Structure Leather Jacket from the late 1980s; has been through the ringer but is virtually indestructible.
Lightweight twill shirt - decent middle ground between an oxford cloth button down and a traditional dress shirt. TTS but a bit slim/short.
Vintage 505s - I'm usually a 32-33 and these are massively oversized at a 38x32 to get the pooling effect. Distressing done by hand.
Florsheim Essex Boot Great boot, though I went down 0.5 from my usual shoe size and the zipper can be a little cumbersome.
Moscot Cliptosh clip-on sunglasses - a godsend for me, a person who frequently wore oversized sunglasses only to lose them.