I tried:
"Are you certain you mother will like this, lad?"
Henry nodded. "I've seen her internet search history. She'll like it."
Hook arched an eyebrow at the foreign phrase.
The lad grinned. "Trust me, Hook. My Mom is gonna like it."
"Very well."
He glanced himself over in the looking glass. He thought he looked absurd. The trousers -jeans are what the lad called them- were extremely loose. The pockets were unusually tight; he couldn't comprehend what use they had beside decoration. He could hardly push his hand in one.
What is the purpose?
There was no way he'd be capable of concealing a small dagger in these jeans.
As for the shirt, well, the fabric was light. It'd never protect anyone from the harsh weather in this town. It was cut low but required no buttons. That part he didn't mind so much; however this shirt wouldn't offer a smidgen of protection if caught in a conflict. Any weapon, even a fist, would tear this shirt to shreds.
The way they dressed in this realm was ludicrous. Not only that, but the cost was outrageous. He'd never get used to this realms fascination with paper currency. To own anything you needed paper. Gold was not the standard. Hook had countless gold, but very little paper. When the lad pulled this shirt for him to purchase Hook couldn't accept that a sane man would willingly pay $75 worth of paper to acquire such a flimsy rag of fabric.
He took a long breath. You're doing this for Emma. He studied his reflection and sighed.
"I don't like it."
Henry tilted his head before smiling. "I think everyone is going to like it."
His face twitched at the use of the word everyone. "You can't possibly expect me to go out in public looking like this lad. I feel ridiculous."
"You look just like the picture." Henry replied. "Just trust me."
"I'm home!"
Emma flung her keys on the countertop and shrugged off her cardigan. She immediately noticed that Hook's leather jacket was hanging on the coat-rack, and she eyed the loft to find him. They'd been spending a lot of time together recently. It was something that Emma welcomed.
"Hook!"
She glanced up the stairs, but everything was still. The hell?
"Hello, love."
She turned on the balls of her feet to greet him and practically toppled over at the sight of him.
Woah!
He'd been in Storybrooke for months and adamantly refused to wear anything but the clothing he had on the Jolly Roger. She went to open her mouth, but nothing came out. He smirked.
"Wh-? Wait. How?" Her eyelashes fluttered. "Oh my god."
"Told you." She heard Henry yell from the top of the stairs.
Emma was speechless. Her face felt like it was on fire. Hook watched as a red blush etched it way up her cheeks. She brought both her lips into her mouth. She couldn't stop staring.
"Alright there, love?" He closed some of the distance between them.
"Y-yeah." She stammered. "You look good."
He scrunched his nose before shaking his head. "I look bloody ridiculous, but if you like it-" Hook reached out and caught her hand in his. He stroked his thumb against her wrist. Emma swallowed. "Perhaps I can wear this every so often."
"Gross!" Henry called out. Both Emma and Hook laughed.
"You did this for me?"
He nodded.
She bit the bottom of her lip and tried to keep her cool. Emma wanted to smile like an idiot. "Did you pick out the clothes?" She asked running her hand against the fabric of his shirt.
"No. The lad did." Hook replied. "He was inspired by your internet search history."
Emma's jaw dropped open.
"WHAT!?"