Brooks Brothers – that stalwart of conservative dressing – has a lot to offer in the restrained button-down department. The quality of the shirts is great and, unlike most of the brands on this list, they have much, much more to offer in terms of specific sizes, as they take both neck and sleeve measurements into account. This is great for guys who are unusually tall, short, or round, but all guys can find something to love here. Brooks Brothers is at its best when it gets a little wild, like its Framed Gingham, Large Plaid and Bold Check dress shirts. We also wouldn't blame you for getting a dress shirt in classic white. And always, always go for shirts with their Ainsley Spread Collar – otherwise you'll look like an old fogey. [$92; brooksbrothers.com]
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