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Monocle’s guide to looking your best at every occasion: Six ways to master your wardrobe

Dear reader, my name is Pablo and I am Monocle’s man about town. I’m a gent for all seasons and have a wardrobe that always comes to my rescue, whatever the occasion. I never have a hair out of place (unless tousled is what I’m after) and am ever the dress-code nailer. Monocle’s editors have asked me to impart some sartorial rules to play by for six given situations – including what you’ll need to see you through a weekend away, a sport session (I always like to keep things nice and firm) and a day out in the city.

From the basics to set you up for the day to the white suit and leather-sole dancing shoes that will see you through the night, my rules for getting dressed pair common sense with recommendations for the brands that you need to know – usually picked up on my travels to Bangkok, Paris, Lisbon and Tokyo.

If there’s a connecting line in my approach to getting dressed, it’s investing wisely in well-made clothes that will last a lifetime. That is, admittedly, not ground-breaking advice. But it’s worth reminding yourself of this when the temptation to totally overhaul your wardrobe takes hold. Personal style is an art form that requires honesty and self-reflection. Is the shoulder on that white T-shirt as flattering as it could be? Do I have what it takes to pull off those shorts? Almost certainly… but it’s worth considering.

And never lose sight of wearability. Beautiful loafers will lose their appeal if they make you hobble. I’m also a believer in the idea that good clothes are not the main event but rather a support system for a life well lived. At its best, getting dressed is the first step in a day that is packed with places to be and people to see. Ready? Let’s go.

Illustration of Pablo, a bearded man holding a red patterned jacket and white shirt with decorative pockets on hangers.
Choices, choices. Faced with unlimited options, it can be hard to know where to begin your journey towards the perfect look for every occasion. Fear not: I have you covered, from head to toe.

Style tip 1: Perfect your basics

Starting from a strong foundation is key. Nailing socks, undies and beauty-cabinet essentials – unsung heroes all – requires as discerning an eye as it takes to pick out a statement coat.

Rise and shine
Starting my day in a pair of pyjamas from Spain’s Denis Camisería makes waking up feel like a main event. How to describe this feeling? The cat’s… whiskers.

Illustrated man in white shirt with arms raised, smiling confidently against pink background with yellow accent details.

Stay surefooted
There’s no better sensation than sliding toes-first into these tatami-and-leather slippers made by Japanese brand Liberato. Arch support is key to making great strides.

Illustration of two rust-red and navy leather slippers with textured soles hanging from strings.

Shower time
I grab my pillowy towels purchased on a recent trip to Japan. There’s no finer option for drying yourself off than those manufactured in Imabari.

Illustration of stacked towels in white, pink-dotted, and golden-yellow colors.

Precise flow
Bangkok-based brand The Oba makes the perfect shower gel with which to lather up under a high-pressure pump by German brand Dornbracht.

Illustration of a person showering with The Oba shower gel bottle and Dornbracht pump visible below

Keep it brief
Briefs or Y-fronts offer anatomical support and natural alignment without compression. Mey’s pants bring German engineering to the undergarment.

Illustration of hands holding open a white brief/underwear garment against a yellow textured background.

Debate at length
“High socks, high standards” is my motto – but there’s also a time and a place for a can’t-see-’em pair sourced from Muji. Otherwise, it’s Tabio.

Illustration of a confused person in a yellow shirt holding a red and black sock, with question marks above their head.

Winter warmer
New Zealand’s Icebreaker makes merino-fibre thermal shirts and pants that naturally trap in heat (an ideal ice-breaker for a first date with winter).

Illustration of a man wearing a rust-red Icebreaker merino thermal shirt and pants.

Cabinet of curiosities
Skincare products are as close to five-star treatment as I can get at 08.00. Chanel for fragrance and Nivea for deodorant is a fool-proof high-low combination

Illustration of skincare and fragrance products including Chanel perfume, Nivea deodorant, MALIN+GOETZ hair pomade, and other grooming items arranged on a pink tiled bathroom shelf.

Style tip 2: Look the business

The investors are in town so be ready. People often suggest starting with trousers and building an outfit from there – but where’s the fun in that? Pick a shirt and keep the slacks lacking for now. It’s showtime.

Get steamy
No, not like that. Ironing or steaming is the most effective way to elevate your outfit. Swedish brand Steamery makes a packable version that cleans your clothes while making them crisp.

Illustration of a man ironing a black garment on an ironing board.

Shirt and sweet
It’s a choice between an Oxford by New York-based Gitman Vintage or a linen number by Naples’ Finamore. Both are made from fine fibres that will leave you feeling au naturel.

Illustration of four white button-up shirts on hangers with yellow circular heads representing clothing options.

Knot to be
Not every day is a tie day but when you need to get knotted, elect for something chic. Milan-based Bigi Cravatte has a range to complement any shirt.

Illustration of two polka-dot neckties in pink and yellow with dark navy blue dots

Tailor made
Let’s hear it for bespoke. My suit by Swedish atelier Saman Amel is second to none.

Blazer glory
For something off the peg, the Ring Jacket from The Armoury or United Arrows’ double-breasted mohair never miss.

Illustration of a man in a pink houndstooth jacket holding a navy blazer on a dress form for tailoring.

Watch your step
If you’re pounding the pavement and your city doesn’t have clear skies, opt for a rubber sole. JM Weston’s 180 is best for a polished look, though I do have a penchant for a Paraboot lace-up.

Illustration of two pairs of shoes: black loafers with white trim on left, rust-colored lace-up shoes with yellow insoles on right.

Style tip 3: Sportswear essentials for your kit bag

How can you look dashing on a run? Ask yourself what you’re running from (a poorly dressed version of yourself is an excellent motivator). So before you get into your stride, let’s consider the following.

Cool runnings
Whether it’s race day or a gentle lap of the lake, catch me in head-to-toe Hereness. The Japanese brand’s Drytouch technology keeps its shorts and tops from clinging.

Illustration of a man jogging in a yellow t-shirt and red shorts with running shoes

A bigger splash
Swimwear label Arena makes the best gear if you’re not afraid of getting your kit off. It’s figure-hugging and shows off a little thigh. Don’t fret, you will look great.

Illustration of a hand releasing pink and peach-colored circles and curved lines in an upward dispersing pattern.

Hold court
Net a matching set with shorts and shirt by Palmes. And Notace makes the best all-rounder shoe, whether you’re on clay, grass or heading to the gym. Mine are Kotos in white and green.

Illustration of a man in white tennis attire holding a tennis racket with a brown wristband, against a pink circular background.

Slap on the wristwatch
You will need a timepiece that’s capable of taking a beating. The Aurelia Aurita by Swatch is as happy in the pool as on the pitch.

Illustration of a wrist wearing the Aurelia Aurita by Swatch sports watch with striped sleeve.

Top gear
Copenhagen’s Pas Normal Studios makes cycling wear that looks good even when you’re just a blur, hitting 45km/h on a steep descent.

Illustration of cyclist in yellow jersey and helmet riding black bicycle at high speed

Leading the pack
It’s Kyoto-based Ichizawa Hanpu’s Boston Bag made for Trunk – thanks for asking. And yes, it carries everything that you could possibly need – even a lightweight Goldwin jacket for the journey home.

Illustration of man jogging in red jacket, yellow shorts, and black pants carrying yellow Ichizawa Hanpu Boston Bag

Style tip 4: How to pack at pace

Time for a change of scene. I’m an advocate for life on the move – it keeps things interesting. When it comes to packing for a sunny escape, don’t overthink things. My list strips it all back to the basics.

Compact case
Having a well-stocked toiletry bag at the ready is the first step to a successful pack. I opt for a leather number by Viennese brand R Horns.

Full look
The combination of a white T-shirt from Kotn, cord shorts from La Paz and sandals from Hender Scheme is a winner. For trunks, it has to be Ripa Ripa.

Pack it in
My suitcase of choice is by Japanese brand Proteca, for its 360-degree opening system. Packing light is the only option – no more than what fits into an overhead compartment, please.

Illustration of packing essentials for travel including a sandwich, white t-shirt, red shorts, striped shorts, shoes, and open suitcases.

Wheel it
Monocle’s trolley tote is the perfect companion for a weekend escape. I secure it over my suitcase and always feel confident that nothing will slip out, thanks to its zip closure.

Illustration of a man with a yellow suitcase and white rolling luggage at an airport with a plane in the sky

Smarten up
Finally, I make sure to pack an effortless evening look for dinner or a sundowner. A shirt from Japanese label A Presse or French brand Arpenteur never strays from good taste.

Illustrated woman sitting under a tree with a wine glass, wearing sunglasses and casual summer clothing.

Style tip 5: Feel at ease in the city

You might not have an occasion to dress up for this weekend but being on home turf is no excuse for looking slapdash. You don’t know who you’ll meet or what’s to come. Let’s hit the town.

Dream coat
A good blouson jacket will go the distance with you. Mine’s a cashmere piece from Zegna in a fetching tan, though I have a dark indigo suede version too.

Selvedge the situation
Kaptain Sunshine is known for its outerwear but its denim is overlooked. It’s an everyday staple only matched by Luca Faloni’s cashmere weave jeans.

Illustration of a man wearing a cream blouson jacket and dark shorts standing in front of a red door.

Raise your head
Picking a “stealth wealth” cap is never as simple as people think. So just get the best one: Vienna milliner Mühlbauer’s linen cap should do.

Illustration of man wearing cap and dark hoodie standing outside storefront with yellow awning

In your own time
You can still be flashy while comfortable – and the Cartier Tortue is a case in point. Its delicate shape has been turning heads since 1912.

Illustrated hand wearing a Cartier Tortue watch with orange leather strap and cream-colored face.

Good in the hood
Was your jumper made on a tsuriamiki? I bet it wasn’t. The best sweatshirts are made by Loopwheeler on rare Japanese knitting machines that create soft, tubular fabrics.

Illustration of a person holding a vintage camera up to their face

Style tip 6: Life of the party

It’s time to cut loose – you deserve it. You don’t need a wardrobe overhaul every time you step out for the night. Sometimes, all it takes is a subtle change of sole or colour to achieve the right effect.

Keep it trim
Head to Cut Salon Ban in Tokyo or Bento in Lisbon, where you should ask for a classic Portuguese style that’ll make you look like you own a vineyard or a football team.

Illustration of a barber grooming a bearded man's hair in a salon chair

Scent and sensibility
After-dinner events are always a chance to turn it up with a louder scent. Fragrances from Wienerblut or Loewe are just the ticket.

Illustration of a yellow fragrance bottle with a white label and spray atomizer.

Dancing shoes
The right footwear helps me on the dance floor. It has to be JM Weston again – but now with a leather sole.

Illustration of a pair of black oxford shoes with white stitching and tan leather lining.

White nights
Put on a white suit. Yes, really. Unsurprisingly, the Italians do it best. Get one from luxury menswear brand Caruso and don’t look back (but do try to avoid spills).

Illustration of man in pale yellow suit holding wine glass, styled for evening occasions.

Suit up
I checked in with The Decorum in Bangkok, where I bought this double-breasted pinstripe number. Finally I own a suit that I actually want to wear to more formal occasions.

Illustration of a double-breasted pinstripe suit and separate dress pants on wooden hangers.

The post Monocle’s guide to looking your best at every occasion: Six ways to master your wardrobe appeared first on Monocle.

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