Stepping out of the changing room, Harry resisted the urge to shake his leg or pick at the problem fabric just inside his trousers. Magical underwear just wasn't going to happen as far as he was concerned; they were all baggy and had buttons or draw-strings, so it was like wearing small swimming suits under your clothes and probably would've been really uncomfortable unless you were wearing those 'full robes' Madam Malkin had mentioned.
The non-magical version she carried wasn't much better. She only had the one kind, something most like what older wizards would be used to, but they were loose too and had little legs on them. They weren't boxers, but they weren't briefs either; Harry didn't know what to call them except odd. They were uncomfortable too, bunching up in all the most awkward of places and even once you got them sorted out they still felt like they were about to do it again.
Still, he had needed them, and without any muggle money and no means to get around London on his own, Harry supposed they'd have to do. He certainly wasn't going back to Gringotts just to get some, only to end up with them riffling through his memories or yammer on about investments and law until he missed yet another lunch. Opening an account for Hermione today had been bad enough.
His trousers were a different matter. Though they were muggle, they weren't jeans; they looked like khakis… only black. Briefly Harry wondered how the Weasleys had gotten jeans for Ron in the first place, but then felt bad about wondering just how little money the family actually had. They'd been nice enough to take him in when he didn't have anywhere else to go and thinking of them that way was a poor repayment for it.
That was actually the reason he was going to donate his robes from last year in the first place. Ron was taller than him and they had already gotten their things for this year, but there's always next year and Ginny. He could afford to buy new things and donating his stuff meant there were cheaper options available for people who couldn't - as long as he kept his name out of it that is. Things might change for them if Mrs. Weasley did go for that job, but it was still good to help out.
He had decided not to go for green, at least not for his trousers and robes, only for his shirt, which was all of one color, the color Hermione had said would look good on him. Madam Malkin had managed to talk him into a darker forest green to wear later on for robes and trousers once he had gotten used to the idea, just to try it out. She had offered him a discount and he thought it'd be rude to say no.
Everything he had ever worn outside of his Hogwarts clothes had always been drab and colorless - mostly blacks, grays, and whites unless they were Dudley's worn-out or ripped-up cast-offs - so he didn't really have a lot of experience being a person of color. With color, Harry mentally revised; a person who wore color. He didn't know what it was like being a colorful person; that was better.
Even if he wore something like this every day it'd could still probably take him until their first real date to work up to it, and that was still a year away. As much fun as being with Hermione has been, and as well as it's been going, part of it was because this wasn't a date - it was practice.
Even though things had gotten rushed and fuzzy when he asked her out, he was pretty sure this was still not really a date. He had only been asking about Hogsmeade, he was pretty sure of that, so there was no doubt that Hogsmeade was the official start of things - unless he got sick and threw up all over her shoes, in which case he have to hope she felt sorry for him and let him have a mulligan.
Harry looked into the nearby mirror and tried to flatten his hair again as he debated whether he should tuck in his shirt or not. Whenever Aunt Petunia made his cousin Dudley dress nicely she had always made him tuck it in and wear a belt. Madam Malkin didn't carry belts though out of fear people would take them for ties and choke themselves; there were few enough wizards as it was, she said.
"Now there we are," Madam Malkin said appreciatively as she looked up from bagging his things. There were two bags full of clothes; Harry hadn't realized how much he must have been working Mrs. Weasley overtime. "When you asked for muggle things I must say I was rather doubtful, but that's a nice blend of the two."
Harry had to agree, and it seemed functional. The trousers, socks, and odd underthings may have been muggle but they went well with the wizarding shoes and shirt, which was nearly indistinguishable from a muggle one except for not having a brand name or the annoying tag in the back. The robe was basically nothing more than a long black light-weight jacket with pockets. Several pockets. It even had deep pockets inside the sleeves for some reason. He had decided against going with anything with a hood, and if he took the robe off entirely then he could easily blend in with a non-magical crowd.
"That should be you all sorted out," the shopkeeper said as she tallied up the bill again on a small notebook. "Now we can see if the new payment system the goblins had will work. You've got better things to do than spending all day talking to us," she said with a wink before turning to take the bags to the front.