I've been retired just one year ago December 1, and a few weeks ago spent a couple of days doing a big closet clean out. Mostly what I culled were warm weather work clothes. I pulled out what I didn't wear for church or social activities during the spring and summer to be donated. I kept the dressy things I had worn to church and a few parties/events. I had done the same process on my cold weather items last spring.
RunCarla has asked me several months ago whether I would continue wearing my skirts in warm weather as I had for work. At the time I thought I might, but I did not, choosing colored sheeting or chino shorts instead. Skirts were worn to church and only a few other times. Skirts were a large portion of my donation pile this time, as were many dressy sleeveless blouses and summer toppers and jackets. Any things that I transitioned to retired casual, I kept.
I run or work out in a gym or a class several days a week, so I have a small dresser full of athletic wear. At home I mostly wear the same things as out, but occasionally tend to go with cozier layers in coldest winter, such as yoga pants, wooly socks, and some old long sleeve cotton shirts and gray sweatshirts I got from races. My activities at home are reading, sewing and quilting, making mixed media collages and greeting cards, cooking. Currently my outside activities are church, exercise and running, one monthly book group, going to galleries (alone), college basketball games with husband, and spending time with daughters and families. One daughter lives an hour away, and the other an overnight train ride away. When I finished my last volunteer job (after 40 years of various volunteer positions in lots of organizations) a year before I finished work, I intended to find something else to volunteer for, but have not. I was asked to chair something at church, and just wasn't interested in being in charge of anything right now. The last couple years of work really burned me out, I think.
Now that it's cold weather again, here are examples of what I've worn in the past several days for my retired life:
1. Activities: haircut, trip to daughter's for dinner and to deliver a bed my husband made for oldest granddaughter. Charcoal skinnies, black and white striped button up shirt, black with yellow stripes pullover sweater, dark gray and black striped socks, dark green Converse tennies.
2. Activity: family Thanksgiving at in-laws (very warm house). Dark green skinnies, green/cream mini-stripe long sleeve tshirt, black/white geometric print quilted vest, cream socks, green Converse.
3. Activity: family Thanksgiving (lasagna version) at my home with my daughters' families, including kids age 2-8. Denim skinnies, cream/gray striped long sleeve tshirt, citron boyfriend cardigan, turquoise Converse.
4. Activity: shopping, errands. Denim skinnies, pink/white stripe long sleeve tshirt, navy quilted vest, colorful pink/white/navy/blue/yellow bird print socks, pink Converse. It was very warm that day so I didn't need a coat.
5. Activity: book discussion group at senior rec center, shopping. Dark denim skinny jeans, white blouse with tiny blue print, navy pullover wool sweater with bell sleeves that have wide cream, gold and burgundy stripes at the bottom, gray socks with navy spots, dark green Converse.
6. Activity: staying home sewing and quilting (on long arm), cooking dinner, laundry, changing sheets, working on collages and greeting cards. Corduroy gray jeans, purple long sleeve tshirt, gray fleece vest or black pullover sweater, gray socks, gray Adidas tennies. Or some variation of corduroy jeans, long sleeve tshirt, fleece vest or pullover. My main rules are to stick to two colors plus one accent if unavoidable, MUST wear socks that coordinate, MUST wear makeup and earrings, try to look like I cared. HA.
7. Favorite from last spring, activity of art class, errands. Gray tshirt with butterfly design in rust, peach, teal and gold tones, citron cardigan, washed old wide-ish leg jeans, gold socks, turquoise Converse.
So you can see that my wardrobe is not dressy. I rarely wear any jewelry other than earrings, watch and wedding rings, whereas I wore and enjoyed bracelets and necklaces everyday while working. I feel best when I have on a little quirkiness, but not so much as to look nutso.
Good luck figuring out what is YOU, in what you do, how you spend your time and what you wear.