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Brian’s “Modern Man/Cool Dad” Gift Guide (Tested And VERY Approved)

*Disclaimer! Brian Henderson took NO part in creating the title of his blog post:)

When I was in third grade, all I wanted for Christmas was a plastic Rambo machine gun with a tripod mount that had a hella cool grenade launcher attached below. Can’t really believe that they made kids’ toys based on an R-rated movie like Rambo III, but hey, it was the 80s. I wasn’t much of a gun guy, even back then, but something about Sly Stalone’s lubed-up biceps cradling that thing in the commercial really made me want one. So my parents (or maybe Santa) came through, and on Xmas morning, I found that hella cool toy gun waiting for me beneath the tree. I’m told I was elated. I’m told I couldn’t wait to play with it. But I have no recollection of that morning, because apparently, before I had the chance to play with any of my toys, I went out to the garage to grab something, orange juice, maybe? And when I came back inside, a full twenty minutes later, I was aghast to find that Christmas had already happened. I saw all the toys and wrapping paper strewn about and immediately went into a panic. “Was it Christmas already?” I frantically asked over and over again, my eyes in a dizzy glaze. My parents were understandably freaked out about my state and rushed me to the ER, where it was determined that I had somehow bumped my head while out in the garage and sustained a pretty bad concussion. We think that maybe our large Labrador had knocked me down to the concrete floor. But the result was a kid who couldn’t remember Christmas. All the joy and excitement that I’d experienced earlier that morning had been forever lost down a black drain of amnesia. Sad, right? Well, the moral of the story is to make sure you take videos of your kids opening presents so when they get concussions they can relive Christmas morning. And to give presents that people will really remember. I’ve composed this list of memorable gifts, which will hopefully help you with the man in your life. Personally, I’m going to add a football helmet to the top of my list and wear it all morning long. Okay, here we go.

Trembly Jacket

Living in Oregon, layers are extremely important, as is a good weatherproof jacket. This one has become my go-to outer layer on those early fall days when the weather is starting to turn. It’s light enough to layer beneath but warm enough to throw over a t-shirt if that’s all you need. Big fan.

Skyridge Boot

Speaking of Oregon, it’s constantly raining up here in the winter and demands some good waterproof shoes. It’s hard to find ones that both look good and get the job done, but these Danner boots pull it off. I really like the retro hiking boot vibe. Plus they’re very warm and comfy.

10-Year Full Zip Hoodie

I spend most days typing away on a laptop and usually go between being too hot and too cold, so I’m a fan of zip-up hoodies. This one lives up to the name, it’s rugged but soft and very well-made. I think it could go 10 years, unlike some cheaper hoodies I’ve had in the past. Well worth the money.

Legend™ Sweater Shirt

I’ve always had fantasies of being a lumberjack, and this shirt helps me feel like I just might be one. The blue and white plaid is so good, and the fabric is so soft, it’s a contender for the “I’d wear this every day” award.

Seaboard Soft-Knit Shirt

J. Crew is still one of the best. Always well-made and comfy, this shirt can last years and never go out of style. Excellent winter shirt.

Rugged Merino Wool-Blend Cardigan Sweater

Speaking of J. Crew, I got this cardigan last fall and I still wear it on a weekly basis. It’s so cozy, it’s like wearing a blanket. Sometimes I’ll just wear sweats and slippers and toss this on with my morning coffee and I feel like a super dashing professor of literature or something. And when I wear it out, I def get jealous glances from other dudes like, “Why can’t I pull off a chunky cardigan?” Well, you can! Just put it on and you pull it off!

Manawan™ II Slipper

Slippers have always bugged me, they usually get all floppy and flimsy after one month of use, but not these bad boys, these ones are keeping my footsies toasty all winter long. Sorel is known for making long-lasting shoes and their slipper game is pretty toight.

Ray Jersey Hooded Robe

Not a robe guy. Never have been. Until I felt the sweatshirt vibe of this guy. Now I’m a robe guy.

Men’s Ankle & Calf Sock Gift Box 12-Pack

Socks are always a good gift. Well, not always. If they’re bad socks, it’s a bad gift. But I love Bombas and would happily receive many more pairs if Emily wanted to stock up my sock drawer.

Air Jordan 1 Low SE

I mean, just look at these. Classic, throw-back Jordans that aren’t too flashy for a lame dad like me. I get compliments on these from other dads all the freaking time.

Customized Hat

I’ve made too many hats using this customizable hat company, it’s a problem. I made some with our dogs’ names on them, I made some with the kids’ elementary school, and even the local high school’s mascot for when we go to their games. I’m a fan of the “dad hat” version, it fits well and is super well made. I would love a custom-made hat for Xmas, you can write whatever you want on it, like “Superdad” or ‘My Wife Made Me a Hat” or “I Have Flatulence”… anything!

Frontside 5-Pocket Pants

Quality pants for everyday use. And they have really good colors. I’ve been steering away from jeans lately and enjoying some classic chinos. These are some of the best.


This color of beanie is the best ever. Change my mind.

YETI Cooler

We’ve started to do more camping up here in the PNW, and have found that normal coolers just don’t cut it. You need the real deal to keep all those, ahem, sodas ice cold for the whole trip. YETI is pretty tough to beat in that department.

Spellbinder Parka Jacket | Caliber Parka

While camping, you’re going to want a warm jacket, and these two have served me well. First, the more lightweight Spellbinder parka from Howler Bros, which is THE coolest-looking parka ever. I’ve got the blue one and get asked where I got it all the time. And when it’s super cold out, I toss on my Caliber Parka from Flint and Tinder and I’m cozy and warm all day long. This is my go-to parka all winter long, it’s rugged and tough but has some stylish details that set it apart.

Allegheny Fleece Overshirt

Winter is all about cozying up next to a fire, and this fleece overshirt is just begging to be worn beside some crackling logs. The pattern is cool without being too flashy and the brand has done well by me in the past.

Pacific Crest Weekender

Everyone loves upgrading their travel stuff, and this set is awesome. It’s masculine without losing style and the matching dopp kit makes any guy look like he’s got his stuff together.

Greenpoint Canvas BBQ Apron & Grilling Utensil Set

This one is a no-brainer. I love to grill, I love looking cool, and I hate when burger grease gets on my pants this offers it all. It’s a nice apron, with tons of nice little details, and it comes with some BBQ tools? Come on. It’s a home run.

Ooni Koda 12 Outdoor Pizza Oven

Staying on the cooking train, we recently got this Ooni pizza oven and had a blast making pizzas for a bunch of families. It’s simple to use, just hook it up to your BBQ propane, then make your dream pizza. It’s also a great family activity – keeps the kids busy and interested in cooking. The pies cook in under two minutes, which so cool, and they taste like they came from a fancy restaurant. It’s a big hit at our house.

BOGS Men’s Ultra High Tall Insulated Waterproof Work Rain Boot

This one’s for anyone who’s got pigs or alpacas, or just for some good old-fashioned yard work. I throw these Bogs on, sometimes even without socks, and they keep my feet warm and dry all winter long. They’re way more comfortable than I anticipated, which has made doing my chores much more pleasant – I’m stepping in pig poop all day with these things!

A Mustache, A Pipe & Pretentious Behavior Candle

As some of you know, I’m in the middle of getting my masters in creative writing, working on a novel that is (hopefully) approaching the finish line. I like to keep a candle burning at my desk when I’m writing, it makes me feel all artsy and pretentious, which is why I love this candle and its sense of humor. I’d love this in my stocking.

Men’s Essential Pocket Tee

I think I’ve put these pocket tees in every gift guide I’ve ever written, but they’re still my favorite. They’re tight in the right places, loose in the others, and are super-duper soft. They’re literally all I wear, and they’ve expanded the colors so you can get one for every day of the week!

Red Wing Heritage Iron Ranger 6in Boot | The Original Stretchlace

This is a big investment for shoes, but well worth it I think. These boots are classics and they will last a lifetime. I’ve worn mine in the rain, the snow, the bright sun, and they look as good as the first day I put them on. I love these boots. And here’s a little hack if you get the boots – put in pre-tied stretchy laces so you can just throw them on without bending over to tie! It’s the best!

Portable Pickleball Net System

The Hendersons have officially jumped on the pickleball bandwagon. You may hate the sound of the balls being hit, but you’ll love how easy it is to learn and how quickly kids can pick it up. This is the net we have and it’s great, you can set it up in minutes on your driveway and get playing!

Four Paddle Pickleball Set

But you can’t play with ugly racquets, so get some good-looking ones here. I especially like the 70’s retro-inspired themes.

Hope some of these help and happy gift shopping!

Opening Image Credits: Photography by Sara Ligorria Tramp

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6 months ago

I can attest to how wonderful Bogs are for outdoor work. I wear them to garden all year, so easy to slip on and off and they keep my feet clean and dry. So comfortable too. Erin Benzakein who runs Floret recommended them.

Crissy Perham
6 months ago

Listen…I’m here everyday for the ladies and all the work you put into this blog but…I smile the whole time reading a post by Brian. Thanks for a great list and some chuckles this AM. Much appreciated on both accounts! And good luck on your Masters and that novel!!

6 months ago

This is such a legit list. My 31-year-old almost-a-dad husband (our first is due right after Christmas!) would love all of these. 2 things I’d give a +1 to:

  1. Bombas socks-my husband is OBSESSED with them and would be so happy to get them (even though I personally find that to be the most boring gift in the world.) They’re sort of pricy to buy regularly so he looks forward to getting them for Christmas. His brother loves them too!
  2. Candles seems like a kind of weird dude gift but my husband is really into them, especially this one right now: CapriBlue Apple Cider Social. He has a tiny one on his desk all day and moves it around the house when he’s somewhere else 🙂
Leah 🇦🇺
6 months ago

Thanks! Just put the shoelaces on the list for the family stockings.
Question: how do you store all those hats?

6 months ago

just added stretchy shoelaces for my husband who can’t keep his laces tied.

6 months ago
Reply to  Patricia

Laughed out loud when I came across this ☺️

6 months ago

Good list, and helpful. I’ve got my eye on the pickleball net. Fun fact, you can put 4 pickleball courts on on regular sized tennis court.

6 months ago

I always appreciate a Brian Henderson post. This is so helpful for my Christmas shopping needs.

6 months ago

Thank you for this, Brian. Your posts are always a delight and your gift guides save my bacon regarding the men in my life.

6 months ago

Lots of good ideas here for my husband – but what I really want to get him is an alpaca!

6 months ago

I enjoyed your post, Brian.
Thank you and good luck with the novel. I am intrigued and fun of admiration.

6 months ago

Thank you so much for these recommendations! I’ve been struggling with what to get the men in my life and love so many of these, especially the Legend Sweater shirt and 10-year hoodie. I, too, always greatly enjoy your posts and wish you so much luck and inspiration as you complete your novel and Masters!

6 months ago

I think you suggested those stretchy laces last year, and they’re so great! I got them for my teenager who was just yanking off his still-tied shoes all the time and then trying to cram his foot back into them, to avoid ever having to un-/re-tie his shoes. Now he doesn’t have to! So thanks 🙂
Also, pro tip: as a former pig owner, we used to pull Dickie’s on over our regular clothes, then the knee-high rubber boots, before we went out. That way when you’re done you can hose off the boots, pull off the Dickie, and you’re still clean and (mostly) odor-free!