readed scheduling conundrums, unpredictable “acts of god”, persistent arm-to-arm space jockeying, exorbitant hidden costs, customary “luggage misplacements”, inescapably overcrowded accommodations…the classic road trip delightfully circumvents nearly all common plights of modern travel (and brings into question its perceptive convenience) whilst imparting upon one a truly unburdened sense of freedom (not to mention latitude of choice) that emboldens many to actively pursue comfortablysetting out upon four wheels to explore our vast terra firma en masse at our own discretion, pace and fancy (far) removed from the omnipresent spectre of conditioned travelling variables that simply remain beyond our agency.
Howbeit, and while those tasks surely warrant immediate addressing, the truth of the matter is that they alone needn’t be the main cause of a strain upon ones otherwise well cultivated sartorial persona nor of the desires of the discernibly rakish who can rest assured in the reality that not all hope is not lost in the fight for maintaining a certain sartorial standard of distinction in dress everywhere the open road takes you.
For you see, there indeed exists a plentitude of aesthetically pleasing road tripping assemblages worth referencing that proactively eschew the status quo of lazily adopting sartorially unfulfilling and aloof wears that are atypically worn strictly in the name of either comfort, a misappropriated perceptive need, or simply as consequence of a general lack of personal effort.
No sir, enjoying the (arguably) most self-satisfying means of travel in life (with personal respects to sailing) erstwhile draped in scrubs should never be deemed acceptable. On the contrary, it should be imperative that a gentleman always be dressed in a flattering manner that is at once practical, approachable and handsomely chic whether destined for a quaint (and sparsely populated) countryside village or a bustling metropolitan hub; That road tripping, in spite of its laid back temperament and nondescript enterprise, is not the place for either unbridled sartorial aloofness: (i.e. wearing ill-fitting joggers and unlaundered t-shirts) nor of overly stuffy pretentiousness in dress (read: donning a travel suit) but rather a worldly sartorial fluidity that proffers a calculated balance between smart and casual with respects to helping one attain an equability of supreme comfort, style and utility in all that he (or she) wears.
Framed in such a sartorial capacity, hitting the open road (regardless of one’s styling preference or chosen tribe) can prove to be one of the most relaxing, fulfilling and liberating of all holiday getaways; An adventure held in high regard as a (generational) right of way for some, a therapeutic escape for others, and a life-altering experience for all involved should the magical prospect of each trip taken making for a completely unique journey unlike any other be factored in.
It truly is invigorating, romantic, liberating… and even notably stylish if approached in a sartorially apropos manner respective of the conditional road awaiting ahead — from rustic serpentine pikes and scenic coastal byways through narrow mountain passes or everything in betwixt.
To wit, my point being is that one can indeed look good and feel comfortable for hours in the drivers seat without any residual tradeoffs given there exists an entire plane of exceedingly rakish and tasteful road tripping ensembles awaiting reference that take great measure in adding an aura of distinction and endearing memorability to one’s wholesale experience on the open road — looks that are at once fit for purpose, stylish and comfortable.
Venturing beyond the (arguably) blasé and de-facto uniform of a simple t-shirt, sneakers, utility jacket and jeans (should that classic quadrant prove too underwhelming or cliche), what essentially follows below is a well-rounded display of how to look good while likewise feeling as equally at ease and well-prepared for whatever speed bump presents itself.
Having said that, in my humble opinion the ideal road tripping attire will remains to be (respective of ones prevailing sartorial predilections) tailored wears utterly fit for purpose that are culturally sensitive (read: inoffensive/in accordance with local custom), wholly presentable and capable of both instantly speaking volumes about who you are as an individual (i.e. expressive of your tastes/sense of style) and blending in wherever you go; Wheelhouse wardrobe staples, in other words, preferably in versatile (neutral/natural) colours guaranteed to deliver a reassuring dose of security and timeless style all the while excelling in fulfilling the role of proverbial cherry atop a perfect trip that otherwise has every desirable a gentleman could ask from his ultimate automotive experience — good views, fine company, palatable music, exquisite cuisine and unique cultural experiences.
Taking all that into account, when selecting your wardrobe (or but a single look) for your next (or any) road trip it would be advantageous to not only etch to memory the advice above but to heed the following as well:
Inasmuch championing sartorial experimentation whilst making full accommodation for any (and all) of your personally sacrosanct travelling bits and bobs (read: the worldly wardrobe essentials that you never venture abroad without), you could honestly say it makes for a holiday with an enduring appeal that speaks most intimately to those who harbour an inherent love for driving that is punctuated by a general distain for dress codes (read: gents who revel in being gifted sartorial carte blanche) and a seemingly insatiable lust for the sort of boundless exploration that can only be tamed by the overarching feeling of pure unadulterated escapism being framed by “take away your breath” grandeur, the promise of (self and worldly) discovery, and the ability to proceed at your own pace and with everything you need safely stored away in the boot of your car.
All that having been said, one could argue that as we bookend our transition from the sweltering Dog Days of Summer into the all-encompassing sensory overload known as Autumn that there is arguably no better time of the year (especially when factoring in the roads/sights becoming less sparsely populated as we speak) to answer the (revving) siren call of the open road than now whether you arrive with a desire to hit reset on life, enjoy its pleasures at a different pace (and in a different gear), or to simply explore the mysterious terra incognito whilst making good on that life-altering journey you’ve always fancied taking.
To that end, do consider this feature to be an automotive call to arms of sorts that aims to (hopefully) help better inform road trip initiates upon how to prepare, plan and (rakishly) orchestrate the ultimate road tripping experience post haste whilst stressing upon the importance of coopting a nuanced marriage of smart-casual dressage marked by transitional merit that renders it utterly fit for purpose.
Insofar as that, I’d certainly be remiss should I not briefly touch upon the reality that road trips are not always what they are cut out to be; That yes, they too can also prove (in spite of the romantic veneer) the root cause of unwanted duress with much being derived from the planning process in and of itself (not to mention the logistics and unquantifiable intangibles therein) wherein the sheer amount of options and decisions at play — where to go, stay (if applicable), eat and what to do alongside pack and wear -- can quickly overwhelm and cause both personal anxiety and mental strain.
Taking that into account, it nevertheless stands to reason that the lifeblood of all (great) road trips invariably rests in the planning phase and securing clothing that will ensure you remain not merely comfortable be also aesthetically self reassured. My point being is that before one can rack up the miles and snap those postcard worthy sights you must first-and-foremost (whether the trip is spontaneous or not) put in motion a plan that begins with selecting a route and destination and ends with settling upon an automobile, budget, itinerary and (last but certainly not least) a wardrobe capable of tying everything neatly together in a charming manner that befits the occasion and illustrates that while dressing down for a road trip may sound simple enough, looking casually rakish whilst doing so surely requires forethought on how silhouette, palette, texture and weight each factor in to helping you effortlessly straddle those hairpin curves in unwavering comfort and style.
There are, after all, a litany of grand automotive experiences awaiting beyond our desks that deserve an elevated sartorial touch; a whole world of opportunities and marvels just begging to be explored and simply enjoyed (and yes documented if one must) — journeys where the experience and scenery instantly take centre stage for good reason.
And so it is in taking both that into consideration alongside the desire of making sure you make the most out of your hard-earned and hands-on adventure that this guide wades through the vast collections of wears and garments continually vying for your attention with the singular goal of presenting a tasteful variety of functionally rakish articles of clothing worthy of investment that will not only appeal to the discerning eye and sartorial soul but also capably hold their own through thick-and-thin for years of road trips to come whilst providing assurance that each restorative sojourn taken is as notably stylish as it is experientially memorable.
To that effect emblematic of the ideal that the best foot forward rests in picking-and-choosing (as per ones needs) from a choice selection of timeless, handsome and versatile wears that are tailored to perfection with a roomier — albeit still flattering — fit in mind, what this sartorially infused primer ultimately makes for is a romantic ode to all the intrepid automotive wanderer’s amongst us who enjoy the simple pleasures of careening around hairpin corners and exploring the (relatively) unknown in a state of unwavering sartorial satisfaction with nothing but the power of four wheels leading us forward; A crowning sartorial ballad for those who either yearn for the unfettered freedom and romantic nostalgia road trips have become characteristically renowned for, who grew up in a family whose preferred weekend tradition was piling up in the car for hours of peak adventuring, or who desire an alternative means of eschewing the obligations of everyday life whilst turning back the clock on a present day-and-age marked by cheap airfare, technological over-dependency and a false sense of travelling convenience that have all but minimized the joys actively derived from taking in picturesque views, frequenting charming cultural stopovers, and exploring all the hidden gems a route has to offer.
As for where should you should plan an escape?
Well, the iconic (bucket list worthy) routes espoused upon below will surely rouse excitement and inspire wanderlust, but the truth of the matter is that a road trip anywhere should suffice in proving to be the perfect antidote to the stresses of life granted you ascribe to the belief that it is the journey (and experience) rather than destination that matters most.
So, whether its a well-trodden local path or some far-flung locale ensconced in mystique and intrigue beckoning you forth, herewith is the essential road tripping wherewithal every gentleman would do well of apprising himself of alongside four specialized road trip wardrobe capsules curated with an equability of form and function at the fore that will raise the sartorial stakes while you enjoy the unique freedoms of road tripping for a lifetime to come.
All that remains is scheduling time off, planning a route, securing transport, packing your bags, and simply setting off.
But why now?
Perhaps because father time indeed waits for no man (nor woman) so venture forth ladies
and gents with both an adventurous spirit and a hearty wardrobe in tow worthy of the occasion
as I promise you will not regret it…
ternally perched atop the bucket list of many a petrolhead and gentlemanly
lothario alike, the well trodden (and cinematically immortalized) coastal Amalfitana and Côte d’Azur (not to mention the lesser known Dalmatian Coast) are revered seaside hot-spots in eternal vogue that will forevermore remain steeped in both an intoxicating aura of romance and an unrivalled state of sartorial bliss.
In a strict sartorial capacity renowned as a stomping ground of gentlemen of impeccable style and sartorial gravitas whose superlative (and permanent?) state of divine Neapolitan dressage is at once inspired and enviable, true practitioners of true Italian sprezzatura (read: effortless elegance) if you will, one could argue that the heightened sartorial prestige of this regions denizens has an appeal and draw equitable to that of its layered cultural tapestry of cascading lemon groves, cobblestoned cities, rolling cliffs, pastel-hued villas, pristine emerald seas, and quaint fishing villages.
It is, if you will, profoundly hedonistic, a sartorial haven which demands you arrive dressed to (casually) impress with respects to channelling the distinctive air of sartorial nonchalance (or insouciance if you will) that permeates throughout.
Howbeit, why not stylishly toe the prevailing smart-casual line therein by pairing an apropos pair of suede driving loafers (for supreme feedback upon brake, throttle and clutch without slippage) in a washed-out tan suede hue alongside a de rigueur stable of al fresco evergreen Italian sartorial flourishes fit for the occasion.
Not to be lost in the shuffle, and also warranting inclusion in ones extended Riviera-bound road trip wardrobe capsule, is that of a softly-tailored (i.e. unstructured) summer-weight safari jacket (a cropped suede bomber would also suffice) to layer on should there be a nip in the air or an occasion arrives that calls for it.
Beyond that, I’d also advise packing a pair of plain white tailored swim shorts, a smart light-gauge heather grey merino/cashmere blend turtleneck (or louche short-sleeved cuban collar shirt/Breton-stripe pullover) and suede espadrilles that can be sported together as an alternative (or as separates) should you find yourself struck by a burning desire to either cool down in the water or explore the scores of idyllic beaches, ruins and luxury boardwalks en route.
En masse, this decidedly smart, considerate, cool and confident wardrobe is poised to play off with immaculate effect in helping any road trip bound gentleman effortlessly transition from drivers seat and beachside lounger through roadside eatery and heritage after heritage site with ease, aplomb and nary a break of sweat upon his brow.
From top to bottom championing a spezzato derived marriage of functional flair and transitional decadence in ones sartorial comportment, it certainly stands to reason that when all the dust settles upon your journey that it would be difficult to rally against the merits of this wardrobe being the perfect sartorial foil for any coastal road trip backdropped by the divine opulence of the French Riviera, the immutable romance of Italy or the understated beauty of the Dalmatian Coast wherein even the smallest of pleasures (culinary, tailoring, etc) are known to be not merely savoured in the moment but celebrated (and deliberated upon) over time and space.
Molto belle indeed!
Case in point: Scotland’s borderline supernatural — as well as equally sun-drenched and wet -- NC 500 and its promise of a sensory road trip back through time.
Earmarked by naturally stunning, remarkably desolate and otherworldly landscapes, mystic Isles of lore aplenty to traverse, and sharp winding (and windswept) mountain passes evolving into (surprisingly?) stunning beaches and picturesque coastlines, the ever-popular North Coast 500 highway is a drivers paradise that tables a tantalizing mixture of the new and old (the prehistoric in fact) so as to appeal broadly to a variety of tastes and desires — from crackling sandstone cliffs and (unexpectedly) pristine beaches primed for a splash through quaint fishing villages, whiskey distilleries and haunted castles by the handful calling out your name as if they were the sirens of Odyssian lore.
Be that as it may, it warrants immediate note that what it promises in sites, sounds and experience is always accompanied by very specific sartorial demands so to speak — especially if travelling in the autumn or spring (which I propose rather than the busy summer season) -- that more often than not require a specialized sartorial approach be taken that sees you taking great care in being mindful of your prospective surroundings and needs (as opposed to being a slave to trending fashions) with the net result ideally being a wardrobe equal parts refined, comfortable, hardy and robust; One spearheaded mainly by traditional heritage wears crafted from natural (insulating + moisture wicking) fabrics that were purposefully selected for their timeless versatility in wear, sharp characteristic finish and faultless evergreen sartorial standing.
To such an end, I’m of the stern belief that one can never go wrong in channeling the sportswear heritage and distinctive hues of the adjacent countryside — think subtle tans, greens, browns, oranges and reds -- in his choice of attire whether that entails leveraging autumnal tones such as amber and russet upon his be-speckled tweed sports coats, casting his gaze towards richly fabricated performance wears of enduring sartorial standing such as natural merino wool turtlenecks, or simply falling back and relying upon a faultless contingent of hard-wearing garments such as cotton-twill chinos (denim doesn’t breathe as well) and leather water-proof driving loafers (with crepe-soled/Goodyear-welted suede chukkas in reserve) that have earned countless accolades en route to obtaining permanent wardrobe staple status for good reason.
As disheartening as that may seem, and as tempting as it might be to ‘pack and dress lighter’ for your bucolic jaunt through the untamed countryside, your best bet henceforth would be to (first-and-foremost) be proactive in securing the aforementioned foundation pieces before weighing up the applicational merits of those in which you plan to secure in reserve — travelling blankets (for impromptu picnics), tweed sports coat, extra socks, smarter dress shirt (for smart dining), simple merino wool t-shirt -- with respects to curating a well-rounded wardrobe capsule which will ensure you are properly dressed whether the weather turns for better or worse.
With that in mind, may I suggest wearing the traditional British waxed field jacket headlining ensemble below whose tried-and-true foundation of masterfully layered wheelhouse staples is at once practical, rustic and formidable?
Prioritizing wearable utility rather than superfluous fashionability, this look consists of hardy country-inspired wardrobe totems capable of serving as lifelong companions as consequence of owning a tactile ruggedness and sartorial fortitude in wear that is backed up by an assurance of being as hard-wearing, wholesome and functional as they sharp, considerate and discerning. From the chunky wool turtleneck sweater and (fully lined) leather driving gloves (for a greater experience marked by added control, feel and warmth) through the aforementioned lightweight (so as to not overburden),water-resistant cotton waxed field jacket (whose abundance of pockets and roomy structure make allowance for building breathable layers beneath), sturdy yet smartly fitted cotton-stretch chinos (cords would work as well) and suede horsebit driving loafers (pack suede chukkas/desert boots in reserve for “activities”), this formidable look goes above and beyond in channelling the spirit and endearing heritage of the countryside in its every nuanced thread.
Taking everything into account, what this capsule does best, aside from proving itself exceedingly fit for purpose as well as equally convincing in a sartorially sportive yet distinguished capacity, is illustrate why a weekend sojourn into the Highlands (or your hometown’s nearest countryside) needn’t be the cause of letting ones sartorial standards slip.
As for the raw and visceral excursion in and of itself, not much else can be added other than that while the NC500 can surely prove challenging (most notably to novice drivers) and time-consuming (the posted speed limits often waver below 50/km on many roads) its jaw-dropping beauty, old world feel, and breath-taking twists and turns offer everything a gentleman could possibly desire from a (top tier) road trip from stunning vistas, unique off-road detours, sparse crowds and superb dining options through dark age castles, quaint lochs and that quintessential feeling of a delicate balance being struck between engrossing culture, absolute freedom and a (highly stylized) life-altering experience -- driving paradise par excellence.
hould you be drawn to the artistic pedigree, beach bum culture or eternal sun of the freewheeling “Land of Milk and Honey” do venture west for a storied surf-and-turf road trip postmarked by a blanket of rocky enclaves of immortal stature, coastal byways of postcard notoriety, rolling beaches of pristine beauty, and traditional roadside eateries ensconced in nostalgic lore that invite you to explore at will whilst embracing a sense of spontaneity far removed from the scope of everyday mundanity and obligation.
Deemed summer’s answer to the traditionally peacockish smoking jacket, this completely machine-washable yet luxurious, charming and elemental modern sartorial totem is undeniably fit for purpose, highly covetable and more than capable of capturing the spotlight whether deployed in unity with a classic American button-down pima cotton shirt, white canvas trainers and tailored swim shorts (mid-thigh in length) or alongside light (or perhaps dark) rinse denim jeans (rolled up to mid-calf) and a simple white cotton tee for a more down-to-earth go anywhere look.
Simple, streamlined and just a touch rakish, this delightful blazer was designed to maintain its sartorial polish, immutable sense of comfort, and characteristic charm worn anywhere from casually in the driver’s seat and more formally upon the boardwalk through sportively at the beach — so feel free to wear it however you see fit.
Beyond that, simply bookend any look(s) crafted therein with classic wayfarers and a surf-ready diving watch so as to tackle or navigate any challenge — surf or turf — tendered along the PCH with peace of mind and sartorial aplomb.
Profoundly synergetic and easy-going, you can undoubtably wear any of these pieces interchangeably (gussied up or down) with the goal being of continually channelling the quintessentially relaxed vibe present throughout the Golden Coast without ever stereotypically venturing into either Cali (poncho wearing) beach bum or double-denim Americana territory.
At once comfortable, breezy, smart and sleek, what more truly could a gentleman
demand (or command) from his (beach bound) road tripping attire?
ALSO WORTH BRINGING…
picnic basket | solar electronics charger + car battery maintainer | flashlight | dry food rations + water
| umbrella | reusable shopping/tote bag | reusable water bottle | motoring blanket | folding chair |
jump starter kit (+ How To Jump Start A Car) | facial wipes | travel atlas/maps + compass | dopp kit | key finder
That having been said, this comprehensive road trip primer dutifully champions the road trip as a holiday wherein just such a transitional fluidity and (geographical-driven) experimentation in dress were set out to be wholly encouraged.
And so it was with that ideal in mind that I took to crafting this guide (for inquisitive clients and readers alike) like a fish to water with a discerning eye strictly cast upon referencing the automotive styling nuances (and predilections) of a choice selection of rakish gentlemen of days past and present who are (or were) renowned for having a firm grasp on how to traverse the planet whilst behind the wheel in sheer utter comfort and unwavering style.
And the result?
Four (destination-specific) road trip wardrobe capsules each maximized to appeal to a broad spectrum of tastes, primed to transitionally broach new sartorial territory (and terrain), and curated to pay homage to such luminary road tripping savants as Messrs McQueen, Grant and Gandy who’ve demonstrated (time-and-again) how one can best proceed to injecting a heightened touch of class, polish and distinction into ones road tripping attire without needing to sacrifice upon comfort nor functionality in due process.
To wit, each “wardrobe capsule” above is essentially an illustrative blueprint of how to tastefully marry the worlds of classic automotive styling and modern tailoring with the overall goal an appealing set of looks capable of embodying the “spirit of motoring” that are completely fit for purpose, easy-wearing and approachable all the same (perhaps the sartorial road less traveled for many a budding petrolhead?).
Richly strewn with faultless transitional wears of unwavering aesthetic appeal and respectability while contrastingly deprived of superfluous sartorial fodder and fashionable crassness, what each refined wardrobe backdrop excels at herein is in effectively ensuring any worldly adventure(s) embarked upon whist sartorially endowed with their presence will be of the peculiar ilk worthy of lifelong posterity and retelling — experiences destined for the ages.
To that end, and respective of however you’ve come to perceive or regard road tripping in and of itself, if there is indeed one thing that remains constant about it come each subsequent sunrise and sunset it would be that it is a completely objective experience unlike any other that has continually proven itself to be as equally pleasurable and self-fulfilling as it is enlightening and invigorating. Or, and more succinctly, it is the perfect way to hit reset on life while exploring the hidden wonders of the world at your own pace and discretion.
Howbeit, maybe you’ve already outlined your next excursion, or maybe not, either way here’s to succumbing to the romantic nostalgia of the occasion, to revelling in Mother Nature’s natural tapestry in transit, and to dressing rakishly whilst completely immersing yourself in the freedoms and ambiance of your chosen journey, route or destination whether you are tracing the Pacific Coast highway’s iconic stops, careening around nail-biting hairpins in the Cote d’Azure, experiencing all four seasons along Japan’s Golden Route, or revelling in the old-world mysticism of the Isle of Skye (and its quaint rustic succession of country villages and fishing ports therein).
Because road trips remain life-altering experiences that, when supplemented by good music/informative podcasts, comfortable clothing, fine company and the contoured pleasures of a performance automobile at your every beck-and-call, have a tendency to linger on in memory for decades; Holidays (or perhaps habitual pursuits for some) that are arguably always best underscored by a characteristic desire to cut a rakish automotive dash wherever the road takes you so as to all but guarantee the journey is truly unforgettable and earmarked for posterity in high style.
And should those enticing prospects — freedom from obligation, unrestrained latitude of choice, sartorial carte blanche — not strike a chord then I’m perplexed as to what will. What I do know, however, is that road tripping will surely continue to inspire wanderlust in the hearts of gentlemanly petrolhead’s worldwide who appreciate its unadulterated freedom of choice, the whimsy that arrives with spontaneously discovering the unknown, the thrills of putting petal to medal, the relief and clarity proffered by escaping daily routine, and the opportunity to take in all the unique natural sites, sounds and smells of the world dressed as they please.
The world, after all, is a vast, diverse and pristine pearl begging for the sort of exploration that only a car (and variety of culturally sensitive looks) can deliver upon; An ever-evolving entity (just like ones sense of style should be) whose every hidden treasure (and nook and cranny) is calling out your name as we speak.
Beyond that, well I’d simply just like to sign off by reminding you to remain steadfast in your pursuit of taking great measure to plan (but not over-plan) and dress most appropriately while remaining open to getting lost (within sensible reason) along the way as you never know what you will discover on route seeing as road tripping will admittedly open your eyes to new experiences (and perhaps sartorial cadences) in addition to leaving you reeling, reminiscing and day-dreaming about your next sojourn before the dust can even settle upon the last.
Oh, and do remember to keep this little nugget of advice in mind when embarking upon the initial planning phase: “in for a penny, in for a pound”.
As always, travel safe (and stylishly) ladies and gentlemen!