Hello, I'm new here and I am in desperate need of fashion advice/help. I'm 36 years old and I feel like I dress in clothes that a 50 year old would wear, but worse. When I was younger (teens-20s), my mom would always question everything I wore and I ended up dressing sort of tomboyish at times (even though I'm not a tomboy) and/or frumpy in bulky, oversized clothes with no shape or fit, usually in dark colors and somewhat masculine or androgynous (not the look I'm going for but the only look I've know). That's how she used to dress and I would hear about it until it was something she approved of even if I didn't like how it looked, didn't like how I felt in it or how it made me feel.
Now that I'm 36, I've spent the past 10 years trying to find a style and I feel like I'm a lost cause because I end up back in the same boxy sweatshirts and stupid jeans that don't fit right but I still keep wearing. I like the classic looks but not too old. I'm not really sure what's trendy but I'm not a fan of wearing workout pants outside of working out or hiking/riding and I don't like the distressed/worn look. Take today for example, it's chilly here (about 60F) so I'm wearing the stupid jeans that are cut so weird that they don't stay up even with a belt, a small sweatshirt that swims on me, tennis shoes, and my hair in a bun (think schoolmarm bun - it's a whole other issue that I have no idea how to content with). I work for a printing company and it can get dirty, I have to load things into customers cars and it gets HOT in the summer but I want to look presentable and put together, not like I just got off the treadmill or pulled something out of my mom's closet. I don't ever feel comfortable or feel good about myself in my clothes but I want to. I'm tired of the same old thing, but I don't know where to start or what styles are right for me without looking too young or too old.
Any help, advice, guidance ... anything is appreciated. TY