It is horrible to admit but I am not a good person to answer this question . Unfortunately I am now on the wrong side of 60 and whilst I am exceptionally young for my age ,  and my attitudes and drive are very good , the simple fact remains --- part of me now  is my age .I grow more conservative and therefore less adventurous --- because it is not required .
Also I was never greatly fashion conscious at any point in my life . My Father was a teacher of Art all his working life and very successful .Given his age --- still alive and 95 yesterday !!!!!!---- it is hardly surprising that his greatest love was for the Italian high Renaissance period . His great heros were Leonardo , Michael Angelo , Raphael , Botticelli and later Rubens , Titian and others . Although I now find the great body of this work boring because of the limits on subject matter mainly , I am still influenced by the great truths held in this period . The Truths of perspective , structure ( the Golden Mean etc) colour harmony and co-ordination and the idea of a " painting strategy or the  point of a picture "
Truth tends to be eternal and the only test of truth is Time .
Therefore Fashion per se is not greatly important to me because my whole outlook is based on the greatest fashion --- one that has been dictated and produced and finally validated , by Time .
Therefore speaking sartorially ( Dictionaries , girls) , I believe in the importance of  tip top material quality and the use of master craftsmen to achieve a good cut and hence the best shape .
It is a simple fact that different colours and colour combinations suit different body and  face shapes differently and the hair colour dictates often which colours work best and which fail .
Fashion is not nearly as important to the vast majority of men as it is to women .
My tip to a woman is to be smart enough to find someone who has impeccable good taste and whom you can trust to talk to you with complete honesty and candour . Don't use your own judgement . You can only see your mirror reflection and that does not show how you look from the side or , more importantly for those with big bottoms , how you look from behind .
So talk , but listen carefully and be prepared to act on what a good judge tells you , and not on what you fondly imagine .
I know this first Post is much more general than you imagined might result or from what you wanted .
But my advice is the best .
Find some great role models --- I would suggest Audrey Hepburn and Sophia Loren .
They were both beautiful rather than just super attractive and they represent two basic different body shapes .
99% of the time their total presentation was faultless . It does not matter whether they had the brilliant taste or they employed people with great talent . The results are what counts and they were always outstanding .
Now , meditate on what it was that made these two women timeless ( the key word) fashion icons . Once you have mastered that problem and got others to interpret you in the same way , you will have found success and universal applause -- whether you are a true beauty or simply just an OK woman who has learned how to maximise her assets and play down her weaknesses .