Vacation Edit: The Art of Destination Dressing

Vacation Style Edit: The Art of Destination Dressing

2/8/2016

Master the stylized art of tasteful destination dressing with this inspiring gentleman’s style edit + travel and packing guide

Vacation Edit: The Art of Destination Dressing (monk + eero)

Words + Styling ~ By Lyle Eero ~ 8 February 2016

hether by plane, train, or automobile, the reality of travelling for business or pleasure is simply a matter in which every gentleman must be sartorially prepared (and ably fit) to contend with in his lifetime. And while many see it as an enriching, cultured privilege that one should take great pleasure in — a commendable and worthwhile character building pursuit as it were — there are others who truthfully loathe it, viewing it as though it is the bane of their very existence — a necessary evil of sorts.

Nevertheless, it is most assuredly something we all must partake in as due consequence of one social calling or another, be it for recharging our proverbial batteries while escaping to the tropics, returning home to visit relatives during the holidays, or possibly even as ones business obligations and responsibilities would have it be so.

That said, what troubles most men is not the journey itself but rather the distinctive — destination prescribed — style parameters that (hauntingly?) accompany any scheduled port-of-call. It is the often perplexing what to wear and pack ordeals — and not the hours spent travelling, the varied cultural mores one is beset with, or the jet lag — that invariably cast a dark cloud of personal frustration and sartorial befuddlement over the otherwise enlightening nature of travel. And yet, it certainly is not all doom and gloom.

The good news? The world is your oyster, and either a relaxing vacation or the opportunity to further cultivate your gentlemanly being, intellect, and character awaits. The bad? You haven't the slightest idea as to what to wear. And seeing as you (likely) hold yourself to an elevated sartorial standard, I feel it should be safe to assume that you would not be satisfied with being yet another sheep who is content with joining the masses in sporting the type of stereotypical vacation and travel attire that is, to put it bluntly, simply deplorable in every sense of the word.

Having said that, it does indeed ring true that vacations are often solely about basking in sheer comfort, being expressly predicated upon the dispensing (shaking off) of ones everyday — often formal — chains in the name of relaxation and some form of perceptive casual opulence. But if truth be told, the pursuit of comfort is not a proper excuse for one to dress slobbishly. On the contrary, one can in fact cut a charming, stylishly sophisticated figure and still be comfortable all the same.

So, what precisely does one pack when travelling to look his sartorial best without neglecting his creature vacation comforts?

That is a question I'm accustomed to hearing often (albeit in different forms) .

Ordinarily, for many that means employing their roomiest leisurewear to best effect, but as previously noted that sort of approach and opinion on comfort + style will not suffice for you (nor I). So, where exactly does the gent who is adamant in his pursuit of always looking the proper part and unwilling to let his personal style slip under any circumstance begin?

Well, for starters his first task is to pack intelligently by identifying a single — often signature — personal staple essential that is socially versatile beyond compare, that is crafted of a fabric that suits the temperatures of the locale, and that he feels not only stylish while wearing but also comfortable. Once he's done that, he can then proceed to building a transitional capsule travelling wardrobe around it.

But before one can do that he must first carefully consider a few questions that will help in the process. Introspective style insights such as do you have a fail-safe piece that you always count on that can be put to good use as the pillar of your travelling wardrobe? And if so, what is it and does it translate well to the nature of the trip? Identified it, well then you must now ask yourself whether it is made for the destination (fabric, cut, lining, etc)? And, if you do decide to let your sartorial standards slip to the wayside, you must then ask yourself whether you can honestly live with the fact that you are letting your better sartorial self down by wearing something most unbecoming of a gentleman (such as socks with sandals)?

Beyond those initial personal considerations lie the ever influential destination specific questions that will ultimately dictate precisely what is required for the journey. These include such matters as the parameters of the trip (casual, romantic, formal), it's duration (day trip or and week long excursion) and scheduled itinary/activities (what do you need to do them), transportation (what forms will be used), and the unique environment and climate (tropical, metropolitan, etc.) of your port of call.

Seeking answers to all these variables will go along way in helping you settle upon a proper wardrobe for any given trip.

Having said that, editing ones travel bag down to the bare essentials can still undoubtly be a sartorial conundrum for some — a deplorably wasteful and beguiling triviality that leaves one frustrated and cast adrift, wanting for simply direction or even the smallest morsel of guidance.

But don't fret, because as fate would have it, today is your lucky day as this very feature was curated and crafted with the desire to placate any lingering doubts or questions percolating about your mind.

So whether your pursuits will have you skirting the golden tipped sands of a tropical locale, haunting the cobblestoned streets of Europe, or just simply flying in and out of any metropolitan urban jungle for a weekend business trip, here is what (and how) to pack to ensure you look as charmingly stylish as you are comfortable — that you look as good as you feel.

Why?
Because there is a definitive line that divides those who know how to dress for the occasion at hand in comfort and style and those who come off appearing as though they simply do not care nor should pay any such mind.

The following guide will help you fit in with the former and avoid the latter.

Henceforth, what you will discover in this feature ranges from the inspirational (three destination capsule wardrobe style guides) and practical (travelling advice + tips) to the insightful (cultured dossiers on three of the most critical travelling wardrobe investments a man can make)

ONLY QUESTION LEFT IS: WILL IT BE FOR BUSINESS OR PLEASURE?

Safe travels, good sirs.

The Tropical Escape

Casual comfort is the name of the game come the search for sun, surf, and sand. And seeing as one will invariably be dealing with the persistent heat and humidity of such locales, packing relaxed essentials fit for such conditions is paramount to ones luxury.

So, think materials like linen and cotton rather then wool or flannel (or worse yet, tweed).

With that, and the gent who has the sartorial aspirations — and the high personal style standards — of cutting a charming silhouette no matter the thermal reading, comes this destination capsule collection of stylized tropical wears.

Now, shall we dive in?

For the first of the curated looks above, I've opted for a natural — blues, browns, whites — palette that is built upon the timeless laurels and stylish nature of staple warm weather essentials that have been luxuriously upgraded to best befit the needs of the sartorially discerning gentleman. From the unstructured (and unlined) linen blazer (which can be easily be layered on and off to fit the occasion at hand) with its spacious patch pockets (to store anything nine deems pertinent), to the suave navy and white heritage houndstooth knit polo with cuffed hems and the swim ready (yet land appropriate) navy (mid thigh resting) signature Orlebar Brown side fastened shorts, this dapper ensemble simply exudes confidence and effortless comfort. Tack on an elegant trilby hat (to protect ones head from the sun) alongside some island appropriate canvas slip-ons (instead of sandals) and a NATO-strapped (navy + white) watch and what you have is a look sure to charm come day or night, surf or turf.

This look, although formal in spirit, ultimately personalities casual refinement at its warm weather finest, being stylishly nonchalant and comfortable, structurally breathable, and bewitchingly inviting all the same.

Alternatively, and for those whose desires stray even further towards the casual spectrum, comes the ensemble situated above right.

Anchored by an ever fashionable and on-point (and classic) cotton bomber jacket (chosen in tan/khaki here), this creative ensemble, which includes a pair of skinny white chinos, a cotton-linen button-down shirt, a nautical striped ring belt, tortoise shell Ray-Ban Clubmasters, and a pair of Breton-striped espadrilles, will have you looking and feeling like your Sunday best any day of the week.

Personal fancy aside, both of these highly presentable looks are poised to handling your sartorially inclined needs (and comfort) with ease.

Pack either or, or even both in order to create a multitude of mix and match ensemble options.

And to that I will simply say Bon Voyage and happy sailing to all my seafaring brethren.

What Else To Consider Packing : tan chinos + swim trunks + white tee + Breton striped long sleeve tee + dress slippers + formal trousers + patterned vest/muscle shirt + paisley short-sleeved fitted button up

Essential #1

: LUGGAGE :

Whether one is a seasoned jet-setter or an intermittent traveller, one thing he invariably requires is proper luggage befitting his journey ahead. And at the top of the list? A sturdy, transitionally versatile bag that maximises style and space while minimizing hassle.

But with so many options where does one begin his search?

My advice: look no further then the classic leather (or canvas) holdall. It's a triple threat delivering
— style, rugged practicality, heirloom quality -- timeless wardrobe investment that will pay back stylish dividends until the end of ones days (and beyond if properly cared for).

Not merely a superfluous adornment but rather a statement making lifestyle accessory, a handsome mid-sized holdall is just small enough to pass as carry-on luggage yet just big enough to ably pack whatever one requires, be it a weeks worth of clothing and toiletries or an overnight supply of essentials.

That said, it can also be put to proper use as an able wardrobe courier for the gentleman whose transportation itinerary warrants that he travel by sea, rail, or pavement, and not solely by air.

Have an impromptu romantic weekend getaway via rail in the cards? Or maybe it's a (lengthy) road trip within the tight confines of a space deprived sports car? Whatever the occasion, it can handle any situational or elemental parameters you throw at it, whether rugged or cosmopolitan in basic nature. Although, I would advise stopping short of making the ill-advised decision of using it as a gym bag to toss in your drenched fitness kit or moist towel into. It could certainly do the job, but you should have a dedicated bag for just such matters (like this).

The Takeaway: A quality leather holdall is an elegant status symbol worth investing in. A bag that is a cinch to transport, is structurally resilient and masculine, situationally versatile, and undeniably stylish beyond equal measure. It is simply a jack-of-all-trades bag, the ultimate luggage courier for the style-conscious travelling gentleman of this day and age who demands form, function, and style in one collective package.

Long Haul Alternative: A wheeled, hard-shelled carry-on size suitcase (such as this)

The European Explorer

Ah Europe, it's an enchanting mistress for all those who do not call it home, a far off dream that seems culturally familiar and yet stands so geographically distant. A destination most yearn to one day fully experience first hand: from exploring its reknowned cobble-stoned streets and indulging in its ethnically diverse signature cuisines to basking in its highly cultivated cultures and its storied history, architecture, and mystifying landscapes...

...it truly has an enduring draw and inviting quality that can tickle any proverbial fancy, so to speak.

So, what does one pack under the circumstances?

For starters, I'd advise calling into action your tailored bests. From ones formal wear to his casual staple essentials, having a travelling wardrobe filled with properly cut, fabricated, and tailored wears is of a chief concern when visiting Europe (where the average man's sartorial standard arguably stands a notch above anywhere else).

But why?
Because the small details matter (especially when speaking in regards to ones style), and by paying special heed to them you will be setting yourself upon the highly coveted path of effortlessly fitting in with the local denizens.

To help you accomplish just such a feat while venturing throughout the Meditteranean nations I've curated the capsule ensemble situated above (left). And seeing as this is the land that founded sprezzatura (Italy) and mastered the laid-back sporting-formal aesthetic, the piece de resistance is naturally the unconstructed linen-cotton double-breasted navy blazer, a versatile menswear staple essential in many parts that screams of subtle sophistication and masculine refinement. Top it off (literally) with a grey felt fedora, a navy striped dress shirt with contrasting white collar and cuffs, a striped (red/navy) pocket square and patterned tie, grey lightweight wool trousers, and a plush pair of navy suede loafers with contrasting red tassels in order to present a classy and elegant silhouette that plays towards the Pitti peacock aesthetic, albeit in a more tastefully delicate and sensible manner.

Smart, refined, and stylishly polished, it's a look sure to please.

The Travelling Workout Kit (monk + eero)

Not tempted by the pull of the Mediterranean and have your sights set firmly upon exploring further up north?

Well then, if France or the U.K. is on the ticketed docket then look no further then the monochromatic look to the above right — which will be equally at home in Paris or London. And your signature stylish linchpin for this destination: the black double-breasted military trench coat, which is not only utterly practical (against the cold and blistering elements alike) but markedly chic and as stylishly sharp as a needle.

That said, the tailored white trousers, sleek polished Chelsea boots, Breton-striped (black/grey) turtleneck, and knit (black) flat cap that round out this outfit are no sartorial pushovers either, being able to serve as statement making pieces that would pass as standalone stars on their own lauded merits.

Nevertheless, and as a conclusively unified entity, this ensemble exudes a very svelt and handsome David Beckham/Yves Saint Laurent vibe that is both highly regarded and sought after by many a man.

Not sold on the trench? Sport a black leather biker jacket instead to add a touch of rakishly rebellious charm to the look.

So there you have it, two highly polished (alternative) looks that will have you looking undeniably primp and proper whether seafaring through the Mediterranean or stomping about throughout mainland Europe's iconic streets and historic structures.

What Else To Consider Packing: Fitted t-shirt/polo & underwear (white, black, grey) + an additional dress shirt (white) + a shawl-collared heavy knit cardigan + dark indigo jeans (to pair with blazer for casual looks) + a few additional ties/pocket squares/socks (although one would do well in purchasing new ones while there instead) + a pair of chocolate leather monk-straps + an ascot or silk (summer) scarf + driving gloves

Essential #2

: THE DOPP KIT :

Whether storing essential toiletries or carrying reserve provisions and funding, a quality Dopp kit (or wash bag) should always deliver equally in style, form and function, being a requisite accessory for the gent who expects his luggage to look as sharp as his style and who wants to stay well groomed no matter where his travels take him.

Question is, are you looking to invest in a heritage quality type of kit that offers style, class and refinement in spades or something less frivolous albeit still as fashionable yet only more financially sensible?

If you count yourself amongst those who share the opinion of the former, then look no further then a kit crafted of leather, which not only ages gracefully — getting better with time — but is as ruggedly masculine and durable a material as one can find.

*Style Note: it is that very hallowed longevity and celebrated timeless appeal that sets it apart from it contemporary alternatives.

Need further reason to invest in a leather dopp kit? Well then possibly it's true clincher will sway you over: leather carries with it (showing in its patina as it ages) the experienced remnants of the many tales of adventure that it has been privy to over its lifetime…being a nostalgic inducing sartorial accessory that reminds one of the storied travels and accompanying tales he would care to pass along and regale future generations with.

Of the more fiscally inclined disposition -- the latter crowd? Then a kit made of canvas is really your only other reasonable -- and financially sensible -- option. While it does not look as good nor age as well as leather, canvas is however still able and up to the task at hand and should fit the bill admirably.

At the end of the day either option works, just be sure to steer clear of cheap polyesters or (worse yet) plastics at all costs. Not only do they look dreadful, but they perform in the same manner (and are prone to randomly falling apart).

With your dopp kit chosen, you may now be inquiring as to what precise essentials to fill it with?

Well, I've curated the graphic list situated above of the requisite grooming essentials to placate just such a question. It's a paired down checklist of items that should set you right — keeping you looking properly primp — for any adventure that awaits.

The Seasoned Businessman

Packing for a business trip requires a gent to prioritize his working wardrobe above all else. That said, just because the parameters of this trip dictates he conform to a more formal dress code does not mean he should not consider packing for more unofficial (after hours) social events as well.

The solution: A wardrobe consisting of three parts formal workwear and one part casual attire.

Beginning with ones tailored business wears (i.e. a suit), rather then opting for the same suit you rely upon day-in day-out, I'd advise electing for something a touch different, a new (or underused) suit that will undeniably mark — and add character — to the occasion.

My pick: an exquisite two-piece navy suit in a checked windowpane that is charmingly accentuated by a fine-gauge burgundy cardigan, a white (cutaway collar) dress shirt, and a red/blue paisley tie + white silk pocket square combination.

And the true difference maker? That would be the cardigan, which dispenses with any further formality (which a waistcoat/vest would add) while still serving as a work appropriate and transitionally versatile option — omit the tie and suit jacket to transform the look into charming evening attire fit for casual social gathering/dinner or after hour drinks.

With one's suiting needs covered, what else should he pack? I'd advise a smart mixture of business and pleasure essentials: 2 additional dress shirts (white & pale blue), a pair of double monks (instead of laced oxfords), a double-breasted camel trench coat (contingent upon the destination), a few casual t-shirts, socks, 2 pocket squares/ties, a thin turtleneck sweater (black or grey), and a grey pair of dress chinos.

Travel tip: wear your suit jacket (and tie clip...bypassing the need to dig it out of your luggage at security) in-flight so as to avoid any creasing or wrinkling in transport. Bonus: it will also allows you to be ready to step into the office immediately upon arriving.

Special packing considerations: laptop, tablet, document portfolio, chargers

Essential #3

: FOOTWEAR :

Gentlemanly Travel Essentials: The Loafer (monk + eero)

The loafer: the perfect travelling companion for the sartorially inclined modern gentleman.

But why the loafer?

That would be in due part to their seemingly unrivalled social versatility (smart + casual occasion appropriate), structured comfort, polished sophistication, and easy wearing nature — being a breeze to slip on and off at airport security, while on flight, or whenever one so desires.

Speaking solely in terms of style, loafers can be worn with or without socks (which is a matter of personal fancy) and simply look great with everything from your tailored suit to your favourite pair of jeans (or chinos/shorts), And seeing as you will be spending all your time in them it's only fitting that they are not only comfortably sensible but also charmingly handsome.

And, it is for those reasons that the loafer should be — whether chosen in a penny (upper left), tasseled (centre), or horse bit (right) form — the ideal option for the traveling gent.

In formative essence, they allow one to effortlessly navigate, transition, and stylishly toe any dress code lines that variably present themselves while one is visiting other parts of the globe.

The Takeaway: Loafers can be easily slipped on and off (to ease through security) and allow one to dress up or down for any occasion with refined panache and little effort (and all without needing to change footwear)..

Alternatives travel friendly options: espadrilles (instead of sandals in tropical locales) or brown Oxford brogues, dress slippers, or minimalist sneakers (purely for casual travel).

Parting Sentiments

Even the seasoned jet-setter or cultured adventurist would be hard pressed to disagreed with the commonly held belief that travelling in style can be quite an obstacle to overcome for the average man — especially if approached in an ill-advised or improper manner. But, and if this feature is to stand as a testament to anything, it would be that it's not nearly as impossible as many would have you imagine.

For you see, all it truly takes to travel with refined panache in tow is a little foresight, effort, and a plan to carry it all out with. That's not to say you will never not be faced with another befuddling outfit challenge when deciding what to practically pack but rather that you will be better prepared to etching out a reasonable (yet still stylish) compromise as consequence.

At the end of the day, I can only hope that this feature has provided just enough insightful advice and style inspiration to carry you forth towards enjoying and experiencing your travels in utter comfort and style, to improving your creative outlook and well-studied approach to wardrobe attiring for when the next opportunity for hitting the open road, air or sea comes calling out your name.

Travel & Packing Tips & Advice (monk + eero)

~ BON VOYAGE ~

THOUGHTS + OPINIONS

So what have you to say in he he matter of dressing stylishly while travelling? And where do you plan on visiting this year?

Weigh in and share below…

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