21 Christmas Gift Ideas For The Smooth Operator Who Likes To Look Sharp
— 5 December 2022

21 Christmas Gift Ideas For The Smooth Operator Who Likes To Look Sharp

— 5 December 2022
Randy Lai
Randy Lai

He goes by many names: ‘dandy’, ‘aesthete’, ‘fashionisto’, ‘drip enthusiast’ – the list goes on. Regardless of whatever precise term of endearment you’d use to describe him, nearly every posse includes that one guy who is seriously passionate about his menswear. And let’s be honest: he’d probably be the most annoying person in the room, if not for the fact that that same invigorating knack he brings to copping fashion permeates literally every other aspect of his existence.

It follows then that it can be a bit of a sticky wicket buying for someone just so damned discerning – ditto if the man in question is your spouse, son, or senior director. Fortunately, as always, we’ve got you covered on that front: having assembled a best-in-class Christmas wishlist that straddles the divide between wardrobe essentials and balmy statement pieces heaving with ‘big fit energy’.

Blundstone #063 Men’s Dress Chelsea Boots

Kicking off feet first, how about a recommendation that virtually every man and his dog can get behind – handcrafted Chelsea boots by Tassie bootmaker Blundstone? For the gent who prefers to tread the road less travelled, the brand’s #063 Men’s Dress ($230) full grain leather boots in black sport a double-stitched sole and unique shock absorption system. We’re willing to bet that Mr. Contrarian will love the chunky sole and subtly rounded toe box: details that make this the ultimate bookend to any outfit with a ‘tactical’ aesthetic – and a more imaginative choice than the ubiquitous fashion sneaker. They’re soft and supple, but also water-resistant, durable, and built to last.

Putting your best foot forward is always sound practical advice, yet a high-quality shoe cries out for menswear that is similarly comfortable, stylish and adept at cruising through myriad settings Christmas is sure to throw at you. Ascot Chang’s ‘Azure’ Shirt ($307) in an airy cotton/linen mix is just the ticket: ideal for the man who rates dressing well, without going overboard. Topped with the brand’s patented ‘Ascot collar’, this is a bit of kit that excels far beyond the confines of the office – designed to be worn sans tie, with or without a blazer. Who doesn’t love options?

Speaking of options, not every style-conscious operator will want to settle for Chelsea boots or classic shirting. That said, you can always hack the task of gifting for the man whose tastes skew esoteric by doubling down on premium accessories. Consider splurging on handmade aviators à la Cutler & Gross’s big brawny 0822V2 ($611) or an Emporio Armani Card Case ($380) crafted in minimalist calfskin – both versatile options which cater to a wide range of tastes, and proof positive that good things certainly do come in small packages.

Azure Shirt in Cotton/Linen by Ascot Chang

Turning our attention now to the man whose penchant for smart looks is matched only by the time he spends on the road, Drake’s latest iteration of the Jungle Jacket ($930) is outerwear that combines form with glorious, glorious function. Despite its nominal foundation in the classic ‘Nam era jackets of yore, this navy version (cut in a dense Japanese herringbone that’s wearable most months in the year) is built with a relaxed, contemporary fit: layering you can throw on and forget about, up until the point when you’re reaching for cards, keys, eyewear – or even a cheeky flask of Bourbon. 

Jungle Jacket in Herringbone Cotton by Drake’s

Given that Christmas is a never-ending occurrence, you don’t necessarily even need to reinvent the wheel when deciding on what gifts will steal the show. A good rule of thumb? Buying the best possible version of something you know the men in your life already wear and absolutely dig.

For the amateur athlete – who come Saturday morning prefers digging his heels in on the hard court – the Lacoste L.12.12 polo ($120) is sure to appeal. Likewise, if he’s partial to spending weekends in the garage or astride his Harley, consider investing in a pair of RRL Five-Pocket East-West Jeans ($619) – American-made and designed by the inimitable Ralph Lauren. And lest we forget: no matter whether the man you’re buying for surfs the cutting edge of trends or is an unabashed classicist, we could all use a bit more support where it counts – explaining why jocks like GUESS’s Boxer Trunk 3-Pack Set ($59.95) are always a solid bet.

Fortunately, it’s not all Lacoste polos and jungle jackets in this BH Christmas Gift Guide. If you have a more gentlemanly persona in mind, it’s seldom a bad option to consider gifts that exist beyond the sticky clutches of fashion.

Sportcoats cut to a softly tailored proportion in tonal blends of silk, cotton, and linen – such as Suitsupply’s Grey Houndstooth ‘Havana’ ($699) – are always an effective way to convey polish without surrendering to the vagaries of fashion. But for the bloke who’s partial to a good low-key flex, Gucci – inexplicably enough – can certainly help with that. The Italian fashion titan’s ‘Diana’ Duffle ($7,425) sneaks in a handful of choice design elements – the Bamboo collection-inspired top handle being the obvious one – but for those who sweat the details, this evolution of the classic overnighter is as good as it gets. 

‘Diana’ Large Duffle by Gucci
‘Havana’ Sportscoat by Suitsupply

As the mercury rises and we all hang up our office garb for the remainder of the year, it’s a solid bet the fella you’re buying for will crave footwear that reflects his transition to greener pastures – at least, until Christmas is over. On the rare occasions when Craftsman boots might still feel a lick too dressy, Remy’s Sport Loafers ($395) are a fantastic stop-gap. With buttery suede uppers styled in three colourways – all of which look great alongside basically any of your sartorial staples – they’re a prime example of the intersection where elegance and simplicity meet.

Christmas Gift Guide menswear
Sport Loafers by REMY

No Christmas extravaganza down under is complete without countless days of fun in the sun and a dip in the proverbial big blue. For the man who embraces both, a slice of kit that will take him seamlessly from surf to sundowner is satisfaction guaranteed. Accessories with a practical bent – that never compromise on good looks – are the best place to start: whether it’s a robust Rodd & Gunn Signature Cap ($49) or the XT-6 FT Sneakers ($300) – Salomon’s giddily over-engineered solution to all your coastal hiking and jogging needs. For the man who will spend most of his holidays livin’ that life aquatic, make a beeline straight to the Venroy Printed Swim Short ($120): 9 patterns, inspired by the brand’s recent explorations of Marrakech, give you plenty of choices – him even moreso, when he realises these above-the-thigh numbers look even better paired with summer tees.

XT-6 FT Sneakers by Salomon

But what about the culture vulture? That dude who spends his festive season scouring the city’s cafes, galleries and Boiler Room tour dates? Rest assured, we haven’t forgotten about him either. For the inveterate fan of open-air festivals, you could do a lot worse than Sun Buddies’ Frank Sulfur ($200): eyewear with a timeless shape in contemporary colours, these will see him through many a parkland gig – and countless other settings besides.

On the feet, we know we’d personally never say nay to a crisp pair of New Balance: particularly when the aesthetic looks as relevant, and yet is as historic as the 574 Legacy ($180). While you’re at it, why not show some love to the drawstring trouser? Fast becoming a mainstay of Antipodean style, they’re a welcome addition to any wardrobe where well-worn sneakers and band tees reign supreme. The Tallow Stripe Linen Pant ($139.95), designed by homegrown heroes M.J. Bale, is a great introduction to the style. 

Where fashion stans are concerned, Casablanca’s ‘Soleil Levant’ Tracksuit Top ($425) is a nuclear option: luxe, pricey, and liable to generate hundreds of IG captions about ‘sending big fit energy’. From the Parisian brand’s SS22 collection, this shell track jacket conceals its intelligent construction with plenty of whimsical Japonism-inspired motifs.

‘Soleil Levant’ Tracksuit Top by Casablanca

For an aesthetic that eschews the runway in favour of Rocky, Boss’ Organic Cotton Logo Hoodie ($369) will have you fighting off those Christmas calories in next-gen style – thanks to the French terry sustainable fabric with an extra-soft feel.

Medium Utility Tote by Haulier

Last but not least, make sure you’ve got a present in the back pocket worthy of the ‘men about town’ in your life. For creative types who are forever between meetings, you’ll find few daily carries as competent as Haulier’s Medium Utility Tote ($525). The body is fashioned from 24. oz cotton canvas woven on old shutter looms. In this particular dimension, that means a carry-all that can do it all: offering ample storage for one’s working necessities, plus room enough for that last-minute detour to the bakery.

Melange Zip-up Hoodie by BOSS
This article features some sponsored inclusions from brands who have supported Boss Hunting throughout 2022.

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Randy Lai
Following 6 years in the trenches covering consumer luxury across East Asia, Randy joins Boss Hunting as the team's Commercial Editor. His work has been featured in A Collected Man, M.J. Bale, Soho Home, and the BurdaLuxury portfolio of lifestyle media titles. An ardent watch enthusiast, boozehound and sometimes-menswear dork, drop Randy a line at [email protected].


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