@highsnobiety: @Jay Guapõ is making sure the whole fam is @timberland-maxxing this holiday season. Hitting up NYC’s forefather of fly @Bloody Osiris on the Timbs Tips hotline, the two style savants break down which pairs are approved stocking stuffers (and yes, a Timberland can fit in a stock if you believe hard enough). From the staple Beef and Broccoli Field Boot to the elevated Stone Street silhouette, Jay Guapo is making sure everyone is certified when stepping out of the crib this season. Hit the link in bio for advice on any style woes and footwear frustrations. We got you. #jayguapo #bloodyosiris #timb #timberland

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Tuesday 20 October 2026 21:10:40 GMT