Winter’s Clothes
First, two notes:

One:  I think that Winter engages in a combination of actually knowing how to tailor his own clothing and using strand-working to make everything lie Just So, because I do not picture any of the RoundTree siblings particularly rich (Summer might be, eventually, but who knows?) but damn, the man dresses like a million bucks.

Two: I started a Pinterest page for these RoundTree-Family clothing images and anything else that strikes me as being Very Stranded. 

Now on to Winter.  Winter likes to dress very nicely, very tidily, and very professionally.  His impeccable dress and his neatness have led some of his co-workers to speculate that he’s suffering from some sort of Obsessive-Compulsive disorder, but Winter is no more disordered by being centered on Order than his sister Spring is disordered by being centered on Chaos:  That is, they like chocolate, but they can stop eating it without an effort. 

Winter, Every Day, above and below.
(Source 1 ; Source 2

Although Winter probably indulges in ties with lovely, complex knots, as so:


Winter when on a casual day, above and below (I imagine the denim is when around his family, tbh).

(Source 1; Source 2)

And there you have it!  Winter, his style from day to day. 

He has, by the way, perfectly-white hair in a very tidy ponytail that goes halfway down his back, and has had white hair since his late teens.