WoW, this is a great question and a really hard one. Option A is definitely out. I bought two pair of Dicker knockoffs from Target a few years ago. One a duskier brown and the other a denim blue. My friend, who never wears shoes that she can't slip on, liked them so much she bought a blue pair. I ended up passing both along to her. I was wearing the blue pair when a little girl yanked her mom's hand and exclaimed, "She has cowgirl boots!" They were, however, supremely comfortable and practically free. Why would I want the real thing, then? Also, I don't like recognizable clothes. Some years back I had a black quilted tote with some golden metal decorative touches. Spotted it for a quarter. So useful to me that I actually wore it out. No brand name. But I hated when kids all over the neighborhood would yell at me designer names. Kids! And I live in an urban ghetto.
Generally, despite continual acquisition and purging (and spending very little), I am pretty happy with my clothes at any point in time. I also feel like I have Enough for most purposes and am aware that too much choice just promotes indecision and confusion.
When I had a lot more clothes, I had so many great options that it took me over an hour standing in front of my closet trying to identify the better choice. Now I can get dressed in ten minutes. I've come to think of new items added as I Want a New Toy. If you get too many at once, you forget to play with some of them.
Occasionally I will really long for a long gone item and wish I had it again. I would fantasize how wonderful it would be to have a personal shopper who would fetch me a duplicate or arrange to have an exact copy made. Kind of like Hollywood wardrobe department. But I realize that I am not my inner teenager and definitely not built like her.
If I had whatever item it was, it wouldn't have the same effect because wouldn't fit the same way.
So I guess I would spend to have the next items I've identified that I want, without having to wait to discover them or find a good sale. I'd like a few winter weight, sleeved dresses in luscious colors. Not a little black dress kind of gal, even though I love black. I like to stand out. I would be happy to have them all the same. Recently saw such a sheath dress - onlly defect was a plunging vertical slit - with a front pocket! Know immediately that this was my next goal. Hand in pocket in a dress that could be worn for cocktails. Yes! That's 100% me and I'm shocked I never thought of it. So could have something made or just a pocket added.
