Great topic
I also read a lot, spent hours on the websites and lookbooks and talk about fashion 24/7 but sometimes I don't feel myself very fashion forward,I feel like I can not apply all the things I've known.There are some reasons: I work at a very small office where what you wear is no big deal, very few people visits the office and there is no one to appreciate your apperance,on the other hand if I had a meeting I try to do my best to look good and I get a lot of compliments, I like it, but wearing your best and sitting at the office all day doesn't give me the inspration I need. I can hear some will say be nice for yourself but not everytime it works, a person (at least I) need outsider's appreciation.
The other reason is, I easily get cold and my city is really cold during winter,sometimes I wear stuff which keeps me warm other than stylish. Another reason, my office,my home and gym are close and I usually go to gym after work and mostly I walk a lot so walking a lot doesn't work with very high heels or your designer heels. If I have a car to office job, it would help me more to wear fashionable. More reasons to go ; I mostly be late in the mornings and sometimes all the things I've thrown doesn't look good I need more time, at the end I choose safer things to wear.
Last but not the least, I am a mix and match person, I also live in a budget thus I can not get all the things I want to. I do my shopping from high street shops like Topshop, Zara, H&M .. etc, they do have good clothes but I think having key pieces like bags,shoes,boots or fantastic coats from high fashion brands like YSL, Chloé,Fendi;Burberry Prorsum.. etc add a lot of value and sophisication to your
appereance. Oh one more, I think being a tall and slim person like models also help to be sensed as fashionable, as we see a lot of examples on models street style thread, most of them wear jeans and tshirts but they still look marvellous and very fashionista
Sorry my post may seem long and untidy but I think I made my point.