"Do you feel your body looks as good in the clothes you wear now as it did in the pencil skirts & jackets?"
An interesting question,Caro, that I had to think about for a while to see if I could put my thoughts in some kind of order. So here goes:
In my case, I think that my structured clothes looked good on me because my body shape has always looked its best in a tailored fit. Pencil skirts, tailored blazers, button-down shirts, slim trousers, and heeled pumps gave me a polished, professional look that was my preferred work image. This style, however, started to make me feel overly up tight and dated as I grew older. For me, the challenge was to figure out how to translate this look to more contemporary, less severe version that would feel comfortable but still be polished and flattering.
I need clothes with a definite shape to flatter my figure; the volume in ethnic-inspired wear or Eileen Fisher-type pieces has never looked good on me. Boxy cuts, layers, and drapey fabrics make me look shapeless. My solution was to look for variations of my structured clothes that would give me the same effect as those classics, but be more comfortable and easier to wear. Instead of pencil skirts, I switched to a straight-cut, pull-on type of skirt that gave me the slimness of a pencil but with more ease and comfort. My jackets still have shape and structure, but are now made of a knit or stretch fabric so they are as comfortable as a sweater. My pants have a non-binding waist to avoid a muffin top look under a slim-cut, knit or woven, top. I look for clothing that is body conscious, but not tight or revealing. I also like items that are a bit distinctive in cut, color, shape, or texture so I don't have to fuss with accessories to make an outfit look good. I also prefer quality garments that have better construction and a more flattering drape on a mature body shape; buying a few good pieces makes more sense to me than having a big wardrobe of things I don't really wear.
All in all, most days I like my current wardrobe; it works for me in a way that those pencil skirts and structured blazers didn't anymore. And, yes, I do think that I look just as good (dare I say, maybe better) in my clothes these days.