themselves, or are they just lazy? Who knows. I bet you make your bed every morning, too. 😄
You’re right. I do make my bed every morning. Always have.
I’m often appalled at the way people dress these days. I always dress nicely and wear makeup and jewelry. Sometimes people compliment my outfit, other times they’ll say something like “oh, I didn’t know we were supposed to dress up for this!”
Hi I really like this combination of red and black not overdone and zooshed up with the leopard bag!
Your post today really hit home, Jennifer, and our church’s youth garage sale will be the better for it. Reading of your digital detox was just what I needed to do to start my week! I love knowing what is going on in fashion but many times make compulsive and unneeded purchases. I just needed a little push to get me going. Thank you so much for your help today.
I’m so glad it was helpful, have a great week.
I was just talking to a woman about how taking care in what I wear makes me feel better. So true. If I just throw something on, I feel sloppy and unpleasant.
The photo of the save or splurge was hard today but the linen blend shirt versus the all linen shirt gave it away for me. The save is on the right. I learned to Jon when my mother put me on a stool and had me iron hankies and pillowcases. I used to love to iron but it has become painful with very arthritic hands so no iron shirts are a blessing especially from Chicos. My mom was always put together. She sewed most of my clothes and hers. I’m petite and got it from her. She had cute shorts and tops for yard work and gardening! She wore size 5 shoes and always got them on sale. I’m small too but wear a size 6.5 in summer and a 7W in winter to accommodate warm socks. Like you Jennifer, I sewed most of my clothes as petite didn’t exist when I was growing up in the 1950s. I’m 80 now and try to be put together everyday even when I don’t feel good. It cheers me up when I pass by a mirror and I smile. I copy your style a lot because of our similarities in coloring and size. I’m shorter at 5’1” so even petite pants usually have to be shortened. Regular size crops usually are normal length on me. I love to follow you and Pamela Lutrell because you are very real and down to earth. You feel like a friend and all of the readers are so interesting to read as well. I learned a lot from them as well.
I love this community of wonderful women too! I’m glad you’re part of it.
I am also on team ironing. I love this post, too, Jennifer. Yesterday at Church, there was a lovely and stylish older lady who was wearing a corsage given in honor of Mother’s Day. I so remember this being a very common practice back in the 60’s. One of my challenges in terms of looking put together is that I tend to really wear out the gym outfits. Therefore, going from the gym to anywhere else means I am going in old worn stuff. I know there are some people who change at the gym, but that is not me. I guess I need to update some of the gym stuff. Lately I have been thinking about the absolute best outfits in my closet. Those that score a 10 out of 10. There are not necessarily formal, but just really good colors, fabrics, lines and styles for me. It is an interesting thought process. Even jeans and a nice t-shirt can be a 10.
This post also resonated with me. My mother, even if she was in jeans and a sweatshirt, would tie a pretty scarf around her neck and bring the whole outfit together. When she traveled back to England she always dressed up for the plane ride, so that she looked her best when she deplaned and was met by friends. My grandmother, her mother-in-law, at 90+, would sit in her chair watching TV or listening to sports radio, dressed casually (she lived on a ranch) but always with clip-on earrings and lipstick just in case someone dropped by. I miss them both.
They sound lovely! Such great examples
What a wonderful, thoughtful post. Really resonated with me. I quit following soooo many blogs because, whether intended or not, I felt pressure to buy. And I lost my style mojo. Was I wearing something because I loved it and it felt like me or was I just copying someone on social media? When I realized it was the later, I unsubscribed, unfollowed, etc.
I never feel that pressure with your posts. you’re thoughtful, funny and provide helpful insight on a variety of topics. I think all of that is reflected in this community and their responses.
Love you, Jennifer!
Btw…in that first pix? Your hair looks great
You’re so sweet Linda, thanks. My hairdresser retired and I am in desperate need of a trim, so it’s longer than usual. I was losing my style mojo too so when I looked in my closet I saw too many things that didn’t look like me.
Thank you for encouraging a return to more thoughtful and polished ways to present ourselves, not only to others but as you said, to ourselves and the way it makes us feel. Self care, not selfish care, is so important. I feel in so many ways society puts more emphasis on hair and face only.
Even if I’m only seeing myself I wear my faux pearl studs every morning and my face immediately looks brighter. A little concealer, sheer lips, blush and brows makes a huge difference in how I look and feel.
You can wear comfortable clothes and still look polished and elegant, as you showed!
Thanks for a great and timely post!
Hi Jennifer happy Monday! Love your messaging thank you. I have moved away from other bloggers because of the over sell. I just can’t afford fashionable items over a certain amount and sometimes the outfits are just crazy. I know it would cause distress to me and my husband if l did so l appreciate your sound wisdom. I always put on make up and dress well when l go out it makes me feel more in the moment. Happy week friend !
Have a great week!
Jennifer, my favorite post are the ones where you show us how to style something or put together different looks from things we already have in our closet! I recently “discovered” that I could create same color outfits that had that matching two piece look with items I already had in my closet without buy new ones!