Hi! I'm 51 and I'm also struggling to find the right style for my age. I never ever think of myself as "old," but I have to stay away from frills and puffs and anything too cutesy. I'm aiming for classic, but not boring. I tried to wear zip up hoodies but they felt way too young for me. I don't know why. The hood maybe? I like a casual look, but I just couldn't get that hoodie thing right. I love the look that Angie recently posted - the jeans tucked into riding boot look. I think that might work for our age. Maybe with a simple top and a simple boot. Honestly, I don't know if I could rock a pair of Doc Martin's anymore. I'd just feel like I was trying too hard. But I guess it's all in the attitude. If you can carry it off, go for it!
Since I was laid off from my office job several months ago, I've been reintroduced to wearing jeans every day, and it really is a challenge. In general, with my everyday jeans, I like a knit top that is a few notches above a t-shirt. If it has a lot of pattern, I try to make sure the cut is simple. If the cut is simple, I try to find a great color. I also love a patterned top under a jacket. You get just a little pop of color, without it being overwhelming.
It's harder in the summer to find tops. I don't like to go sleeveless because of the wiggly upper arm thing. And I avoid any top that has that "pregnancy" look going on. That feels really young and silly on me now.
I don't wear front button shirts at all, mostly because I have a large bust and they rarely fit right. They ride up and pull and I don't feel comfortable. But if they work for you I think that can be a great look for our age - nice jeans and a crisp buttoned shirt. Maybe even wear the shirt unbuttoned slightly with a simple cami underneath. Simple and elegant. Wish I could wear it but it just doesn't look good on me. Knits are better for me.
My all time favorite look is dark jeans, sleek boots, a simple top and a killer blazer. Only problem is I live in LA where it's usually quite warm, so a blazer isn't practical most days. I'm still looking for a warm weather alternative.
Sorry if this isn't much help. I'm still learning and experimenting myself. I have found though, at this age, that I do look better in simple clothes. The challenge is to find simple clothes that don't look boring. And they have to FIT well.
Oh - also - I do NOT have a lot of money to spend on clothes! So many articles I read assume that if you're 50 you're automatically a CEO and can drop a couple of thousand at Bloomies. I can't! I shop Ann Taylor and Macy's and Nordstrom's on sale!
I look forward to more ideas from other fashionable 50's!