In spite of running a war-torn country, there is one way in which Volodymyr Zelenskyy’s life is easier than mine: He does not have to stand in his closet and figure out an outfit to wear each day. Instead, he dons his olive-green sweatshirt with a Ukrainian trident on the chest, his cargo pants, and work boots, and off he goes. Whether he is meeting with European leaders, addressing the United States Congress, or posing with Jill and Joe at the White House, his outfit is good to go. That’s not how things work in my life as you will see from these five different thoughts about clothing.

If Your Clothes Were Never Trendy in the First Place, Do They Go Out of Style?

I was looking through my photos on social media recently and noticed snapshots from ten years ago. They showed me in clothing I still have in my closet today. Shortly after seeing that, I found a box of Jell-O in my cupboard with a 30 Dec 2013 expiration date. I immediately threw out the Jell-O, but do I likewise pitch the clothes? And what about that great sweater I wore to my granddaughter Lila’s baby naming in 2009 or the cute skirt from my daughter Lisa’s bridal shower a year earlier? Is this a good time for Goodwill or could I possibly still wear these things?

How Can I Own Five Black Sweaters, Yet Have None that Work with a New Dress?

I recently bought a sleeveless dress in a color that could be worn year-round. The salesperson was well-trained in selling add-on products, so she suggested I buy a black sweater to help the dress make it through cold weather. Of course, she brought me three to try on. It was amazing to see the Goldilocks phenomena as applied to clothing. One was too short, one was too long, and one was just right. In fact, it was a beauty! But, I didn’t buy it because I have five black cardigan sweaters at home. Surely, one of them would work with this new dress. But if you refer to this paragraph’s heading, you will see that was not the case. There was a problem with each one. Too dressy! Too casual! Too bulky! Too flimsy! Not the right shade of black! (Say what???!!!)

Unwilling to buy my sixth black sweater, I ended up returning the dress.

Suffice it to say I also have a problem with those five-or-so pairs of black slacks in my closet. They should look good with everything…but they don’t! Argh!!!

With My 71-Year-Old Faulty Memory, Should I Create a Spreadsheet of Outfits that Work?

I used to buy a brand of clothing for the kids when they were young. Two items — a top and a bottom — were packaged together and sold as a set. Thus, the bright blue in the shorts or pants matched the bright blue in the multi-colored floral or striped top.

Trying to replicate that plan for myself, I think of making a spreadsheet noting what works with what: This shirt with these pants and this cardigan if it’s chilly out. Oh, and remembering that friend who always looked great until I noticed her shoes, I would also have a column for which of the many pairs of black shoes in the closet work with the given outfit.

Is it any wonder I envy Volodymyr? This is exhausting!

(I recently traveled out of the country for ten days with three dozen folks. Our leader suggested we use a carry-on suitcase instead of checking a bag. She gave us the key to frugal packing: every top goes with every bottom! Clearly, that would never work for my wardrobe. Clearly, packing for a trip is a nightmare.)

This Outfit Makes Me Look Fat!

I remember once my mom gave my bubbie a dress for Mother’s Day. Bubbie ultimately instructed her to return it to the store because it made her look fat! I was probably 20 at the time, which made Mom 51 and Bubbie 76. I was astounded! Bubbie was still worrying about such things in her seventies?! How could that be? Now I understand.

What Will Others Think of My Get Up?

I wish I could type this in a smaller font so I don’t have to proclaim it so boldly, but there are certain outfits I would never wear with certain fancy-pants people because they are just not snazzy enough. This, of course, would include ten-year-old outfits. Meanwhile, my buddy Volodymyr hangs out with everyone, everywhere with no concern for couture. For him, clothes don’t make the man. The man makes the man. 

But I don’t think it works that way for women. It sure doesn’t for me. Instead I have this entire mishmash of feelings over getting dressed in the morning which leaves me to envy Volodymyr and to think these thoughts every time I see a photo of him in the newspaper.