There are only so many layering pieces available in classic menswear. We don’t have the selection that women have, therefore we need to be a little more creative with how we put together the pieces that are available.

Henleys, in my opinion, are very underrated as layering pieces. Everybody owns a crewneck sweater, a v-neck sweater and probably a cardigan too. But don’t sleep on the henley.

The best part is, they work as well on top of a shirt as they do under.

Here, 3 layered looks featuring henleys.

Even in an uptight office, this is a casual Friday look that business folk can respect. The best part is, remove the jacket, roll the sleeves, and you just went from the office to, well, just about anywhere.

Bonus Tip: The size of the buttons affects the look of the henley. Big buttons (like the henley in look 2) are generally more casual, while shirting-size buttons look dressier and therefore work better under a suit jacket.

Bonus Tip II: When wearing it over an open shirt, unbutton the henley just enough that it’s neck opening flows with the opening of the shirt collar (in this case 2 out of the 4 buttons undone looks the most appropriate). Buttoned too high can look stuffy and unbuttoned too low looks sloppy.

Bonus Tip III: When wearing a henley over a tie, only unfastened the first two buttons to give a “v” shape at the neck rather than letting the neckhole flop open.

Bonus Tip IV: Henleys also come in short sleeve, post on this coming this summer.

Henley by Polo Ralph Lauren (size M). Blue oxford shirt by Thom Browne (size 2). Tweed suit (as featured here) by Michael Andrews Bespoke (custom made, my own design). Wingtips by Scarpe di Bianco. Vintage linen pocket square. Shades by Persol.