I've def become more successful gifting with my hubby now that I have rule against the"wishful thinking" gift - whereby I buy something that I think is awesome but my husband has exactly 0.01% chance of using, much less, liking it (leather coasters, e.g.). Here's a pretty good collection of tried and true options that your guy is sure to love.
1. Sid Mashburn Field Jacket. Beyond being exceedingly hip (literally every dude in Europe has one of these), this is the most practical gift you can give your guy. Worn alone or over a blazer for extra warmth and for an extra dash of super coolness. A low key substitute for the ubiquitous puffer jacket.
2. 128-oz Pressurized Growler. For the habitual tail-gater on your list. This baby will keep your craft beer cold for days. #legit
3. Essential Tailored Vest by Barbour. A more updated version of the old standby. This one is warm and light without all the bulk.
4. Trailblazer LED Flashlight. Staggeringly bright, lasts forever, charges with an USB cable, and with a 3-point articulating head, every guy on your list will want one of these.
5. 48-hour Duffel by T. Anthony. For when you aren't travelling by plane. This duffel is ingeniuous - it's eesentially a hanging bag that zips up into a duffel. Your guy won't call attention to himself when he checks in with this bag, (which he will like) but it will look nice and refined just the same (which you will like).
6. No. 7 Stainless Steel Pocket Knife by Opinel. At $15, this handy and handsome knife is the perfect stocking stuffer.
7. Total Wit Readers in Tokyo Tortoise by Eyebobs. Because who among us can resist Atticus Finch???
8. Ceramic Flask by Misc. Goods Co. The only flask any self-respecting, bearded, bow-tie wearing, Billy Reid Shindig-going millenial would ever carry. And, also, it IS pretty cool.
9. Cantwell Ice Bucket by Ralph Lauren. Up his bar game like a boss.
10. Suede Drivers by Tods. Timeless, effortless, and comfortable. Word.
11. Sphere Ice Molds. The perfect stocking stuffer for the whiskey drinker in your life.
12. S Is For Southern by the Editors of Garden & Gun. An illustrated encyclopedia of age-old traditions of the South, like why it's always Kentucky whiskey and not ever bourbon.