Fancying up the informal is a bold move fraught with peril: truffled mac and cheese might be delicious, but truffled Todd Palin can be a bit gamey. For successfully classy casual: Distilled.
From a former 555Soul designer and a Stanford math PhD, Distilled's a "fashion line and art collective" producing upscale casual menswear using "algorithm-enhanced storyboards" that break their random ideas into images, quotes, colors, and ideally "clothes". Hoodie-wise, the Fall line includes a refined black and white herringbone design covering the chest of either a gray or pale yellow cotton zip track jacket, and the "Nob Hill" zip w/ gray terry interior and a shiny satin chest panel evoking the bling of a tuxedo, or generously Soul Glo'd man-thatch. To go even more ornately laid-back, try the "Glen Plaid" in either a thick cotton shirt jacket with double chest pockets or a stretch-cotton blazer lined with regal purple satin -- because inside, aren't we all Princes of Maine, Kings of New England?
Distilled's also hawking straight-up casual wear like plum plaid and slate wool/cotton/silk blend button downs, plus a few sales items like the Pacific Short -- a coal seersucker cargo-pocketed number so laid-back, it's the sartorial equivalent of a bitchin' goatee for your upper legs.