It absolutely will get easier, but there will be times when it will still be uncomfortable for one reason or another. Don't beat yourself up over that. Don't tell yourself that you should be past it or whatever. It's going to happen from time to time.
The last time I shopped for a suit (which for me personally, is the hard one for various reasons -- underwear is easy), the male salesclerk pretty openly snickered at me. Initially he was on the phone with someone and he would look over at me then make some comment into the phone that I couldn't hear. After a few moments he was off the phone and female staff person came over and the two of them stood behind the counter, watching me, half-whispering to each other and cracking up. Neither of them ever spoke to me. I was humiliated and left.
This was 7 or so years ago and I would probably handle it differently now. In part I think I reacted the way I did because it was the first time I had been so openly mocked by sales staff when I was shopping for clothes and I just wasn't expecting it. Sure, I'd gotten some weird looks before, but that was the extent of it. If it were to happen now, I would be a little better prepared for it, I think. So keep that in mind too, uncomfortable situations will happen but you will get better over time at handling them.
I still don't own a suit, but I am thinking about getting one.
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