If you wear these 9 clothing items on vacation, you will instantly look upper class

Vacations have a way of magnifying our style.

Maybe it’s the golden light, maybe it’s the photos that live forever, or maybe it’s the simple fact that you’ve finally stepped off the treadmill and want your outside to match the inner exhale.

Here’s the good news: looking polished on a trip isn’t about labels or lugging a second suitcase. It’s about choosing a few elevated pieces that quietly signal quality, ease, and taste.

Below are the nine items I reach for when I want that “effortless, of-course-I-belong-here” energy—whether I’m poking around a farmers’ market in a seaside town or slipping into a tucked-away restaurant for dinner.

And if you’re wondering, yes—these work whether you love color or live in neutrals, whether you’re a carry-on-only person (hi!) or you like options.

Ready?

1. Crisp linen button-down

I start every vacation with a linen button-down.

Why linen? It’s breathable, it drapes beautifully, and the texture looks expensive even when it isn’t.

Wear it open over a swimsuit, half-tucked into shorts, or buttoned up with sleeves rolled for dinner. I pack white and one soft color—sky, stone, or blush.

If you’ve struggled with linen’s wrinkles, join the club. I used to fight them; now I lean in. A quick steam or a shake-out on a hanger brings it back to that easy, upper-crust rumple that says, I own an iron but I’m on vacation.

Pro tip: size up one if you want that relaxed, borrowed-from-a-boutique look. And skip chest pockets—they can skew casual.

2. Unstructured blazer

Nothing transforms a travel outfit faster than an unstructured blazer in navy, stone, or soft black.

The key word is unstructured: no heavy lining, no sharp shoulder pads, just a breathable weave (cotton-linen or tropical wool) that glides over your clothes.

Throw it over a tee and tailored shorts to board a ferry; shrug it on at dinner over a midi dress.

You’ll look instantly put together without trying too hard. As Tom Ford put it, “Dressing well is a form of good manners.”

A blazer is the quickest way I know to say “I respect the setting” while keeping your personal style intact.

3. Tailored shorts (or linen trousers)

There’s a world of difference between “vacation shorts” and tailored shorts.

I look for a flat front, clean waistband, and a slightly longer inseam (7–9" for most frames). Choose a midweight cotton twill or linen blend that holds its shape.

The silhouette should skim, not cling.

Not into shorts? Swap in straight-leg linen trousers with a crisp crease.

They lengthen the leg and telegraph sophistication, especially with leather sandals or loafers. The rule here is fit: neat through the waist and hip, with no pulling at the pockets.

If the hem hits just above the ankle, even better.

4. Breezy midi dress

I call this the “one-and-done” piece. A midi in a breathable fabric (linen, cotton voile, or a silky cupro) is as comfortable as pajamas but photographs like a dream.

Look for a simple neckline, a defined waist (belts help), and movement in the skirt.

Solid colors read most refined, but a small-scale print—think micro-florals or a subtle stripe—can be lovely in coastal settings.

I wear mine with sandals by day, then add the blazer and a silk scarf at night. Done.

It’s the vacation version of compounding interest: one piece, many elevated outcomes.

5. Structured straw hat (Panama or fedora)

A floppy beach hat feels… beachy. A structured straw hat looks chic.

A true Panama (handwoven toquilla straw) or a clean fedora shape provides sun protection and instantly lifts a simple outfit.

The crown should flatter your face shape (teardrop crowns are universally kind), and the brim should be wide enough to cast a shadow without overwhelming your shoulders.

I pack mine in my carry-on by stuffing the crown with scarves, then nestling it upside down among soft clothes. It arrives ready to mingle with oysters and sunset.

6. Minimal leather sandals

Leave the rubber flip-flops for the pool. A minimal leather sandal—two straps, a sleek ankle wrap, or a refined slide—elevates everything.

The leather patinas over time (the chic kind of aging), and the lines stay clean. Choose tan, chocolate, or black to match your bag or belt.

Comfort matters. Look for padded footbeds and flexible soles.

Upper-class polish isn’t about suffering; it’s about pieces that carry you through a long, lovely day without a blister in sight.

7. Loafers or driving mocs

I always add one closed-toe shoe that’s smarter than a sneaker but not as formal as a heel or Oxford.

Loafers—penny, horsebit, or a slim Belgian style—bridge that gap. In resort towns, a suede driving moc works too, especially in taupe, sand, or navy.

They pair with shorts, trousers, and dresses alike, and they’re ideal for flights: easy on, easy off, no laces to wrangle at security.

As Vivienne Westwood famously said, “Buy less, choose well, make it last.” Quality loafers can serve you for years of vacations.

8. Silk scarf

This is my secret weapon. A silk scarf takes up no space and does ten jobs.

Tie it at the neck with a white tee, thread it through your belt loops, twist it into your hair on a windy boat ride, or loop it on your tote for a little color.

Silk catches light beautifully in photos and adds sophistication to the simplest clothes. If you’re scarf-shy, start with a 70–90 cm square in a muted palette that echoes your wardrobe.

Fold diagonally, roll loosely, knot low. Voilà: effortless polish.

9. Quality sunglasses

You know when someone walks into a café and you can’t quite place why they look expensive? It’s often the sunglasses.

Look for a sturdy acetate frame, well-finished hinges, and lenses with proper UV protection. The shape should complement your face (softly squared and classic cat-eye frames flatter many).

I bring one versatile pair in a neutral frame, then sometimes add a second, slightly bolder pair for daytime exploring.

And please, skip obvious logos. Let the silhouette and craftsmanship do the talking.

How to pull it all together (without overpacking)

A few principles turn these nine items into a capsule that works anywhere:

• Choose a palette. Neutrals with one accent color keep everything mixable. Stone, navy, white, and tan with a touch of sage or coral is my personal sweet spot.

• Mind the textures. Linen, straw, suede, silk—when your fabrics are tactile, even simple outfits feel layered and luxe.

• Fit is the flex. Wealth whispers through tailoring, not labels. If a hem or waistband isn’t perfect, a quick visit to a tailor before your trip pays dividends.

• Edit your extras. A leather belt, a slim watch, and delicate jewelry (studs, a fine chain) are enough. Over-accessorizing can dilute the effect.

• Plan your airport outfit. I fly in loafers, tailored trousers, a tee, and the unstructured blazer. The linen shirt goes in my tote in case the plane turns into a refrigerator.

A note on mindset (and manners)

Style is a story you tell about yourself.

On vacation, that story can be calm, curious, and open. I’ve noticed that when I dress with care, I move with care.

I linger over conversations with market vendors, I ask better questions at the winery, and I get invited into places I wouldn’t be otherwise—if only because I look like I’ll appreciate them.

“Style is a way to say who you are without having to speak,” Rachel Zoe said. Clothes don’t make us—but they do introduce us.

When your choices are simple, well-made, and considerate of the setting, you’re signaling that you’re there to enjoy, not to perform. That reads as upper class in the best way: gracious, unhurried, and at ease.

Packing checklist summary

Here’s the quick recap you can save to your notes app:

1. Linen button-down (white + one soft color)

2. Unstructured blazer (navy, stone, or black)

3. Tailored shorts or straight-leg linen trousers

4. Breezy midi dress (one-and-done)

5. Structured straw hat (Panama/fedora)

6. Minimal leather sandals (neutral)

7. Loafers or driving mocs

8. Silk scarf (versatile size)

9. Quality sunglasses (UV-protected, sturdy frame)

Round it out with a compact steamer (or confirm your hotel has one), neutral underpinnings, and a tote that can handle beach-to-bistro duty.

Final thought

If you remember nothing else, remember this: simplicity plus quality equals presence. Choose breathable fabrics that flatter, silhouettes that skim, and accessories that feel deliberate.

You’ll spend less time fussing and more time savoring—which is the whole point of getting away.

Happy travels—and may your linen always wrinkle in the chic way.