First off, I should explain that few old houses in New England actually have much by way of closets. So I’m actually talking today more about personal wardrobe and style.
One of my long-term planning notes was this, for my shift into retirement:
Focused look: new jeans (black/green/gray); sandals (fewer socks; also, they travel better); blazers for the pockets.
What actually emerged was quite different.
I shifted from denim jeans to tan cargo pants, for their pockets, especially.
Instead of my customary oxford shirts, I wore turtlenecks in winter, and Aloha shirts in summer. (I still largely avoid T-shirts.)
Instead of that blazer, I rely on a messenger bag to hold my reading glasses, cell phone, emergency cardiac prescription, choral music scores, and so on.
My style, such as it is, has emerged from yard sales, mostly. These days my focus is on wearing them till they give out while also downsizing. You’d be surprised how many compliments I get.
Jnana's Red Barn 