Steve Jobs black shirt, Mark Zuckerberg gray shirt, school uniforms
You don’t have to spend time thinking about what to wear if you have plenty of things to wear and they’re easy to find. They’re easy to find if you eliminate the things you don’t like to wear. They’re easy to find if everything has a place and everything’s in its place. You can also make it easy by taking pictures of yourself in different outfits so you can see what goes together – have those on display in your closet. It’s sort of like having a menu to choose from. You can put pictures of shoes on the outside of boxes so they’re easy to find.
Funeral suit: Get a funeral suit. Unfortunately, you’ll need it. When someone passes is not the best time to be heading to the store because you have nothing to wear. I learned this when my uncle passed at 98 years of age just one month before the pandemic hit. This was my second funeral in just a few months, and I made the comment I had to scramble to buy a new suit that would be appropriate
Wardrobe Makeover: Maybe consider hiring a consultant to give your wardrobe a makeover. After you’ve taken a stab at purging the unworn and ill-fitting items, they can help you have the more honest discussion about what you’ll actually wear and suggest a few articles of clothing you can buy to really upgrade your wardrobe. Notice the pattern here? Eliminate the unused items. Digitize the ones that you’re only keeping for sentimental reasons. Use the stuff that you still like but maybe had forgotten about. And upgrade by purchasing new and better items to replace some (but not necessarily all) of the ones you got rid of. If you can’t do it yourself, consider bringing in a pair of fresh eyes.
Valuable Real Estate: Some clothes in your closet are taking up valuable real estate. It’s not the highest and best use of that space. So move your vacation clothes somewhere else, maybe in a suitcase that you’re likely to use for vacation. Have another empty suitcase? Why not fill it with unused dress clothes if you’re currently working from home, wearing pajamas, and unlikely to wear a suit for the foreseeable future.