Simples...

I'm sorry to quote a meerkat but there are times when it is too easy to over complicate and become wrapped up in making style (which is fundamentally different from fashion) more complicated than it needs to be.
Fashion is complicated there are allegiances, multi faceted looks with historical references to lines of the past, there are egos in play that must be satisfied and there is always the smallest feeling that whilst the Emperor may not be without clothes, the ones he does have, are well a bit weird.  Fashion is about trend and a fundamental understanding of what you should and should not wear, it's about magazines full of glossy girls and wind machines.  I have a deep seated and unshakeable love of fashion but it's not what I go to my wardrobe every morning to wear.
For this I look to style and that lives in the realm of elegant simplicity.  It is about balancing function and fashion, as well as to a certain extent knowing your limitations or putting the tools in place that ensure you're limitations are not only minimised but start to work to your advantage.  So with this in mind lets talk limitations and simple fixes.

1. I can't walk in heels
This is a skill and like all skills if you want to you can learn how, through trial and error, or through the time saving and sensible option - find someone to teach you. www.perfectlypoised.co.uk currently in Bristol but I'm pretty sure it's about to role out over the globe, this is one service that I absolutely say is worth jumping on the band wagon.  There is nothing less stylish than tottering and there is nothing more depressing than constantly trying to wear something that you can't.  How many pairs of shoes in your cupboard collect dust, rather than memories? However if you can't wear heels for medical reasons it's not a disaster, a flat shoe can be as, if not more beautiful than a heel, it's just about making the right choice for you and your feet.

2. I've put on/lost weight
Firstly you need to look at the hard truth, can you change the current state of affairs?  If your clothes are hanging off you, is that what you wanted to happen?  If your clothes are digging into you, do you have the time or the inclination to undertake the necessary steps to fix it?  If it is what it is, then you need to build yourself a new wardrobe that makes you feel comfortable in your skin again.  The key to feeling stylish is accepting who and indeed what you are.  If you do want to return to your previous size then do yourself a favour, buy 1 thing that truly fits you now and makes you feel great - to give you the confidence and impetus to get back to feeling as you should.  It will also work as a first step, everything has to have a start and I truly believe that starting on a treat or positive works.  Notice I didn't say feeling like you used to, that ship has sailed, even if you return to the same size you will feel differently about it.  Never try to go backwards, it's harder. (Anyone who's ever seen me reverse will tell you how hard)

3. I'm out of proportion
Rubbish!  You are perfectly proportioned you just need to teach yourself a few tricks.  The worst thing you can do is actively try to hide things, it never works out.  If you throw a tarp over an elephant, it still looks like an elephant.  But if you set off fireworks on the other side of the room, People ask, "What Elephant?"  Draw attention away from the things you don't like, to the things you do.  The art of illusion is your best friend.  Personally, I would prefer if no one noticed the fact that thanks to significant weight loss my lower stomach is comprised of the excess skin that used to cover my expansive torso (please excuse the graphic description), so I wear higher waisted jeans and have accepted that tight t shirts are not my friend.  I draw the audiences focus higher, I don't wear nothing but baggy tents that hang from the neck, so that my entire body is covered and then looks bigger.

4. I hate my legs/arms/boobs

See answer to number 3, oh and get over it!  There is nothing wrong with your body, it's yours.  I know,  I've gone too far in the keeping it simple.  There is not a person alive without a legitimate complaint but having said that there aren't many things that can't be overcome in some way and the first and easiest step is to stop hating what you can't change - it takes so much energy which could be used elsewhere, like finding a solution.

5. I don't know where to shop

A common complaint from every client I have ever had.  We go where we are comfortable and as a result miss so many opportunities.  Indulge me for a moment, if each shop has 500 different items of clothing in them and a single High Street has 5 shops that service your gender, that's 2500 options or possibilities.  "That sounds like a lot of effort to find something."  You're right but if you are reading this you have internet access, which means you can shop in your PJ's, which is no effort at all and there are a list of sites on here which have amazing clothes and easy return policies.  Go somewhere different!  It's the easiest way to get yourself out of a rut.

Think of your "limitations" as opportunities.  Style is at it's best when you choose your own, whatever it may be.  It is the act of making the choice that will help you achieve a style.