A crew-neck sweater and navy vertical striped chinos are absolute menswear staples if you're crafting an off-duty closet that matches up to the highest style standards. A pair of dark brown casual boots will bring a smarter twist to this outfit. While it can be a bit of a juggling act to look stylish in extra cold, it's combos like this that prove it's actually possible. And if we're talking casual outfit ideas for over-40 gentlemen, this getup looks cool on almost any gent.