When is something handmade cheap, and when is it chic and dapper?

[Mod says] The comments referring to the errors in the OP prior to editing have been removed.

With that said, lets get to the real answers. :-)

Others may insist on a known designer to consider something chic, as far as I’m concerned, beyond the fashion there is: craftsmanship.
If your aunt can put something together with clever and sturdy stitches then there is much to be proud of.

The movie “Pretty in Pink” has a fun example of home-made chic fashion that was successful for the maker.

Some folks will go really far to attract attention with the uniqueness of the design – that is where, in my opinion, you can run into trouble with something that definitely catches the eye but beyond that doesn’t actually look attractive &/or is distracting from the beauty of the wearer.
Different-to-be-different is fun and is a way to express yourself. But it doesn’t rock my boat as much as something that advances the art a bit.

It all depends on the quality of the workmanship. A skilled milliner/dressmaker/seamstress can hand make something exquisite. That’s why a handmade object from a fine store (think Hermes, not D&G or Victoria Secret) is valued, they use the best craftspeople around.