If you had to get rid of everything in your closet EXCEPT for one item, which item are you keeping and why? (bonus points if you add a picture)

You are living in the reality the former you created. Soon you will be living in a reality the current you is creating right now. Act accordingly. ~ Andy Frisella

I'm unsure how to best wear this sports jacket other than for a vampire or sci-fi cosplay event. It's a dark red leather jacket, three buttons and two pockets at the waist with two more slit pockets for slipping you hands into. I wore it one time before with a black polo but that didn't seem right to me. I have a heavy amount of western attire, so i would like to fit it in with that. But again the jacket does feel a bit futuristic to match with my old west style. Any thoughts are appreciated, thanks.

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I’m curious how others plan their clothing expenditure. Is it an annual percentage of your house hold income? A monthly amount? A seasonal amount? A spur of the moment thing (when I see what I like- I just buy it)? A wad of cash to the thrift store or mall (when it’s gone I’m done buying)? What’s your approach? I would like to tell you that as a financial advisor I have a well documented system but that simply isn’t true. Fortunately I worked in quality mens stores when I was 15-24 so I developed a sense of buying long lasting quality both in style and material yet my method is less systematic. Since joining this community I have attacked the economics of my wardrobe and thought I might share my journey to trigger discussions about your own: A year ago I went through my closet with a pen and pad and estimated that if I replaced everything of mine in there at today’s prices it would cost $40k. Some items are 30 yrs old. I even have a few 40 yr old items. So if I were to average 40k by say 25 years average life of each garment, thats $1600 per year or $133 per month. Full disclosure, I didn’t spend that much. I look for sales, some are gifts, and for the really old items I got the store discount. Furthermore all these numbers are extrapolated up to today’s price for example the shoes I wore yesterday are over 42 yrs old- today they would cost $850. They were $200 in the early 80s when I got a 40% discount so about $140: still a lot of money for a poor college student but clearly I’ve gotten my money’s worth. Also my career over 40 plus years has had big swings in income. It has been a long road of big feast followed by shallow famine. So I buy when I’m flush. Lastly I like to travel and buying things on trips helps me remember the trip every time I wear them. Recently I’ve been “blessing others” with poor fitting items. The most expensive clothes are those I won’t wear. So thats my journey. Basically when spending -what to me are bigger amounts (custom suits, quality shoes) I try to be ruthlessly timeless to exacerbate their value. My goal is to keep my outfit below a $6.00 per day average wearing costs by buying quality timeless style. The pics are the 1982 shoes and 1982 green tie I wore yesterday and the silver tie I wore in my wedding in 1985 that has been in one of my OOTDs