Contradicting fashion style

Hello everybody! The other day, I had a little discussion with a friend of mine concerning wardrobe change ~ it mostly consisted of whining about not having money or right models. We are pretty much in the same shoes...in need of a change, but lacking money. And there is probably lots of others with the same problem. So how do we accomplish our much needed change? Will the day when we burn all the old rags ~ in reality send them to a charity or younger cousins ~ come?

Always being a bit of an outcast caused me to try to stand out and not follow trends. And since I'm usually an awkward human being, clothes was my way to express my uniqueness. And with it I would try to show my attitude, emotions, the mood I'm in...
To introduce myself better to you, these are my...let's call it summer wish lists.

I would very much feel comfortable wearing biker boots, leather jackets and trousers. Riding a motorbike, trying to look intimidating. And I feel like this style suits well with my personality as independent, free, don't ya mess with me attitude...could be sexy. Being a young woman, I think this style would fit me and wouldn't interfere with the career path I'm taking.

I did mention that I dress based on what mood I'm in, and usually it's between a confident and a girly girl. I've been having googly eyes over this dresses for ages now! I just find something charming in the 50s fashion. I like that they are not too long or short if you have body issues like I do and would look perfect with some cute shoes and perhaps a hat. Exactly what we need for warm days!

I understand that girls nowadays don't typically wear clothes like this, mostly short shorts and a tank top. But then there's me...giving my best to try and stand out because blending in is overrated.
Fashion can be difficult, right?

Anyways, hope I didn't bore you ti death already! Wish you have a lovely day!