Age has freed me up to dress to please myself and not care at all whether I blend in as long as I dress respectfully for the situation. That may end up being somewhat overdressed compared to others whom I may consider underdressed. . .

Especially since I mostly work from home, I am a fan of juxtaposition, BUT I have learned that there are a few things that will make me feel too business formal regardless of what else I wear with them: Dry clean only anything, especially blazers and pencil skirts and heels which my feet hate regardless. Umm, but those juxtaposed outfits are mostly in my head and not what I wear.

Somehow, it is stuck in my mind that colored and print jeans are dressier and more polished than blue jeans so I don't wear actual blue jeans that often. I also don't wear gear except for exercise. Except for my very obviously gear shoes, I haven't found or liked the look of sneakers that make my feet happy. I have a pair of wool Allbirds sneakers on the way to me (unable to get the Finds to work), because to my eye they look more fashionable than the norm.

Toppers/third pieces can elevate a look if they're not fleece. I run cold so am almost always wearing a pleather moto vest, scarf, or both. And I wear belts, mostly to hold up my pants which would otherwise slither down, but also for fashion. My waist has thickened so I mostly semi-tuck.

This thread continues to be great. Jussie, you’re wondering about levels of trendiness... so I’ve been thinking about it... and I realize lately I’ve been going for really, really trendy pieces- like, crazy and out-there- to add to my wardrobe. I think it’s because something really trendy is obviously casual. A navy tee shirt could be worn with jeans or it could be worn with a suit, so it seems kind of blah and in-between (of course there’s a place for it in my closet anyway). But a bright yellow floral bomber jacket is obviously not business wear, so it reads casual, fun, stylish. It brings attention to the fact that you’re not just wearing your business basics on the weekend, but you have put time and thought into purchasing casual items, I guess.

Jussi, I hope this can give you some inspiration :
https://www.everydayhealth.com.....chic-look/

Great thread! Two other thoughts: 1) It might be helpful to sort out if you prefer a different style persona for casual vs. work. 2) If you haven't yet, evaluate if the types of activities you need outfits for are being satisfied with the clothing you have or if another piece or two are needed.

Smittie, Aquamarine, Janet, Anchie, Gigi, Suz, La Ped, Leslie, kkards, Lisbeth, Torontogirl, Joy, Sterling, Katerina,Jessikams, the Cat, Aida, Donna F, Angie: Thank you all for adding your brilliant thoughts. I can see this is a topic a lot of people have been thinking about. All the suggestions and questions you guys have raised are very pertinent.
Why do I feel overdressed? Because people in my area seem to either wear work clothes OR high-tech sportswear OR dressy clothes if they going out somewhere nice. There does not seem to be a lot of people wearing nice casual. This is more of a noticeable thing for me because I only work part time, so I have several days a week where I need something to wear. I am happy to wear sportswear a couple of days a week but any more than that and I start to feel like a real frump.
Summer casual is easier for me because I like a boho-lite beach look. So at least I know what i'm aiming for!
But winter is a different story. I have created a Pinterest page for inspiration. Matter of fact I might emulate something from that tomorrow!
I agree that shoes are a great help, and some of my casual shoes are very unstructured, so maybe that's something to look at changing.
Also I only have one warm casual coat and I am very bored of that.... so there's a wardrobe hole right there.
On a positive note I have quite a few beautiful woollen pullovers that I enjoy wearing.
Thanks again everyone. I need to do some more pondering and experimenting I think... this is a tough nut to crack....

Here's my Pinterest winter outfit idea page if anyone's interested https://www.pinterest.ca/jsmit.....fit-ideas/

I've been pondering this for a while, since I'm a SAHM during the week (I work weekend night shift in uniform).

I think fitted is key - either on top or on bottom if not both - I tend to go fitted on the bottom (jeans usually) with either a fitted tee/jumper or a looser top if it's hot. Make-up/jewellery/perfume/styled hair always makes it look like you've made an effort, even if you've just chucked on the nearest top/trousers! Trust me on this; even rushing out of the house 5 mins after I've got up because Child has to be at school, putting earrings/perfume/lipstick on can make it feel like I've been up long enough to be organised!
Sneakers can casual down jeans and a office-y style/dressier top, but do make sure they're clean/crisp/not too obviously trendy. Or boots/oxfords in winters or more on trend sandals/flats to smarten up jeans and a slouchier top.

Hope this helps!

Jussie I still see boho in those pinterest outfits so you won't be deviating too far Maybe take the "beach" half that pops up in summer and convert to "cabin" for winter.

I used to work for corporate America so the workroom sleek look has always been my thing. When I quit and went to work for myself I had the same problem...always overdressed. My go to look is a pair of great skinny jeans (I love Lola brand because they have built in slimming support and don;t look like mom jeans, even though I am a mom), a button up top or white look tank tied at the waist, a pair of low heels, and if it is winter, a blazer. Always ready for professionalism if you need it, otherwise you come off as being classic casual chic!