Putting together a grey herringbone wool suit and a navy waistcoat is a guaranteed way to infuse your styling collection with some manly elegance. Tobacco leather double monks will give a more relaxed feel to an otherwise sober look. So when summer is fading away and fall is setting in, this outfit has a good chance of becoming your go-to. Gentlemen who are curious how to dress well in your thirties, you have your answer.