Shopping in the UK for womens clothes comes very naturally to me. I've escorted girls/women while they've shopped for many years. In fact I'm much more comfortable in a womans shop than a man's.
I've completely dressed as a girl, several times while I was young, with fresh tight skin. (Tranny mode). Older and wiser, I realise the thing I liked most, was the feeling of constriction in what I was wearing. Never with a corset, but long bra and panty girdle with suspenders and hose .... Wow, what a sensation! So I too like tight skirts, and tight tops, and that means cross-dressing of course. Shoes with a heel are a must. I don't wear skirts out, but I do wear high heels out.
Over the last couple of years I've gotten interested in 'dressing up' again. Not actually done it, but been out shopping for bits. Bought a dress in a town where less-than-manly-men would have been very unwelcome. I just asked if the dress could be returned if it didn't fit. (Yes, you have 14 days.) It fitted, and I still have it.
Bought foundation wear from Matalan and Primark. Always a gamble because this stuff can't be returned. Fortunately, it was cheap, and most of it fitted.
Not had a blink from anyone. Worst situations are returns to store. Often, to prevent fraud (?) your personal details are required. I pay cash, and provide an old address and a name not unlike mine. Had to return this lovey dress to Miss Selfridge recently. (Didn't want to, but couldn't justify the cost given how likely it was to get used.) I had all the "she couldn't get it over her head" reason for return planned. Wasn't asked a thing. In fact I was able to have a giggle with the assistant, because she made a sarcastic comment to her colleague that went right over his head. It was all, very very easy.
As others have said, it really is about confidence. Someone stop me buying tights at Tesco? Could never happen. I even took some back to Wilkinsons two years ago, with a complaint that they weren't fit for purpose. I got the refund, without ANY remark about who they weren't fit for ....
You will see this written many times about this cross-dressing lark. We are our ourselves, our biggest problem when it comes to dealing with others. I'm getting too old to care/worry what others think about my style choices. Sounds a bit morbid but ... I don't want to go to my grave thinking; "I wish I'd done this, I wish I'd done that." Especially since the only stopper, is me. As others have already mentioned, my money is as good as anyones, and shop keepers would prefer my money in their till than in my pocket.
Sadly, my immediate regret is taking that Miss Selfridge dress back.
Really looked good!