Disclaimer: I don't own Teen Wolf. Which is terribly sad.
A/N: An AU. I love AUs. This one happened because of tumblr. I was asked to create a summary for an AU of any fandom so I came up with this AU, then I forgot about it. Then a picture of Hoechlin wearing one of the hats mentioned came up and I remembered and had to write it. But yeah, I hope you enjoy it.

Derek was glad that he and Laura didn't live too far away from each other, he could walk to her place and back whenever she had a problem. Like when her sink had broke. And her microwave. And when her door handle fell off. Laura was a leader, that was apparent, but she also had the worst luck with her household appliances, plumbing and electricity. Luckily Derek could usually fix them without much hassle.

He wasn't paying much attention to the people around him as he walked back to his apartment from her's, but then he heard a familiar laughter. Panic over taking him, he looked up and spotted Kate. Laura usually called her "that crazy ass insane ex and what the hell did you ever seen in her?" He always pointed out that when they started dating he didn't realize how psychotic she was. You date people to get to know them, and he got to know her. And her dungeon she had her basement, which she had locked him in for some torture and sex.

Which, yeah. No.

Never again.

What was Kate even doing in the area? Last he knew she moved across the country to torment other poor, unfortunate souls. Not that he was going to stop and chat with her, instead he ducked into the closest shop to hide out until she wasn't around.

Because he didn't trust her to obey the restraining order.

Derek blinked, waiting for his eyes to adjust to the dimmer lighting of the shop. Looking around he saw that it was some sort of hat shop. Shrugging, he stepped in to look around. The decor was over all calm, with neutral colors, but every so often, there was something out of place. A little spark of personality. A weird painting on the wall or a hat rack that was bright pink. The mesh of the neutral and the wild shouldn't have worked, but Derek thought it did.

While Derek was looking at some rather well made black hats, a kid skidded into the room. Actually, he wasn't a kid, but he had to have been in his early twenties if anything. "Customer! Hello. Greetings and salutations. Hi."

Derek raised his eyebrows, "Hey."

"Oh, looking at my black hats, I see. that's 'd look great in black hats. I figure. I mean," the kid started saying, arms moving about to add emphasis to words that didn't need any emphasis, "you look great right now in your black shirt and dark blue pants that oh my they hug don't they." He laughed nervously, "And that leather jacket is just- what I mean is. Hello and welcome to my shop. Anything I can help you with?"

Derek stared at him for a few seconds. This kid was something else. He also wished he'd risked running into Kate. Instead he got told that he was wearing tight pants. Lovely. "Your shop?"

The kid nodded, "Yeah, see, I'm Stiles?" He pointed to his name tag, which had gold star stickers all over it, "And that's the name of the shop? I also make all the hats myself, so if you want to order one, I do custom orders too. And I do kind of want to measure your head because it's a nice head. Well, your face. And other stuff." He licked his lips, "S'nice."

Did he just run from one crazy person to another? Fantastic. "I don't need a custom hat."

"And although you'd look smoking a black hat, and clearly it'd go with your attire," Stiles started, gesturing to Derek's clothes, "what you need is to mix it up. Add some color and stuff, because that could just make things pop, y'know? I know you know." He nodded.

"I think I'll stick with black." Derek said.

"No." Stiles replied, grabbing Derek's arm and pulling him further into the shop, "I mean, sure you can buy a black hat, but you must try on these other hats. And buy those as well. Because I think you could pull off the weird looking hats. They would look magical on you, y'know? Can I take your picture?"

"What?" Derek said, letting himself be pulled along.

"When you try on the hats? It's a thing I do. I promise I won't post your picture on Facebook." He paused before adding in the thoughtful tone, "Mostly because I couldn't tag it right as I don't know who you are, it'd be tagged something like 'Hot Dude With Eyebrows.'"

"I doubt that I'm your only customer with eyebrows." Derek said.

"Yeah, no, you're right." Stiles agreed, "But your eyebrows suit you more than most people's."

"Derek."

"What?" Stiles asked, his face contorting into something Derek didn't even know faces could do.

"That's my name." Derek sighed.

"Alright, coolio." Stiles grinned, "Hi Derek."

"If you say 'hi' to me one more time I'm going to punch you. In the face." Derek said.

"Kinky." Stiles winked, then his face went blank, "But not actually. Because I'm not into pain, so I would prefer if you didn't punch me in the face."

Well, that made Stiles' form of crazy better than Kate's. Which was a plus. "Then stop saying 'hi'." When Stiles' mouth started to open, he added, "Or any other form of greeting."

Stiles saluted, "Alright. Can do, Derek. But yes, meanwhile I have hats." He gestured to a counter that had the weirdest hats on it. "I think you'd look ravishing in these hats. I mean, I think you'd look ravishing in anything or nothing-" he paused and looked Derek up and down, "Yeah, you'd look amazing in nothing." shaking his head, he continued, "But you'd look good in this hats and oh God. Can you be my hat model? Like, try each hat on in the store and I'll take your picture and then people can see how great they can look, not that wearing my hats would make them look like you but still. You could be my model. Are you a model?"

"No." Derek said.

"No you won't be my model or no you aren't a model?" Stiles eyed him.

"I'm not a model." Derek said, "I teach calligraphy."

Stiles' eyebrows shot up, "Really? Wow. That's hot."

"You think that everything about me is hot." Derek mentioned.

"How did you know?" Stiles asked, shocked. Derek just raised an eyebrow. "Right well, it's true. Is it weird? I can maybe dial it back if you're weirded out."

"If it was an actual problem I would have taken my chances in running to my ex." Derek found himself saying, "She was on the street."

"Bad break up?" Stiles asked.

"Something like that." Derek said.

"Right. That's cool I guess." Stiles shrugged, then froze, "Oh God. You don't even want a hat do you? You came in here to avoid your ex which I hope is a guy so that I can at least know that you're into dudes but if it's a girl I can still hope that you're bi or something and not straight but as you said that the inability to not hit on you isn't a problem I don't think you're straight or you could be like, a really laid back guy who is into girls and doesn't want to beat up guys who hit on him-"

"Have you had that happen?" Derek asked, deciding that if he wanted to take part in conversation with Stiles he should just interrupt him.

"Huh?" Stiles asked.

Derek stared at him, "Have you been beaten up because you hit on the wrong guy?"

"Um." Stiles started, "Maybe? Not a big deal. As you can see, I didn't really learn the lesson they were trying teach which is good for me n' all."

Derek nodded as he picked up one of the hats. It was clearly a Christmas hat. And ugly. Derek wondered why anyone would even want to buy it for anything other than a gag gift. "Why is this one even out? It's June." He glared at it. It was a reindeer head, with green antlers, a red nose (does that make it Rudolf?) and a santa hat. The hat was wearing a hat. He didn't wait for a response as he put it on his head, ignoring the gasp from Stiles. "This is not becoming." He frowned and looked up at the hat.

Derek looked back at Stiles when he heard a 'click' and saw a camera being held up, blocking Stiles' face. "Are you being a model for me out of pity?" Stiles asked, "Because I want you to know that I can live with that."

Derek took the Christmas hat off and ignored Stiles, "Seriously, no one is going to buy this hat right now."

Stiles shrugged, "You never know. Especially if I post this picture up by the hat, someone will see that you wore it and then they have to buy it because you wore it. Like, it's the same concept as selling a used tissue on ebay because a celebrity used it. It's like that. Only with you and a hat I made."

"Did you make it on a dare?" Derek asked, crossing his arms.

"No. I did not." He grinned, "I made it to sell because this is how I will be able to afford my own private jet."

Derek blinked at him, "How come I get the feeling that you're not joking and you believe that crap?"

"Because I believe that crap." Stiles said, handing over another hat. It was a parrot. It had bright colors and a beak. And feathers. Some actual feathers. It sat on Derek's head, little feet looking like they were perched on his eyebrows. "I do not understand what made you make these hats."

Stiles shrugged as he took some pictures, "This corner is filled with the hats I made when I couldn't sleep. Which as you can see by how many there are, is often. I don't sleep well, which I never have. I'd stay up all the time researching new and interesting facts, but not doing my homework. Which actually helped out fine because like, legit, because of that I own this shop."

"What." Derek took off the parrot hat and glared at the parrot's eyes which were staring back.

"Yeah, this shop is mine. I bought it with my money that I won from some trivia thing that I only got correct because of me reading about random stuff in high school. And so I was on this game show and won lots of money." Stiles handed him a hat that had to be some sort of nightmareish abstract art.

It almost looked like a jester's hat mated with a werewolf and then Van Gogh painted it. But as a hat. Derek stared at it for a bit, not even sure how he was supposed to wear it. Stiles had a smile on, as he took it back from him and showed him how it went.

"And so you opened a hat shop?" Derek raised an eyebrow as Stiles took a picture.

"I like to make hats. Keeps me focused." Stiles shrugged, "It's hard for me to stay focused on things because of reasons. But I like to make hats and I'm good at it, so I opened a hat shop. Named it after myself because it's mine. I thought about something witty, but I couldn't think of anything short enough. But our tag line is: Any Stile of Hat. Because of my name and y'know styles of hats. I know, I'm so amazing for coming up with that."

Derek grunted in a positive tone. "Oh yeah. Of course."

Stiles nodded, "Listen, I heard you earlier, because I was listening, about you having an ex and that's why you hid out here and I understand if I'm annoying you, I annoy a lot of people. Did you know I don't actually have that many customers? Yeah, mostly Lydia asks for custom hats so she's like paying all of my bills. Or the bills that my prize money can't pay, y'know?"

"Is there a point?" Derek asked, raising an eyebrow.

Stiles pointed at him, "Yes. There is. Thank you for leading me there, man. Because I was trying to say that I bet your ex is gone and you can escape home on your own but also I just feel like I need to ask this because you've been a cool bi or straight gay, or I don't know, maybe you're pan or something, anyway, do you want to like date me or something? Unless you're seeing someone because I don't like it when people cheat, I am against cheating."

"Well that's good to know." Derek smiled slightly, "Glad that when we start being serious you won't cheat on me."

Stiles' mouth dropped open and his eyes grew, "When? When? Oh my God. When this is good. This means that you're agreeing to a date. Oh God. I am dating someone who is so far out of my league."

"Calm down, Stiles." Derek said, putting a hand on Stiles' shoulder.

"You can't tell me to calm down when you're still wearing that hat." Stiles gestured to the nightmare mesh of jester's hat, werewolves and Van Gough.

Derek growled and threw the hat off, "Now calm down."

"You do realize what you're getting into by agreeing to date me right?" Stiles asked, fondling the nightmare hat, "Because a lot of people don't seem to realize what is going to happen when they start to date me. Which is awesomeness, dude. That is what's going to happen. Most people can't handle it. But I bet you can. You and your eyebrows."

Derek sighed, "I think I realize. Don't worry."

"But I worry about things," Stiles started, "so many things really. It's a problem I have. Legit problem, okay and I just-"

Derek put his hand over Stiles' mouth, "Hush. I am going to buy one of those black fedoras. When I pay you, it will be with a bigger bill than I need and you will slip your number in with the change." He took his hand away when Stiles started to nod along, "You are going to feel smooth and-"

"Classy. I will feel classy." Stiles helped.

"Sure." Derek agreed, "You'll feel smooth and classy as you hand me the change with your number."

"And you're going to call me?" Stiles asked in a hopeful tone. "You're not just saying all of this so that when you turn me down you don't have to see my sad, lonely, and pathetic face, right? This isn't your way to escape, right?"

"I'll call you." Derek said, grabbing one of the black hats. "And I'll be seen in public with you as long as you aren't wearing one of your crazy hats."

"You know how to charm all the boys." Stiles laughed, handing over Derek's change, his number slipped inside.