I have reached some Twilight Zone tipping point. My every day look is becoming a mix of feminine and "I don't care". The jeans I wear most every day are Lee petite Classic fit, and I love graphic tee shirts like the Levi one above. Shoes, Skechers Sport Women's Premium Sneaker.
For all of the above I am showing an Amazon link but these are available most everywhere. The Levi outlet stores are great for the tee shirts and I have this split neck tee in several colors. The Skechers and Lee jeans are always available, to try on, at JCPenney. The Sketchers above come in wide.
I do not seem to be getting a lot of checking me out looks, as in "what is wrong with this picture". However I am getting a good share of "what can I get you Ma'am?" at restaurants. Maybe it is the hair. The back is tapered, in a very feminine cut (on purpose) and the top and sides are full. Because of my age, I very much live in the "invisible" zone so blending in is OK.
Your challenge - Wear something that is just a little outside your comfort zone. Next step - add to it. Your confidence soars as does your fun. Being authentic does not always involve a dress and heels. Next time at the mall, people watch and see what everyone else is wearing. Blending in is easy. Plan your escape from the mundane.
So when they ask "What can I get you Ma'am?" - just smile and order.