I'm 66 years old, retired, overweight, bald and have very large breasts.
In the summer I like to wear khaki shorts (not too long, above the knee), a polo shirt and tennis shoes. I wear Nike Pegasus shoes, which is a woman's shoe, but there is not much feminine about them. I keep my fingernails long and well maintained. My legs are strong and shapely and without hair.
I think the most incongruous thing about my appearance is the combination of obvious breasts and (mostly) bald head. When I wear my Panama hat, I get gendered female.
I hang out with older classy ladies, like the League of Women Voters and blend in well with them. Most see me as a man, but a man of a "special" variety. I also do water aerobics at the "Y". The class is typically 20 women and 2 or 3 men. The same thing pertains there. After a while the women don't see me as much "different" than them.
I haven't owned pair of jeans in a quarter century.
Polo shirts are very versatile. A larger size hides my breasts (somewhat) and a tighter one is very revealing. Men pretend they don't see them. Women, look and smile at me. I smile back.
Randi