So it’s 4 1/2 years since I left the workforce, and since I got nothing but time, I’ve decided to get rid of work clothes hanging there getting dusty. Mostly dress slacks, some jackets, shoes, skirts and blouses etc. But something in me keeps saying " YOU MIGHT NEED THEM SOMEDAY!" Plus I spent some serious $$ on them, although, I’m sure I got my money’s worth out of them.
So tell me, how did you ruthlessly get rid of the office wear?
I didn’t have fancy office wear. Closest is Dockers khakis which I only wear when I go out somewhere reasonably nice. My shorts I’m happy to wear in retirement.
As for your stuff, why not find a nearby thrift store supporting your favorite charity and donate them whenever they reopen. Save a few of your favorite just in case.
I have a gorgeous collection of ties that I’ll never wear again, but I cannot part with them. Perhaps I’ll convert some to face masks.
I was lucky.
Over time, my career path put me further and further into the field, labs, test ranges, etc. Since I saw bosses (literally) 2 or 3 times a year, nice clothes became unnecessary and by the end I dressed exactly as at home. My wardrobe didn’t change at all on weekends.
One of the most disturbing effects of the pandemic is realizing I might need to buy a suit. 
Down-define them to become your “weekend grubbies” and wear those nice slacks, etc., for doing housework, cleaning, gardening, and such.
Retired now 7 years. I was actually thinking about this very thing yesterday! My plan is to toss everything I used to wear to work except for: 1 pair slacks, 1 sport coat, 1 fancy belt, 2 dress shirts, and ONE TIE. That is literally all I need. I would only dress up for a wedding, or a funeral. Other than that, casual 24/7/365.
See if a local agency takes donations of nice clothes for a job interview wardrobe for people who can’t afford it. Dome colleges have a “professional closet” as well.
Neither of the jobs I retired from had hard-core dress codes, although the first one adopted a strict no-jeans policy in the last year. Oddly enough, I still wore black jeans and nobody said anything… but I digress.
The only things I culled from my closet were some cotton cardigans that I gave to my daughter - I think she took 3 or 4 of them, and I have one that she didn’t want. I continue to wear everything else - the jeans and khakis, and the various tops which were mostly nice t-shirts and henleys. I have a couple of nice, dark pantsuits and one dress - I figure then next time I’ll need one of them will be for my mom’s funeral.
I’m a work clothes clothes horse. The dress code is business casual and I always dress smartly. I calculated that I have 104 weeks til retirement. I work at home 2 days a week, so 345 days in the office. I wear jeans one day, so about 200 dress smartly days. I recently culled my closet and realized I have no need to buy any work clothes. I have thought about retirement and plan to keep a black skirt and blouse , a black tweed dress (both can be worn for funerals/dressy occasions) and a 3 seasons wrap dress. And a pair of navy blue dress pants. I have no remorse about getting rid of things that no longer serve me.
I give unwanted clothes to Amvets or Purple Heart.
Like others have recommended, most of my clothes went to various charities in the area. I kept a couple of jackets, 3-4 nice shirts, and 3 pairs of slacks, everything else in the closet is t-shirts, jeans, and polo shirts. Like peedin above, it didn’t hurt at all to let them go.
If it has to be ironed, get rid of it.
If it has to be dry cleaned, get rid of it.
If it doesn’t go with sneakers, get rid of it.
I’ve dedicated my entire retired life wardrobe to t-shirts that say fun things, like, “Sometimes Life Sucks The Jelly Out Of Your Donut.”
Or, “I Thought Getting Old Would Take Longer.”
I wear them with comfortable pants and sneakers.
~VOW
Yes you can! One thing I’ve learned over the last months is that “Oh, I could never get rid of…” is the worst attitude to have when you’ve got time and are trying to simplify your life.
Yes! Good for you. You are my spirit animal for the rest of the day.
Over the years, I dressed more and more casually at work and no one said anything, so I have very little that I’d only wear to work . I just have to toss the dockers and dress shirts that I “might wear someday, to… ummm, somewhere… in case we go to that fancy small plates restaurant downtown…”
[spoiler: we will never go to that fancy small plates restaurant downtown]
Never going to wear a suit again?
OP, slightly formal wear is back these days amongst the younger crowd. So, maybe you might get some good coin.
On the other hand good work clothes are expensive and quite a cost for young workers. So maybe offer some of them to a child or a relative or a friend child/relenting.
When I started, my now deceased Great Uncle let me raid his cupboard. I got some fine dress shirts, blazers and a coupe of suits out of it and since it had been so long they were back in fashion.
Trust me they will thank you.
No - if it has to be dry cleaned, don’t buy it in the first place! 
I still wear my professorial jeans and flannel shirts all the time. No need to discard anything. I still own a few ties and one suit that I had to get for my daughter’s wedding (my wife insisted).
Donated all but (I think) two ties to Goodwill. Some nice silk in there.
Donated all but one or two dress shirts.
Donated a suit and a tux.
Kept a couple of sport coats and some khaki pants. I think the coats date back about 30 years, but are still serviceable.
Since most of my working life has either been in uniform or in non-suit environments, that’s about it. When I left the military, I got rid of all my utility uniforms and gave my dress blues to my grandson, since he asked for them.
I decided last October to retire in January. I went through all my summer work clothes and gave about half of them to a thrift store. After I retired, I gave about half my winter work clothes to an organization that gives outfits to low income women entering the workforce to wear for interviews. I kept the rest thinking it would be fun to sort of dress up for lunches with friends or for dinner parties, and didn’t want to just live in jeans and t-shirts. Now I’m wondering when I’ll ever get the chance to wear them again.
I hung on to my best dark suit for as long as I can still get into it: I need it for funerals.
I just got a whole new professional wardrobe, due to having lost some weight and my previous “wardrobe” being really just rubbish (the clothes were fine, they just weren’t fine for my body). I ended up selling all my old stuff on eBay and so far have made $500, with some items left to go.
Some things to remember:
- Stuff goes out of style, and somehow that style goes fast. Everything is already 4+ years old. Even if what you have is considered “classic” there still might be subtle changes in cut, color, fabric, etc that make you look worse in your clothes as they get older.
- Your body will change and your clothes probably don’t fit the same/correctly anymore.
- You need room in your closet. Everyone needs room in their closet.
- If you do in fact NEED one of these pieces in the future, it won’t be an overnight emergency. You will have time to find and purchase it with haste. And it will look and fit better.
- Someone out there is going to be absolutely tickled to find your item in their charity shop, and put it to use in a real working environment.
- Sell that shit! Money rules!
ETA: Do keep a “funeral outfit.” Those sometimes come fast.
I don’t go to funerals or weddings, and if I’m ever trapped into going, I’ll rent. And I’ve always hated ties, so will never wear another one. Such a stupid accessory. The most formal thing I do is a jacket and a pullover.