nopony said:
Just let everypony (and dragon) choose what their fashion sense is telling them. Then go to the hostel and check if they have any work you can do in exchange for spending the night there.

You get 4 Black Snow Boots, Charcoal Coat, Charcoal Ushanka, and Tan Muffler! You are not wearing saddlebags, so you equip them instead.

With your party now properly dressed to withstand the local wintry climate, you thank Platinum Twine for doing business with you, and exit the tailor's shop.

Once back outside, you can already feel the difference; the wind that had you shivering before is now but a cool breeze on your cheeks. Satisfied with your new garments, you take a look at the time. A nearby clock tower indicates a quarter past six.

You recall being told that the hostel might offer some job opportunities, so you suggest heading there next for a chance at a hot meal and a warm bed. Your friends agree with that plan, and you begin to follow the road south to the hostel.

On the way there, you notice dozens of ponies pouring in through the city gates. Within minutes, the streets bustle with activity, and while your group gets a few lingering looks, your best smile usually sends passersby on their way.

Moonflower: "I wonder what's so bad out there that everypony's gotta stay inside the city walls at night."

Smoke: "Heh. Nothing I can't handle, that's for sure."

When you enter the hostel, you find that you are among the first to make it in, though a line quickly forms behind you. As you wait for your turn, you overhear some conversations.

Old stallion: "I heard it's probably going to rain tomorrow. Eighty percent chance!"

Young mare: "Great. What's the other twenty percent, hail or snow?"

You soon reach the front desk, behind which sits a mare with a slightly disheveled mane. She hurriedly scribbles something down before looking up to greet you — and catching sight of the tall, black-scaled creature behind you.

Receptionist: "Weeehhh-lcome…?! Ahem. Welcome!"

You greet the receptionist in turn, and tell her that you and your friends are travellers looking for work in exchange for dinner and an overnight stay. As you speak to the mare, however, you get the impression that she is distracted by the rapidly growing crowd in the lobby.

Receptionist: "Um, right. Dinner and overnight stay, was it? Rooms are still being prepared, but they should become available any minute now… wait, did you say you were looking for work?"

You nod, and reaffirm that you are. Suddenly, you have her full attention.

Receptionist: "Oh! Thank goodness. Honestly, we could really use the help; half of our staff is on leave today, so we're short a couple chambermaids, a laundry operator, a porter, and a cook.

If you could fill any of these roles until midnight, we'd gladly let you have a room in the morning. Dinner and breakfast included!"

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