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Given how strange their lives already are on a daily basis, it's no big surprise that the four of them adapt to COVID-19 with minimal fuss. They've always spent the majority of their time locked up in the Bunker, closed up together in the car, or otherwise separate from society. It's a hunter's lot: working the case in the shadows while normal people get to go on with their normal lives. Honestly, they were bubbled before bubbles were cool.
So, social distancing? Team Free Will 2.0 says "no problemo".
The masks are a bit more of an adjustment. Obviously they need to cover up before talking to witnesses or meeting with law enforcement (or getting groceries). It's less clear whether they need to stay masked during the more nighttime-oriented parts of the job. Can they pick up the 'rona in a vamp's nest? Or during a salt and burn? Unsurprisingly, the lore is silent on the subject, although Garth swears up and down he once caught a nasty cold from a wendigo he was tracking. They decide to err on the side of caution: Any time they're out of the Bunker and out of Baby, they're masked up.
They bought some plain ones online that they use when they're on the job -- very boring black cotton with a government-issue look like a good FBI agent would have. The rest of the time? They're in any of the dozens of colorful, garishly-patterned numbers that Cas has been sewing in his spare time. Dean's current favorite is, of course, patterned with little slices of cherry pie. Jack prefers any of a set of six that Cas whipped up from a pack of fabric in assorted animal prints. Sam says he grabs whatever comes to his hand first, but Dean's noticed that the masks made from their old flannel shirts seem to come to his hand every single time he grabs. Cas's masks are always some shade of blue, after Dean told him once (okay, maybe more than once) that blue makes his eyes pop.
Dean installed a couple tie racks by the door where they all hang, which has helped a lot with remembering to grab a mask before heading out to pick up beer or whatever. Jack was still forgetting his a lot, though, until Cas found an idea on a "raising your preschooler" website that suggested making up a song about getting ready to go out. Now the two of them sing Jack's "let's get ready" song whenever they need to go somewhere, and the simple rhymes prompt him to remember his mask, his phone, his jacket, and how much his whole family loves him.