Glasses - Dean wears throwaway sunglasses he found at Dollar General, a necessary item when working outside. Cas has Oakley reading glasses, a decent pair he got at the optometrist. Money isn't really a consideration and he just tends to buy whatever is easiest. Here he picked something that felt comfortable and durable.

Wallet - Dean carries a woven wallet he's had since middle school. Bobby gifted it to him for his 13th birthday, because "every man should have a wallet". There's a zippered inside pocket and plenty of room for rewards cards and random shit he never clears out. Cas has the same Fossil leather wallet from undergrad because it's practical.

Watches - Dean wears various digital watches, yes, from Walmart. They usually last around a year before something happens. At least they're only $14.97. Cas has Cain's Omega Seamaster Ploprof, a top-of-the-line luxury diving watch Cain wore every day. Before then Cas had never really worn a watch and knows/cares very little, but it's one of the few items that is very important to him. He is diligent about getting it cleaned and serviced, and thinks it's normal for all people who wear watches to spend $600 on a 5-year service (it certainly is not normal). Cain's name is engraved on the back of the helium escape valve, and whenever he takes it off he runs his thumb over the smooth lettering.

Shoes - Dean wears whatever he can find at thrift stores, usually. He's already starting to feel his feet and knees protest when he doesn't wear something supportive, but the DC's he recently bought were basically brand new and he couldn't pass on that. Cas buys three pairs of the same walking shoes and cycles them for a couple years, and repeats.

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