OK, I'll bite. I didn't read every post so if I repeat, consider it affirmation for the prior reference. -
(1) Don't Panic Buy. "I have a wedding to attend this weekend and have nothing appropriate." This scenario breeds disaster, believe me I know. (As an aside, next time you are at a wedding or other mild dress event, you can easily pick out everyone who panic bought as easily as everyone who hasn't bought anything since the last time they panic bought!) Look for complimentary clothes when you don't have anything on the line so that you have time to try them on and think about them at home. Don't be afraid to solicit advice from the the store personnel on your choices either. If you go in on a Wednesday afternoon when nothing is happening, they will act as your concierge lining items up for you to try.
(2) Buy Fitted Shirts - Even if you are overweight, make sure your shirt fits you. (And if you are overweight, nothing looks worse than a non-fitted tent. If anything it compounds the look you are trying to avoid.) A well fitted shirt will make you look sleeker and more fit. They are also more comfortable to wear especially if you are going to be in it for awhile.
(3) Buy The Best Shirts You Can Afford (and have your favorites dry-cleaned) - A well-made shirt will nearly outlast you if well cared for. Also, for the ones you wash, rather than putting them in the dryer let them air dry. Even in humid climes it is usually dry by midday.
(4) Have Yourself Measured - "Oh, I'm a large." So, you buy anything with an "L" on it unthinkingly. That's what I did until I finally got measured and discovered I am a tweener & really need to try on everything to be sure it fits me rather than me to it. Before I did this I would always end up with a number of things that I would secretly dread wearing. So it goes.....
(5) Utility Clothes Rock! - Dickies & Carhart make some great stuff that wears like iron and looks great, better if you have them tailored. (No, I'm not kidding!) They are usually stocked in the back of Sears, Penneys, Wally World or in a standalone store. Dig through what they have & see if there is something that suits you. You would be surprised at some of the great styles they have where you might expect just functionality. I found a trick black Dickies quilted Mao jacket that gets a "Wow!" everytime I wear it as well as a "Where did you get it?". Best $19 I've spent on clothes.
(6) Shoes & Boots - I work with a Russian emigre. She had some pretty hip shoes on one day and I asked her about them. They were Russian and she told me that they cost her nearly a months pay in Russia. She told me that they were nearly 10 years old (they did not look it) and were extremely well made so that they did not need to be replaced. That puzzled me a bit until her next comment which really stuck. "I was too poor to buy low quality shoes." In other words, throwaway goods were the province of the wealthy but she could not afford such a frivolity. I try to apply that across everything not just shoes.
(7) I Like Wool - Except for mild dress & up, as long as the weather is cool I am usually wearing wool socks. They are available in such a variety from thin to thick that you can get different weights depending on the weather. Buy them at well stocked outdoor/camping stores. You will be amazed at the variety and how long they last. They do not tend to pill, at least none that I've bought have, look no different from regular dress socks, and tend to have more padding in potential rub areas. Even if you are not on your feet a lot, they are more comfortable. Plus, if you ever have an impromptu where shoes come off, you will never be embarrassed by how your socks look.
Hopefully there is something useful here.
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