It sounds as though your wife has given you a lot of the same kind of help, support, and advice that Phoebe gives me. We love to shop together. We watch for things that would go well on the other, as well as for ourselves. I laughed when your wife said some of her clothes came from the Good Will store.
We have Good Wills, but we do most of our shopping in more upscale stores called, Value Village, a large Washington chain that sorts its used clothes by size so you don't have hunt through the whole rack to find things that fit. We have also gone to consignment clothing stores where they often have really nice stuff, but at higher prices. I don't buy anything much from catalogs because I so frequently find that things labeled for my size really don't fit when I try it on.
I hope this letter gets to you before you buy your wig. Wigs can make a crucial difference, not only in your ability to pass, but in conveying the personality you want to project. Some of our Emerald City members make the mistake of buying wigs with too much hair--wigs that an 18 years old girl might love, but which are simply unbelievable for someone close to our age [60]. Also most cheap wigs really look cheap, and often they don't hold their shape long. The good ones usually sell for $90 to $100 and they are worth the investment if you buy them from someone who really specializes in fitting, styling, and selling wigs--only. People who service the chemo-therapy group are often very good at this. Avoid human hair wigs; they are hard to manage, won't stay curled, and aren't as nice looking as the good synthetic ones. Look for one with more than one shade of hair strands--the good ones are a blend.
Jim Bridges does sell wigs when he's at a conference, but even there, you need to be sure you get a light, fluffy thing that looks really nice with your face. Shop with make up on, or try to find a place that will do the make up along with the wig fitting; otherwise you are less likely to find something that continues to really satisfy you.
We have a shop in Bremmerton where many of us buy our wigs. Margie King runs it as "King Imports"; she trims them, instructs customers on how to care for them (even has a video tape she loans), and gives lots of good tips to us. She loves to work with TV's; says they are the most polite people who come into the shop, even though she delights in teasing us.
Phoebe has bought me a couple of wigs there for birthdays, and I have bought a couple for Phoebe. She enjoys wearing wigs too, though usually only one at a time. Unfortunately our heads are very different sizes, or we could probably trade off, like we do with our jewelry. Everybody wants to sell wig picks, and brushes with plastic spheres on the end of each bristle. The best wig brushes we have found are cheap plastic brushes with metal bristles mounted in a rubber base. They will comb it out, or lift it up and arrange it; but they slide in and out without disturbing the rest of the hair nearby.
You mention that you like short skirts and your wife thinks long ones look better on you. The most ludicrous sights we see among our local TV's is when some of them go out and buy a stretchy party dress that clings to their figures and ends up at the bottom fold of their rumps. At best those dresses and short skirts look nice on sixteen-to-eighteen-year-olds, But when middle aged men or women put them on, they are very badly out of taste. Your wife is right! Look around at what the ladies in your office and other offices wear--not the ones right out of high school, but the ones near your own age. (I used to do that until there were none my age.) Concentrate on the ones whom you think look really nice--who dress with class and style. Set your own goals to dress with class and dignity, and you'll never be wrong; and you'll not embarrass your wife when you're out together. And when you set your goals to look like a smart business woman your age, you'll be much more satisfied with your appearance, because you can achieve what you want.
When we are just beginning to pick women's clothes for ourselves, we are sometimes unaware of how little we really have noticed about what women wear for different occasions. But your wife and Phoebe have been concerned with these issues all their lives. Phoebe has been of inestimable help to me in saying, "No, that's the wrong age; the wrong style for your body; the wrong match of top and bottom for best appearance. (Of course you don't have the body problem I have. Since I have retired, I have gained a lot of weight that I'm now trying to get off. So I'm now mainly dressing in big shirts and slacks as Allison. They can still look very feminine, but svelte is at the other magnetic pole.)