Wow, the advice/opinions are amazing here. Well, I now have some new goals;
-- to start wearing my nicer clothes NOW. I have experienced saving something for special times only to find it doesn't fit or is out of style as mentioned here. So no more of that.
-- I'm going to purge my closet even more ruthlessly to weed out the mundane, mediocre, flat, items that I wear because they are safe to ruin, but don't feel good wearing.
-- I'm going to only buy clothing that fits my lifestyle. I am still guilty of buying for a lifestyle that I don't live anymore.
-- I will buy better pieces that suit the task. No need to buy a beautiful silk blouse for walking in the park, but yes to buying a nice fitting updated cool relevant exquisite cotton t-shirt that's in my budget and that can stand up to the task.
-- I am going to put together some outfits based on my activities so I don't get so frustrated in the morning trying to figure out what to wear and then end up wearing the same old boring safe things. I'm a mood dresser, so I'll need to have several to choose from at each activity point.
-- I will strive to believe that I'm worth it to wear nicer things and not hear my mother telling me "don't wear that, you could ruin it" The answer to that is "Yes, but I can fix it, or buy another one" As pointed out by some of you, these are clothes not precious jewels. They need to work for me, not the other way around. This all needs to be comfortable and fun. (with maybe a bit of a stretch at first).
--Continue to seek advise here on this board as you are all amazing and so very helpful!!!