With a fully Polartec outer, this pullover should be a solid pickup no matter what you choose to pair it with. That said, if you're going to wear this pullover, maximize the cold-weather potential of this hyper-cozy piece. We'd consider wearing some rugged hiking boots for an fit that's flex-worthy—whether you're heading indoors or out.

Speaking of cozy, there's really no topping a smooth-as-hell satin boxing-style robe. Don't even both trying to pull this off outside of your house: either the elements or sheer embarrassment will make sure that this is a grail best suited for the four walls of your home. Keep it simple: throw on the satin robe, slide into some comfortable slippers and call it a day. Pro move: splurge on a strong pair of velvet slippers for the crib—save them as a footwear flex for the next time you need to attend a wedding.

Considering that this is dropping alongside a pair of matching sweatpants and a tee—we'd suggest trying your luck and copping the full-on sweatsuit. While keeping things "matchy-matchy" isn't always the best idea, as things get colder and nights get longer, we wouldn't blame you for keeping things uncomplicated every once in a while.

There's really no other way to put this: this piece is so gnarly it's actually incredible. All-over snakeskin anything is not for the faint of heart, and while this jacket has two counts of clout (one for Supreme and the other based off the prestige behind Levi's signature trucker jacket), it's definitely one of the louder pieces dropping this season. Don't overthink it and pair this one with a basic hoodie or tee underneath.

Love them or hate them, Mark Gonzales' seasonal designs for Supreme feature some of the most impressive, iconic and (in some cases) garish graphics in their given drop cycle. When it comes to this crewneck, let the many multicolored heads do the talking. A pair of lightwash dad jeans—chopped up, painted or plain—seem to be the perfect partner if you're bold enough to wear this sweater.