[For a long moment he just Looks at her, like, this was a quest for pajamas? Truly, this was PJ Quest? It's a very serious moment, accompanied by his very serious expression.

Then:]

You'll want something with a high thread count and quality material. It should be comfortable, but sturdy— there's no point in sacrificing durability for style. Making a well-thought out choice now will save you from headaches— and finding a tailor— later.

[Finding a tailor, of course, because who would just replace their whole fit? That's silly.]

So, first order of business: A reliable pair of shoes. Starting from the ground up makes the most sense.