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Your clothes sound perfectly fine to me - and not that dissimilar to how I dress in my 50s. Not to say that I think you do or should look like you are in your 50s, just that I think what you are wearing are grown up clothes, and fine for adults of all ages.
One potential concession to your grandmother you might consider would be to add something like a scarf - those are age appropriate for you but might add that little touch that Grandma would love?
Frankly you sound like a lot of 30 somethings in New England I know. They do occasionally dress up and like summer type dresses and flats but very few wear heels thank god. For dinners and the like in the winter you might choose a nice sweater instead of a long sleeved shirt. Scarfs are also the thing it seems though not all can pull them off. You might choose fancier flip flops and a nice ankle boot for when you go out to dinner.
Wear what you feel comfortable in. What you described sounds like it would be fine most of the time. I see plenty of women much younger than you in all sorts of dresses and skirts. Some frilly, some not. You sound a bit in a rut as far as variety and experimenting with different styles, but if that's the biggest issue between you and your grandma..... you should both consider yourself lucky. Hey - for her birthday maybe you could find an old prom dress to wear. ;-)
Your clothes sound perfectly fine to me - and not that dissimilar to how I dress in my 50s. Not to say that I think you do or should look like you are in your 50s, just that I think what you are wearing are grown up clothes, and fine for adults of all ages.
One potential concession to your grandmother you might consider would be to add something like a scarf - those are age appropriate for you but might add that little touch that Grandma would love?
You are right... It's a look I see all ages wearing from grade schoolers to 80+. Take off the UGGs and replace with athletic shoes and it sounds about what my late Mother usually wore and she was well into her 90s.
I think what you wear now is fine. 30-year-olds today dress and look much different than they did in 60s or 70s. When I watch old shows and movies, I always think of how old people used to look back then.. a lot of 30 something year olds back then could pass for their 50s! It must have had at least something to do with their clothes and hairstyles.
First, instead of imagining what your grandmother thinks, why don't you ask her?
Personally, I think that at 30, you should be able to dress as an adult. Not in your leisure time, but at work, at least. Not jeans, not tanks. You're getting a little too old for "cute." It's possibly that although your grandmother's taste may be feminine, maybe all she wants is for you to look like an adult.
That doesn't mean looking matronly. But, yes, a little more tailored, a little better quality, a little more formal.
My late grandmother was born in 1917, and in HER day, women "of a certain age" (literally meaning over 18) weren't supposed to wear their hair down - or WILD, as she would say. My sister and I have crazy naturally curly hair, too, which we both were keeping long by high school. Every single time we saw her, grandma would nag us about putting our hair up in a "nice, neat bun." Oh, and "what's wrong with a bit of lipstick??" Eventually we just gave up arguing, and would do the bun and lipstick on the way to her home. She lived across the country for most of our lives, so thankfully it wasn't a regular thing.
Anyway, my point is that different generations have their own standards for dress. Sometimes it's not worth arguing with them, especially if it's someone you don't see regularly... but hair and lipstick is easier than full-on clothing, so I guess you'll just have to ignore her? Dunno, sorry.
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