Remember to add articles (a/an/the) to your sentences before nouns (boy/car/cat/hose). For example, instead of saying "What does boy look like?" you should say: What does the boy look like?
Also before with dress and wear.
Dress mean put on one's clothes.
"Graham showered and dressed quickly"
Wear means have (something) on one's body as clothing, decoration, or protection.
"he was wearing a dark suit"
In your first sentence the word dress is appropriate, if you rather say: How does the boy dress?
For your second sentence you should rather say: What is the boy wearing now?
I hope that this is helpful. Please feel free to ask if you have any questions :)