The Habilitate Holiday Gift Guide 2022

Men moving wrapped packages on roller skates
Image credit: Tullio Saba / Public domain

Reader, it’s that time of year again. Hard as it may be to believe, we have been delivered once more into the holiday season and, if you’re anything like me, you might be experiencing a touch of festive jetlag. Weren’t we still line-drying laundry, watching the sunset after dinner, and occasionally leaving the house without a sweater — you know, summer stuff — just a few short weeks ago? It certainly feels like it. Mentally, I’m still soaking up vitamin D on a beach somewhere even as I type these words wearing three layers and an extra pair of socks.

Despite this seasonal affective delusion on my part, I’ve nevertheless been vaguely aware that decorations have been appearing all around my neighbourhood. Seeing those first festive lights go up is always a reminder that I better start getting my Christmas shopping list in order before it’s too late. And with Black Friday just a few days away, you are no doubt facing a similar quandary. 

That’s why I’ve assembled another holiday gift guide to offer some ideas of what you might get the menswear lover in your life (and, yes, presents addressed to yourself are most definitely included). As with last year’s list, all of the items below have been selected from articles published on the blog this year so you can read about them in more depth if you’d like. Also, all of the attendant purchase buttons are attached to affiliate links, so if you use them to buy something you help support the site at no extra cost (You can find out more via our affiliate policy).

So, with that all taken care of, it leaves me only to say: Thank you so much for reading and I hope you have the happiest of holidays. Here we go!

Carpenter Pants

A piece I wrote about wearing my Carhartt double-front work pants all throughout the pandemic was the very first article I published in January 2022 and, nearly a full year on, very little has changed as far as my trouser choices go. While I do leave the house more often than I did at the start of the year, the pants I’m typically wearing while doing so remain largely unchanged (the occasional hamper-based sabbatical on their part notwithstanding).  

What has changed, however, is that I’ve discovered all kinds of new ways to wear them — with penny loafers and white socks, with Oxford shirts and woolly crew necks, with Chelsea boots and every winter coat I’ve managed to throw at them. Heck, I’ve gotten so much use out of my carpenter pants that I am tempted to treat myself to another pair for Christmas, perhaps in white this time around to suit the snowy season we’re in.

Clarks Wallabees

The Clarks Wallabee never ceases to amaze me with its comfort, versatility, and its staggering popularity. It is, lest its ubiquity leads us to forget, kind of an odd-looking shoe. And yet people (myself included) simply cannot get enough of it. 

It isn’t much of a mystery as to why, though. Simply ask yourself, what can’t you wear with a pair of Wallabees? They go with everything from suits to shorts to sweatpants — and everything in between. They are such a go-to knock-about set of kicks that whenever I can’t decide what shoes to wear, they are the ones I’ll go with on any given day. That kind of no-brainer flexibility doesn’t come around often and definitely deserves a dedicated spot in your closet. 

Seiko 5

I have spent more than enough time on this site gushing about how much I love the Seiko 5 watch, so I won’t go on about it again…

Except to say this: The Seiko 5 is — somehow — all of the following: cheap, reliable, respectable, versatile, and extremely easy on the eye. It is, in short, the full package and it’s the only watch you’ll ever need.


…Unless, of course, you want to buy another watch, in which case I recommend you get one of these. The Casio G-SHOCK happens to be even more affordable, even more dependable, and has every bit as much of a dedicated following within the watch community.

I love mine with all my heart and despite me bumping, scratching, and generally putting it through the wringer just about every time I wear it, the fact that it just keeps on ticking along without complaint suggests to me it feels the same way. 

Hanes Beefy-T

OK, I’m about to level with you: Everyone has someone on their gift list who they don’t want to spend a lot of money on. Maybe it’s a sibling’s boyfriend who’s tagging along for the family holiday or an uncle who once gave you the same present three Christmases in a row. For that person, I recommend you get none other than the Hanes Beefy-T. It’s cheap, it’s simple, and it has just the right generic kind of appeal that works for the gift you don’t want to be giving in the first place. 

But don’t let this rather negative framing put you off, though: The Beefy-T is a stone-cold classic and also happens to be the T-shirt I wore most often this year. So, empower yourself by getting whoever you least want to spoil a multi-pack of these bad boys and, if they don’t like it, feel free to send them my way so I can set them straight.


As mentioned above, it is, as you’ve no doubt noticed, winter in the northern reaches of the globe, which means that it’s time to gear up for some truly miserable days to come. And, ideally, you’re going to want to do that in as stylish a way as possible, not least because cold-weather kit can be somewhat unsightly at the best of times. 

Luckily, though, a set of Blundstone Chelsea boots have got you covered in this respect — literally. I’ve had my pair for over a year now and, despite the absolute kicking I’ve given them through rain and snow and unforgiving outdoor terrain, they somehow still look as good as the day I got them. Frankly, I could do with a bit more wear at this point since I’d like to have something to show for all the trekking I do through inclement Scottish weather. Even so, if you’re after some sturdy, stylish shoes to get you through the dark days ahead, look no further than a set of Blunnies. 

Penny Loafers

If, however, you’re after something a tad dressier — something that shows a bit of shine, a flash of sock, and a sense of fun — go for some penny loafers instead. These are your one-stop loafer: They can be fancy or casual, demure or eye-catching, a go-to shoe or something you save for more special occasions. 

After all, the holidays are for loafing, so why not do it in a pair of pennies?

Aviator Sunglasses

As I type these words — I kid you not — Top Gun: Maverick is still playing at my neighbourhood multiplex. You know, that movie that first came out six months ago? No wonder I barely know what season it is. 

What this suggests, beyond all shadow of a doubt, is that this is Top Gun’s world and we’re just living in it. Which is why you’re probably going to want to get yourself and your nearest and dearest a pair of aviator sunglasses so that when Tom Cruise inevitably becomes our jet-flying overlord, he’ll know you’re on the up-and-up. 

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