Comfort is key. Three big trends - graphic-print tees, status sneakers, and super-dark denim jeans - can go from running errands practically right into the office if mixed correctly. Printed tees may seem over - I suggest you make your own (or have a friend with an iron and some transfer paper do it for you) to keep the look sharp and unique. They still do the job of keeping chinos and a blazer casual.
Logos like Gucci and Vuitton get subdued in soft, subtle sneakers - they can add a bit of luxe-pop commercialism to an otherwise conservative outfit. Dark, dark blue and black denim jeans are all about cut. Skinny '80s pegged legs (a gender-neutral trend) and Texas-friendly Western cuts are best.
There's a lot of leeway in suits this fall - experiment with prints and don't match the coat and pants unless you have to. Both pieces are cut lean and fitted, especially through the chest and waist. Glen-plaid coats in greys and rusts are the new neutral and look great with jeans or solid-colored trousers. The hidden-contrast trend remains, with brightly colored linings under collars and cuffs you can display or not. Coordinating different stripes is also an easy way to take a chance - try an understated pinstripe trouser with a bold, colorful, wide-striped buttondown.
If you only buy one item this fall, make it a velvet jacket, an item that briefly premiered last year and is now stronger than ever. The colors are rich and flattering, the fabric is crushable and hard to damage. Worn with the previously mentioned tee and jeans, it's dressy enough for cocktails. With crisp, tailored black pants, it's the latest version of the tuxedo.
If you're the kind of guy who likes to accessorize, dig out that big, old, metallic belt buckle you won in middleschool 4H. Belt buckles are making statements this fall, and the narrow closures of past seasons just won't do. That's it. I can't wait to see you out.