Perhaps we could make this thread a "how I got into fashion" and "why am I interested in fashion" stories thread? Those are fun to read
@paislexy I hope you're not trolling, because I'm going to answer as if you aren't and probably embarrass myself a bit.
The first thing I'd do is put aside the idea that fashion is all about looking good or looking attractive. It's certainly an important part of fashion, but it's not the sole point.
An ok place to begin learning about fashion is
craftsmanship in classic menswear, because it's fairly straightforward, but will expand your understanding of fashion beyond "looking good." The classic menswear aesthetic is not too weird and won't provoke that "wtf is this frivolous extravagance" gut reaction - it is easier to understand why someone would pay thousands of dollars to look sharp in a suit than it is to understand why someone would pay thousands of dollars to look like a goth ninja or an anime character or a giant pile of blankets.
Here are some posts and blogs on classic menswear to begin with.
n.b. I don't know that much about classic menswear helpppEven if you don't like suits and wouldn't wear them ever, you can still appreciate the skill and effort that goes into making them, and perhaps expand your understanding of fashion. However, the culture that surrounds classic menswear can be too focused on craftsmanship, which is also only one facet of fashion :/
Another thing to consider is that "looking good" is not some sort of static ideal everyone shares, but a fairly arbitrary product of culture. Men have worn high heels. Men have worn skin-tight tights to emphasise their manly calves. Women have worn giant bejewelled shoulder pads. Women have worn skirt frames to create the illusion of large bottoms. What looks good is always changing, never constant. Yohji Yamamoto, a Japanese man born during WWII, is going to have a very different idea of what "looks good" to Hedi Slimane, a French man who grew up with rock and punk, and they are both going to have a different idea of what "looks good" to you.
If you want a better understanding of unusual design, you first have to expand your idea of what "looks good" and squash your natural desire to dismiss things you don't understand. Read about contexts, histories of clothes, histories of brands, backgrounds of designers, environment, foreign culture, etc. It is useful to look at wikipedia, the vogue encyclopaedia, style.com and forums like ct, styleforum and stylezeitgeist.
Appreciation of fashion and design is not necessarily related to whether or not you would wear it. I admire how Ann Demeulemeester skilfully constructs dark romantic moods, but I am not interested in wearing her clothes because I want to look relaxed and cozy.
The Cutting Class is a good blog that highlights how designers use techniques to create visual effects.
If you're actually more interested in the looking good/dressing yourself part of fashion, then
r/malefashionadvice's sidebar and the subreddit as a whole is an good place to start.
there was a great overview of Raf Simons' work on Hapsical's blog that would be really nice to show people but it's gone now :(((Edit: o: thank you germinal
http://care-tags.org/viewtopic.php?f=2&t=61&p=38012#p38012 <--- Raf Simons overview by Hapsical