The Habilitate Holiday Gift Guide 2021 — Part 1

Woman with a megaphone pointing
Image credit: Tullio Saba / Public domain

Happy holidays, dear reader! As I write this, I’m sitting by a crackling woodfire, wrapped up in a festive cardigan, and pausing between clauses to knock back some mulled wine-flavoured tea (once 5 p.m. hits, I fully intend to take the ‘tea’ out of that particular equation). It’s all rather cosy and it can really only mean one thing. That’s right, we’ve reached the final week of November and are thus plunging headlong into the festive season. 

This time of year can be a challenge at times, but the early months of winter are equally filled with silver linings and happy consolations. Sure, colder days and longer nights may have arrived, but so have coat weather and Christmas lights. No question, it can be tough to be alone or with family over the holidays, but at least there’s the promise of eating way too much trifle and passing out while watching Home Alone (Just me, maybe?)

Another perk of the season can be the chance to get yourself or a loved one a token of appreciation or two, which is why I’ve assembled the first annual Habilitate Holiday Gift Guide. Here’s how it works: I’ve put together a list of gift ideas, each of which is based on a topic covered on the blog this year. In every instance, I’ve included a few notes about the item, a link to the original article, as well as a product link should you wish to get anything (These are all Amazon affiliate links, so if you buy something using it you help support the site at no extra cost to yourself. You can find more info over at our affiliate policy). 

I had a great time putting this list together. So much so, in fact, that in no time at all it proved rather lengthy, which is why I’ve gone ahead and split it up into two parts. If you want to check out Part 2, tune in again later this week on Wednesday for the second instalment. But so, without further ado, go ahead and scroll on down for some gift-buying inspiration for the menswear lover in your life — and, yes, it’s entirely acceptable if that person is you. 

Man walking wearing a red bandana face covering


Over the last two years, there has been a great deal of speculation in the clothing world about the ways in which the pandemic has altered the way we dress. In my own case, the single biggest change has been this: Before the pandemic, I didn’t own a single bandana; now, I almost certainly have one too many. I first started buying them back when face masks were still hard to come by, but when scientific research into the efficacy of different face coverings showed that kerchiefs weren’t an especially viable option, I soon put them toward purely aesthetic purposes instead.

I continue to acquire them at an alarming rate and now rarely leave the house without one. When I’m not using a bandana as a means of adding interest to a given ensemble, I simply stuff one in a pocket in case something needs mopping up or similar. I’ll usually pair them with crew necks (whether on shirts, sweaters, or sweatshirts), especially as a means of preventing any neck chafing and for keeping dirt off a jacket collar. Increasingly, I also like the look of simply having one draped inside of an open shirt collar or wrapped within the neck of a mock- or turtleneck jumper.

Back view of a person in a bucket hat

Bucket Hats

It took me a minute to get the bucket hat craze. Since I’m neither a zoomer nor a boomer, I fell somewhere outside of the typical Venn diagram of bucket hat wearers. But once I was able to cast aside the childhood associations of my dad mowing the lawn in a boonie and short shorts, I embraced them with open arms and haven’t looked back since.

If you too have any similar reservations, fear not, for I’ve found there is nary a wardrobe that can’t accommodate a bucket hat or two. If you’re not into the pre-Vogue cover Billie Eilish vibe and instead favour a more conservative, traditional aesthetic, just look to folks like Bruce Boyer, Ethan Wong, or Dick Carroll for inspiration. 

Once I came around, I wore mine all the time during the warmer months and have been surprised to find them equally useful in colder, rainier weather, especially when paired with the turned-up collar of a denim jacket, a Barbour, or a sport coat. What’s more, when the skies clear up or you step inside somewhere, you can go ahead and stuff your hat right into your pocket, which is liberating when you’re used to wearing decidedly unfoldable baseball caps as I am. 

Flat-lay of a pair of white jeans

White Jeans

White jeans represent perhaps the biggest style revelation for me of the last few years. For a long time, they weren’t on my radar as an even halfway viable option. ‘How could anyone,’ I thought, ‘who isn’t an ’80s drug lord or the proprietor of an indecorous discotheque put on such a garment?’ Then, of course, I started seeing them on exceptionally well-dressed men — people like Alessandro Squarzi, Simon Crompton, and Aleksandar Cvetkovic — and at some stage it all clicked. Not only are white jeans stylish; they are, in point of fact, essential.

Once you shrug off the party boy associations and the constant fear of getting them dirty, white or ecru denim rapidly ascends from outré trouser niche to wardrobe MVP. You’ll find that you can wear them with anything and to anything (or just about), and you can do so at any time of year, as long as you keep an eye on the weather forecast to avoid heavy rain and mud. But, if you do get dirt on them (which you definitely will) unlike with those grimy raw denims stinking up your freezer, you can just pop them in the wash and you’re good to go again. They really only get better with some miles on the clock. So don’t fear the dirt, embrace the flash, and wear the hell out of some white jeans — you’ll never look back.

Colourful New Balance sneaker

New Balance

If anyone you know is in the market for a pair of sneakers (yourself included), you can basically never go wrong with a pair of New Balances. They are, as one of their ad campaigns once memorably put it, ‘worn by supermodels in London and dads in Ohio’ — them, and everyone else in between. With an impressive pedigree, unbeatable comfort, and a wide range of styles, colourways, and collaborations to choose from, just about anyone is bound to find a pair of New Balances they’ll love. Which is all the more impressive given how uncool they once seemed and how inscrutable their product names can be.

Despite having at this point nearly worn through the tread of my go-to pair, they’re still the comfiest, grooviest trainers I own. I’m always on the lookout for a new set, though, and very nearly stopped a man on the street in my neighbourhood the other day just to pick his brain about his New Balance kicks. If I spot him wearing them again, I’m definitely going to do it too. The true spirit of the holidays is, lest we forget, all about togetherness and talking about trainers.

Be sure to come back again on Wednesday for Part 2.

* This post may contain affiliate links. If you buy something using them, we get a small percentage of the sale at no cost to you. More info at our affiliate policy.