I've worn trousers most of my life. When I was four, my mother was trying to get me to wear a skirt, so put all my trousers in the wash, thinking that would get me in a skirt.
(I refused to go out until I got my trousers back)
I'm gradually increasing my observance(I view it as a spectrum, right across all the threads of Judaism) and the other day had a little lightbulb moment.
I bought a long denim skirt(eBay. With the exception of underwear and footwear, I buy clothes secondhand, charity shops - though with agoraphobia, that's not so easy. Hence....eBay!) and I really like wearing it.
And today, the phrase"accidental modesty" popped into my mind....that's how the skirt feels. I know I'll not be a skirt only wearer, but it was a pleasant and inspiring thought.....at 59, I grew up with mini skirts and was a very....flamboyant?....dresser. Too much to go into here and now, but these days I dress for no one but myself.
Finding my way, step by step. Like putting together a jigsaw of myself....still the same pieces, but on the other side: same puzzle, just a different view. It's proving to be surprisingly interesting along the way.