I admit I don't see much fun in unusual hats in Team Fortress 2, I find them strange looking and way too expensive. I understand basic economics and something ugly as hell will be expensive if it's rare, so I just move on with my life and understand why unusual hats are so sought after, they're "unusual" items in the end.
What I do love in Team Fortress is build a perfect loadout for me to perform my daily gaming. What I bring you here right now is what I consider my main goal for my characters and what I think about some items. With time I've developed a quite different taste than what I had many played hours ago, so let's get onto it.
I always prefer weapons first, then aesthetic items. So I'll go after any aesthetic item listed here after I get all the weapons I aim for and their respective strange parts. Of course new strange parts and new weapons come in every now and then, and I might change my mind sometimes. Like the Genuine King of Scotland cape, a misc item for the Demoman, I don't have any of the primary nor secondary weapons for him (two primary? Who knows) but I still bought the cape for a key some time ago
Scout
(Main Loadout)
PRIMARY: Strange Scattergun [SP1: Heavies Killed], [SP2: Scouts Killed] [SP3: Dominations]
SECONDAY: Strange Mad Milk [SP1: Allies Extinguished]
MELEE: Strange Atomizer
HAT: El Jefe
MISC 1: Fast Learner
MISC 2: Essential Accessories
ACTION: Schadenfreunde
Commentaries: All right, first let me clarify that I once got the Schadenfreunde taunt in a drop but it was stolen when my account got robbed. My primary weapon is complete and kickin', as always, I prefer the stock primary weapon for all character, I go over the edge for the other slots but primary is always stock. The secondary weapon is complete also, the only strange part possible for the Mad Milk is exactly that one, allies extinguished.
My main doubt about this loadout is the Atomizer, I used to think it's useless but after seeing it being used efficiently I changed my mind and started using it. The triple jump it grants is not to be performed relentlessly but in key situatiuons. I used to think I wouldn't have a limit and would constantly do it granting me many unexpected deaths, that hasn't come true, but I've encountered problems. Sometimes, even while double jumping it tracks as my third jump, maybe it's my keyboard, maybe it's about timing, but I'm pretty sure that wasn't supposed to happen. And the worst of all, I jump only twice and still receive damage. Sweet.
Of one thing I'm certain, I don't want the Sandman as my primary choice for the Scout, the health loss for an already weak character is crucial, and sometimes I think it's being used as a gimmick, something flashy and fun. Of course it has its benefits and all, the stun time sure has brought me many deaths as well as many kills, but right now I don't see much utility overall and also not fun at all to use. All in all, I might get the regular stock bat if I get tired of the Atomizer and somehow be unable to control its randomness of the timing for the third jump.
For the aethetic items I picked El Jefe, one of the very few cool Scout hats (along with Ye Old Bakers Boy which I once had two, one got in a crate and one in a drop, I sold one of them when I found someone actually paying the right price for craftable hats). Getting it Genuine would be a dream, but the price is astronomical for a mere hat so I might as well get a regular one and call it a day.