Sal, I am sorry about all the stress you feel, and about the loss of your mother. My heart goes out to you.
Regarding your winter style, I think you have got some good advice in this thread. However, I would like to add a few suggestions: How about getting some long-sleeved solid crewneck or V-pullovers that you could use as tops in winter and perhaps in spring and fall, too? If you don't like bulky layers, you could just wear a cami underneath. But of course, if it is really cold, you could add a topper like a blazer or cardigan. Items like scarves and necklaces are easy to wear on solid pullovers and can offer some variety from day to day. And consider looking for a printed skirt and/or printed trousers. The print could be floral, geometrical, abstract or anything else you prefer.
Of course, you don't need to dress in all black or navy just because it's winter. We have seen you looking great in colours like camel/toffee, red/coral and blue/aqua. You probably have additional "happy colours." Try to include at least one of your favourite colours in each outfit, for example in a print, a top, or a scarf. They can help to lift your spirits--often particular important in winter.
Personally, I have felt that my winter wardrobe was becoming too neutral/dark and included too many heavy/bulky items. So last winter, I added a few non-neutral toppers--among them are three long (sleek) cardigans that are wonderfully comfortable, spark joy colourwise and can be dressed up or down and used for virtually all my activities. (They are, for instance, easy to wear with a column of colour in any neutral shade. ) This season, I decided to let some heavy/bulky winter items go and to add more thin wool underwear instead. I feel quite happy with these adjustments. By the way, making sure I have some non-neutral footwear is essential to my style all year round.