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.
Amen to the ironing. I find it relaxing too. My mother ironed the pillowcases and I must say I do too ! It’s wrinkled after the first night but I love the crisp pretty pillowcase after changing the sheets. Good post this morning
I too really enjoy ironing, I also find it relaxing.
Having grown up in Montreal, Canada and lived in Europe for 5 years, I still like to look put together although I currently live in Alberta (very casual, sometimes downright frumpy). It really does not require that much effort, you need to get dressed why not choose wisely.
This was a great post! From the first pic in which you had the brooch on your white shirt, I thought “how cool is that?”. I recently unsubscribed to several blogs with similar topics as yours. Because I seldom “clicked” on the finds. As for being over/underdressed, for 20 years I had a high ranking corporate life and in that era, at a conservative (financial) industry, that meant no pants, only skirt suits/dresses and heels with pantyhose! When I left that life my first act of rebellion was never to have to wear pantyhose again: either wear tights in colder weather or go without. I look back and see that covid led me to dress too casually. Will spend this summer on-and-off purging my wardrobe. And I am migrating to a new look, in terms of cuts/colors. Primary candidates for purge/donate: sleeveless items, scoop necks, and brightest colors. I will, of course, keep some that are favorites for other reasons, but at least I have a plan. What I really hate about the “underdressed” issue is going out to a restaurant in which dinner for two, with wine, will run $200 or more, the service, decor and ambience are great, and seeing folks in sweatpants, ripped jeans, well-worn athletic shoes, sometimes even ball caps.
That will be a fun exercise. Totally agree about what we see in restaurants…nice restaurants!
Jennifer,
Enjoy your posts greatly! I totally agree in the self-care aspect. Plus, I love and need color in my life daily. Today it is a soothing lavender!
By the way, I have the gauze J Jill button down beach over-up and love it. (I think you had an earlier post on it)
Color is sort of magical
You look great in your outfit to the grocery store. I was recently inspired by your posts on broaches so I found my mother-in-laws parrot broaches and wore it to my daughter’s baby shower. I received many compliments! Putting it on made me feel more confident for some reason. My mother always looked put together. Her hair was always styled and she never left the house without her lipstick. Shoes and bags had to coordinate. I think this has also influenced me.
Amazing!
My mother always dressed to be presentable. She tended to overdress. I remember her making me change clothes before leaving the house into something “presentable”. Im 70 yrs. Old. it stuck with me.my entire life and has always served me well. Thank you, Mother!!!
Yes! My mom talked about needing to look presentable too 🙂
Thoroughly enjoyed your post today Jennifer! My grandmother, not my mother, was the one who taught me to start the day out right by putting my face on, etc.
She also taught me to be sure to take off all makeup before going to bed at night and she had beautiful skin! I love looking put together even when dressed casually. I’ve passed this on to my daughters, granddaughters and now to my 16 year old great granddaughter! Yes, i’m an oldie (85).
Am in the Northwest so getting ready to wash and put away all my cashmere
and wool sweaters. Do you wash all yours or take some to the cleaners?
Thanks for all of your ideas!
That is amazing Sandy, Bravo! I wash all my cashmere sweaters either in the sink or in my washer- on cold and delicate cycle. Then I drape them over my drying rack to dry. Finally, I iron lightly and defuzz or use my sweater shaver before I put them away for the summer. They never look, smell, or seem clean after they come back from the dry cleaners.
Thanks! That is my preference but was wondering what you did. You probably told us in previous blogs but I couldn’t remember. Lol
Great insights! A client once told me that “everything you own takes a piece of your energy”. I have always remembered that and think of it often when cleaning out.
That’s brilliant!
My mother also ‘put on her face’ and took great care of her skin, and it showed. I try to follow her example. Every morning after my coffee I say to myself, ‘time to face the day’ and go upstairs to make myself presentable. It’s nice to have a ritual to start the day, and taking the time to do so mindfully means my days start off on a positive note. Thanks for these reflections about why it’s important.
Ditto for my mom. She always used Noxema and had the prettiest complexion.
OMG, your post was particularly relevant today! My husband and I are going to lunch at the home of a dear friend who is in her mid-80’s (we are 70’s). Whether our lunches are at her home or ours, she always looks well “put-together” and stylish. (I want to “be her” in 10 years!) My husband was wondering what to wear today and mentioned that he might wear a long-sleeved T-shirt, as the weather is cool and damp. I told him I thought that wasn’t a good choice, as she always makes the effort to look nice anytime we see her and we should do the same. He reluctantly agreed. Then, I opened my email from you and couldn’t believe we had just had this conversation! I read most of the post to him!
THANK YOU for this wonderful reminder that we owe it to ourselves to look our best, which helps us feel our best!
P.S. I LOVE to iron! It’s instant gratification and very calming. Plus, no wrinkles!
You “hit it out of the park” today, Jennifer!
I’m so glad you liked it, Anne. I bet she loves to see her guests dress nicely too! I have a neighbor like that and always looks so lovely. I want to be her in 15 years. It occurs to me that I should tell her how inspiring she is.
I absolutely got my sense of style from my mom and older sister. My mom would have the rollers in her hair every morning and I did too. She sewed a lot of our clothes. I always take time to get put together and put my face on even if just going to the gym or the store. My husband knows to allow time for me to get ready to go out. I think it’s even more important as we get older to not feel invisible. I love it when my friends say how I always look put together. I am having difficulties lately finding petite clothing that I like. For the first time I feel out of style. A work in progress I guess. Thanks for listening 🌼
Being petite does pose a challenge because so few brands are caring our sizes. I’ll be on the lookout for us.
I agree and live life Styled as I Leave the House. Just a little effort goes a long way when putting together an outfit for the day.
I have been feeling the same way as you just blogged. We have so much coming at us all the time to consume that it becomes overwhelming. I started looking at the waste in my consumption and what I could be doing to control it. I have decided to not even be tempted to look through the adds unless there was a really good deal going on and I needed something. “Need” is the word I am going to be addressing
Yes! I need very little.
Thank you for this post. I too follow too many influencer sites. And yes they are not my style, yet I still order something I don’t need. I am going to cut it back now. It is so easy to get overwhelmed. Thank you for posting about this. I love your statement about “showing up” it is so true at my age how much more important it is than when I was younger. I appreciate you and will keep following your style. It is genuine, classic and works for me. Jennifer in Port Angeles, WA.
I love your town! We’ve driven though many times on our way to Vancouver Island.
My mother was my inspiration to dress the best we could for what we would be doing. I am thrilled to see our daughters doing the same.
The times i have left the house looking worse for wear I see someone I know (like my my mom warned). I have started just deleting or unsubscribing from things that scream you need to buy. My budget at this time isn’t allowing it…lol. It is why I enjoy your blog. I can see something I like and maybe can put the look together. I do love your shoe choices, sometimes out of my range, but i love that you stress comfort!
I do splurge on shoes when necessary because they can make or break an outfit, and your day!
Good morning! I too learned from my Mom who was always dressed nicely and as your Mom said, “had her face on”. I saw her that way into her 90s and I try to look good every day and it does feel good. Thanks for your inspiration and sharing. Have a great week!
I could not agree more with everything you said! Dressing is self care, and it shows self-respect as well as honoring those around you. Nice looking clothing can be obtained on any budget. Attention to grooming is essential. A nice appearance with hair combed and light makeup can be achieved in 3 minutes or less. Thanks, Jennifer, for a great message.
Even if I don’t expect to leave the house, I “get dressed”. I have nice things and I wear them. Even if it is 3pm before I shed the yardwork clothes, even if I just put on jeans and a t-shirt, it’s a shirt with come details and nice accessories. It’s just discouraging to walk past a mirror and not see the person who lives in my head. People sometimes will make a comment “you always dress up” and yes I do. Totally worth it!
I hope you don’t mind if I steal your comment, “it’s discouraging to walk past the mirror and not see the person who lives in my head”! That explains it so eloquently!
You always look amazing and I very much like the idea of wearing a brooch the way you did in this photo. Clever and eye catching. I do need to weed out my closet as some clothes I like several years ago do not reflect how I now dress. Going out to lunch or dinner with girlfriends allows me to use jewelry I do not get to use very often. Like you I rather be a bit over styled than super casual.
Yes!! Meeting girlfriends is so fun.