Even the most knowledgeable collector rarely becomes an actual craftsman, a good thing unless you want all trains to endlessly go around a circle and through a tunnel in some loser's basement. For a vintage clothing aficionado making that transition, Post O'Alls
From a Japanese-born designer who spent his life amassing 1950s Levis and blue-collar American clothing from the 20s and 30s, POs expansive line-up of workman-like duds feature design details that were once the hallmark of hardworking men, but now can be worn by men like you. Outerwear includes the button down Engineer's Jacket, with train conductor-style over-sized stitched pockets, avail in modernized denim, canvas, or twill; a hooded Sea Cruz Parka pull-over made from actual boat-sail fabric; and the flap-pocketed Cruzer Vest in pinstripe blue or tartan green and inspired by turn-of-the-century lumberjacks -- when you've got pythons that big, sleeves are always out of style. Shirts are highlighted by the Sweetlighter Supreme, a customizable button-down with high contrast stitching and an irregular hexagon insignia on the breast; an "Army" shirt made of 8oz Indigo denim; and the C-Post 4, with a left-side flapped pocket and "chin strap" inspired by 1930s naval outfits, available in waffled fabric so you can wear the very feelings you have standing outside the recruitment office
For your legs there're three varieties of boldly stitched, five-pocket jeans made from 15oz Japanese cone-mill denim, famed for it's natural fading properties, but oddly enough no overalls, perhaps because what Osh Koshers really collect are crippling insults.