Quantity vs. Quality

Whenever I read articles in magazines about "streamlining your wardrobe" or "the investment pieces every woman should own," they regularly recommend buying fewer, more expensive items. The term investment piece kind of says it all, right? It's an investment, something that will somehow pay dividends in the future.
The thing is, I hate spending a lot of money on one item. Sure, that item might be amazing, but for the cost of, say, a Marc by Marc Jacobs handbag, I can have two vintage dresses, a pair of shoes, a new lipstick, a cute headband, get a haircut, go out to a nice dinner, and do a couple of other things as well. I can't help but feel like I'll get more satisfaction over having a lot of shiny new things to play with than just one.
I think I have a good eye for quality, and since I take good care of my clothes even cheap things tend to last. I did once tell someone that my superpower is finding the most expensive looking item in forever21, and that's actually pretty true. I'm willing to put a lot of time and effort into combing the internet and my local stores for the best deals.

This 1960s shift dress was only $16 at Vintage Underground, my local vintage store of choice. 
The problem with that is that sometimes I end up compromising. When I'm shopping I usually have a pretty specific idea about what I want - a below the knee white skirt full enough to fit a petticoat, or a plain baby blue dress with short sleeves or no sleeves. And sometimes I find precisely what I want, but if it's more than what I want to spend, I'll end up with something that fits my price, but not my vision. Maybe that white skirt ends up being pink, or the dress is printed with long sleeves. Often enough, I'll still absolutely love what I've bought, but then all of the ideas that I had about what to do with the piece have to be reworked. I might even end up buying more new stuff to go with the item that I just bought.
It's a habit that I recognized years ago, and I really have tried to break it. I've told myself time and again that if I can't have the right thing, I shouldn't buy anything. My habits mean that sometimes my wardrobe wanders off on tangents. "Well, I bought this, and it wasn't quite what I was looking for but it was still really cute, so then I bought this to go with it, but then that was the only thing that I had to wear it with and it's so cute itself, so then I bought these..."
What makes it difficult to break the habit is that the only downside is that I always feel like I need to buy more things, and that's not really a downside because I like buying things.
I have a pretty nice wardrobe. I've definitely fallen in love with pieces and spent more than I should have, but who hasn't done that once in a while? That said, as a rule, I don't pay more than $100 for a dress or $60 for a skirt. The vintage market is kind of overpriced right now since there are more people out there competing for fewer items every year, but there is still great stuff for the taking if you put some time into it.

The skirt is the bottom of a beautiful 1940s suit that I got for $50, while the top was on sale for $10 in the men's department of Urban Outfitters.
While I definitely believe that there are pieces worth dropping extra money on, I just don't know if I'm the person to do it. I like having a large wardrobe with a lot of different options to suit whatever mood I'm in that day. And frankly, I think that's fine. I know that there's been a lot of pushback lately over fast fashion and a movement to get rid of extraneous items in your wardrobe, but I don't feel any guilt over buying the things that I love. Other people can choose quality over quantity, but I'm a pretty firm believer in the philosophy that more really is more.