I can relate to this entry a lot, I too went through different fashion stages including goth and lolita. I think knowing what overall aesthetic you want to achieve is the main hurdle, and once your over that it can become much easier, as you know what is going to work for you instead of buying blindly. I've never gotten into Pinterest before, but I do like your idea of pinning styles and items you like, I may have to give that a try myself!

I'm pretty much at the same stage with my own wardrobe. I've taken out everything that just doesn't get worn or that doesn't fit anymore, and am now trying to work out what kind of clothing I would a) need and b) really like to wear. I'm also in a similar position with money: a poor student cannot spend all her money on clothing.

My strategies in handling this are flea markets and sewing. There's a brilliant flea market near where I live, in a rather posh part of town, where all the old ladies go and sell their old, super high quality clothes (just today I bought a lovely off-white, pure wool sweater there for pennies!) mostly for very affordable prices.
I'm not awesome with the sewing machine, but I can do basic dresses, skirts and blouses, and for this purpose I've been taking apart some of my older clothing which I just don't wear anymore (or never really did) but which are made of fabrics that I really like. Hoping to get some nice new summer clothes out of them...

One day I too hope to be able to do that "effortlessly wonderfully put together" -thing some people are so good at. My problem seems to be accessorizing, I simply cannot figure out how to it well! Oh, some day...

Though some of my tastes (within the vintage spectrum) have changed here and there over the years, for the most part I've loved many of the same things for ages now, so for me it's been a matter of continually working to build a well rounded wardrobe (aka, not just cute dresses! :)). I really put the emphasis on doing this in 2012, in no small part because we were, at the time, moving across the country from Ontario in the east to my home province of British Columbia on the west coast and I knew that with the move would a considerably busier social life (and I didn't want it to look like I only had a few outfits).

I made a thorough inventory of what I had, what key pieces were missing, and a few "wish list" wants, and set off (over the course of many months, don't get me wrong) to fill in as many of gaps as possible. With luck, patience, and some solid investing (with funds largely raised from selling off some other non-fashion items I could live without), I filled in most of those gaps and have found that as a result getting dressed has, by and large, been substantially easier (not that it was hard per se before, but having more of my wardrobe basics covered made it even more of a breeze) and more enjoyable ever since. It sounds like you're on the same kind of path to reach that end goal, too, honey, and I wish you all the luck in the world with it!

♥ Jessica

I can really relate to this too, although I occasionally like modern fashions, I never feel right wearing them. Since i've been wearing vintage clothing, mostly 40s style, I have felt so much more comfortable and myself. As much as I would love to wear genuine vintage items my budget just doesn't allow so I have to resort to reproduction! There are some bargains about though if you persevere, I recently bought two beautiful 40s style summer dresses for £11 and £12, so keep looking and i'm sure your wardrobe will come together!

First I haven't looking for my style a long time... when I was a teenage girl I weared a lot of clothes that my friends didn't want like leopard derby shoes...But I remember that Black was the ultimate color !!! Finally the accessories were my colors's touch.
Today my style is inked in my heart and it's a rainbow in my wardrobe with most red, yellow and teal things and 50's... But here, in France to find vintage clothes or reproduction is very difficult, maybe if you live in Paris, you have more chance... Here only 70's and 80's are represented an it's not my way.
So one day I've decided to sew (another reason is my "pearbody"... no way to find something in this world with skinny or slim clothes... and my size too). So now I found my happiness in Colette's pattern, sometimes Burda, Vintage Butterick or Vogue.... and I knit too (my Knit for victory is one of my "subjets"). And thank you Internet to permit me to buy my shoes in England....
Like you I look at the pinterest wardrobe and yes sometimes I find marvellous things but too expensive. My problem with Fashion in general is that people are copy and when you sew too because if it's "great" to wear the last pattern... ok with not the same fabrics or colors...but sometimes it's same, like twins... because in Fabric "land" you have fashion too...
I'm really sorry if my language is difficult to understand but I'm french and I've returned to school since january...