I started writing a long rambling story but realized that I need to get to my ironing.
V - what you are talking about is the "wrapping" and how it was viewed by the G. I think that for many of us, including myself that we allow our self image to be formed by the opinions of others. And given that those others have an interest in keeping us down so that we don't look up that can be a tough hill to climb. I know that for me at the time of "bomb-day" I did actually believe that no other woman could be interested in me unless they saw my pay packet. I've been fortunate that I have had people around me since who have been a mirror to let me know that "the looks decent wagon didn't pass me by".
I myself have a strong belief in the merits of good tailoring. It is a significant investment but a well made piece of clothing will far outlast any discount priced goods. I have some very nice Egyptian cotton shirts that are just about to be ironed that are several years old and show no signs at all of wear. I used to buy cheap and would be lucky to have a shirt last a year.
The first and most important thing about clothes (and yes - a man is lecturing about clothes to a woman ) is fit. The second is also fit. Colour and style, the first being more important come way down the list.
I know for men's clothes that it is so much easier to get them altered to get a good fit but perhaps look around. A few nice pieces with accessories will last you years and allow you to look fabulous for a modest investment. Maybe check to see if there are any tailors / seamstresses around. I get the impression that you have theatrical connections which may help get you pointed.
Just my 2 pence.
On BD H52, W50 T27, M26 S21, D23 BD-9-Mar-16 D-15-Jan-18 Final-19-Apr-18 I am a storyteller. The story may do you no good. But a story is never for the listener. It is always for the one who tells