There is definitely an issue with choosing clothing items at the tailor shop, at least for me. It's been an issue for some time. Once in a while it works perfectly, but the vast majority of the time nothing will appear when I want to resize an outfit that I'm not currently wearing.
To get around it I click the heading at the top that says Wardrobe List (I think), and from there a Strip option will appear. If I strip completely and then go back to the tailor all of the items that can be resized will be listed properly.
I've also noticed another wardrobe issue that started with one of the more recent game updates. When I start a new game I create and save a School Uniform outfit, that has me wearing the default school uniform, shoes, coat and underwear. After that point if I enter the wardrobe and attempt to wear that saved outfit the school uniform refuses to appear as the clothing that I wear. If I click the Clothing heading in the sidebar that normally shows an image of the clothes nothing shows up, and in the wardrobe itself the clothing item appears as a broken image link. I have to manually select the uniform from the available clothing in order to get it to appear properly. It's the only clothing item that I've had that problem with.