If you are going to be out as a cross dress dresser or transgender person I think it is very helpful to dress well. Not so much age appropriate as I don't think that matters anymore. But clothes that fit both your body shape and the occasion. First impressions make a big difference.
It can be hard to find clothes that fit. Amazon and other retailers have made it easier to find clothes that fit. They have found that the best way to handle sizing information is to include it in the pictures. When I first started looking for female clothes I'd go to Savers and try on anything that looked like it would fit, write down the labels, and search online to see where I could buy that brand.
I found Carol Hochman that way. First thing I do is check the clearance section. Why not try a sale item or two to see how it fits? The Carol Hochman top I bought at Savers has tiny buttons. They don't do that anymore.
It may help to read online fashion advice for the Inverted Triangle body shape if you are the typical cross dresser. It took a ton of work with diet, exercise, and favorable genes that I have the coveted hourglass body shape. 24 inch waist and 34 inch hips.
Marion