As we hit the winter months, the standard tee is not enough to keep us warm. The long sleeve T-shirt is coming into the wardrobe rotation, and with that, usually comes the decision of whether to put a button down shirt over it to look nice or to just sport the old long sleeve tee itself, a look that should be most likely be reserved for the gym. This is where the Henley comes into play. The semi-button, no-collar combo is the hybrid child of a polo and tee shirt.  It perfectly teeters on the line between upscale and casual, and can be paired with a sport coat or worn by itself with almost any pair of casual pants. The Henley is a great choice for travel, or for long-haul days when you’re not sure what the later hours may bring. The Henley is versatile and functional for most daytime activities and conditions, whether it’s a coffee date on a snowy afternoon, or an outdoor excursion with your mates on a warmer winter day.

They have recently cycled back into mainstream fashion from the late 80’s, which means your father may have some vintage henleys hanging out in his closet that would be a great find and conversation piece. So while you are with family around the holidays, try asking the old man for a peek at his closet, provided you’re the size he used to be.

If you strike out with the free vintage option, there are plenty of good companies making solid Henleys. J. Crew, Banana Republic, The Gap, and even PacSun are stocking some great choices at pretty reasonable prices. If you’re undecided on color, we suggest dark blue, beige, maroon, or forrest green for this season.

Already rocking the henley and have some killer wardrobe combos? Post a pic in the comments and share some pairing ideas.