Nothing sets the teeth to rattling like the task of gift buying for a style zealot (except maybe an in-law’s icy glare). Rolled or cuffed? four-in-hand or windsor? Double breasted or single? Brown or black? Personal style is, well, personal; a faux pas can have lasting consequences.
That’s why we’re throwing you a life line: 36 stylish picks in 12 style mainstays that should all strike a chord with the handsome man (you, of course) in your life. From show stoppers to the little things that make a big difference, all of these wardrobe staples are accessible to just about every man’s fashion sense. Take a deep breath, struggle desperately to remember what you last saw in their closet, and read on.
Looking for more men’s gift guides? Check out all our gift guides for men this way.
1. Chukka Boots

Fun fact to calm your tense, gift-finding nerves: Chukkas are named after the two halves of a polo game. Luckily, they’re not reserved for rich Brits. These ankle-length boots are the perfect footwear solution: they work dressed up or down, and are perfect for maintaining comfort without roasting your feet in hot weather or freezing them when it’s cold. Whether they’re rugged or classic (or, very reasonably, both), they’re a fantastic footwear mainstay.
Our Suggestions: 1. Clarks Desert Boots $120 | 2. Cole Haan Lunargrand $298 | 3. Red Wing Postman Chukka $240