Well, short answer is yes. Long answer is more iffy.
If you're asking about shoe sizes, and if they matter/make a difference to your play/striking then yes, almost always. You should always try to establish your shoes size, and never stray within a size or so of it, if possible. It's just a comfort thing and plus, you don't want the shoe to come flying off, or, conversely, squeeze the hell out of your foot, making it very painful. Different strokes for different folks, though, as I believe Ronaldo is known for wearing shoes much too small for him and, while people are saying it may do him harm in the long run... Maybe there is something to be said for it, given how good he is able to be with them. :p
Different styles... All down to comfort my man. Obviously, don't play with a wrecked pair of shoes if you can help it but, $100 or $10, it's all about how the player in them uses them.
You might also find that it is easier to juggle barefooted/ in socks/with street shoes and, while this may be true due to the wider surface, cleats/boots serve much more purposes then needing a wide instep, such as aerodynamics, spikes for digging into the ground, etc. All relative.