Let's be honest. The Chef's Hat and Cylinder Hat are silly items for a game like H&H. The idea is a good one though. Clothes make the man, after all. I want to see people wearing all kinds of things. So let's take the suck out of these items.
Outfits.
It's very simple. You wear an outfit, you get skill bonuses or some kind of favor from the Random Number Gods. Maybe even added functionality., One piece doesn't provide any real bonus, these are clothes tailored to a specific job and just wearing the boots won't help you. The outfits need to be somewhat appropriate for the setting. A hunting outfit might lower the chances of an animal running from you. Things like that. I wouldn't exclude a single item that isn't part of a set from providing bonuses, just make the outfits better. To start off, I suggest:
Ceremonial outfit. Pants, shirt, and cloak made of animal hides and various plant life. You know, a dried hide combined with taproots and maybe some leaves. Gets you in the mood for ancestral worship, providing some extra numens. Not that useful now but could be later, if worship is expanded. If the ancestors smile on you, they might even provide a special bonus for wearing the getup.
A fishing outfit. Waders, a straw hat to keep the sun out of your eyes, and a fishing pole. The waders would take up both shirt and pants slots. I suggest boiling the waders in wax as a method of waterproofing. You find more worms when digging and your chances of losing hooks/line/etc are lowered.
Smithy's outfit. A heavy leather apron, craftsman's belt, and bandana. Smithing is, well, hot work. The apron saves you time otherwise spent hopping around screaming "Ow!" when you get slag on your regular clothes. The belt holds your tools at the ready, allowing you to work more efficiently. The bandana? It looks cool, keeps perspiration out of your eyes, and lets you wipe sweat off your neck in a very manly way. Improves the quality of processed ores and goods requiring an anvil and/or reduces the time required for these tasks.
The Catch.
You can't wear one outfit with another. You also can't wear them with armor. The armor would interfere with your mojo. Sure, your spiffy fishing outfit is awesome but you might be surprised by a band of roving rovers, intent on poking you with holes. Will you take that risk?
Okay, it's not a big risk in H&H right now. Someday, when combat is balanced and there as lots of people playing, it might actually be a risk. At least you now you can put those three wardrobes to use. If nothing else, these outfits will make for better atmosphere in the village. Bob will really look the part of village smith now. If you have outfit ideas or better benefits, fire away. Or just call my idea stupid. Whatever.