Elegant Summer Outfits for Wine Tastings & Weekend Getaways

Old Money
Written By Damn You Look Good Daily

If your outfit isn’t pairing well with the pinot, then girl—we need to talk. Whether you're clinking glasses in Tuscany, sipping rosé in Napa, or fake-laughing through a vineyard tour with your friends just for the pics (no shade), this guide has your back. We’re styling that Old Money Aesthetic with a splash of Soft Luxury and a twist of Summer Chic. Because when the dress code is “rich, but relaxed,” you better not show up looking basic.

Let’s uncork the classy and serve some looks.

📚 Table of Contents

  • 🍇 Vineyard Outfit Essentials: What to Pack for Wine Season

  • 👒 Classy Summer Looks for Wine Tastings

  • 🧺 Casual Chic Vineyard Outfits That Still Slay

  • 🇮🇹 European Vineyard Aesthetic: What to Wear in Italy & France

  • 🥂 Accessories that Scream “I Vacation in Bordeaux”

  • 🛍️ Shop the Look: Links to Steal the Style

  • 📸 Bonus: Pose Ideas for Your Next Vineyard Photo Dump

💼 Affiliate Disclaimer:

Heads up, bestie! This post contains affiliate links. That means I may earn a small commission (at no extra cost to you) if you shop through the links I share. Thank you for supporting my iced coffee habit and keeping this glam train running.

She didn’t just step out—she floated into elegance. This look is giving sunset soirée in Santorini, and it’s dripping in quiet luxury. The off-the-shoulder cream top is soft, structured, and seriously sophisticated, letting those collarbones steal the spotlight. Paired with a flowy pleated cream midi skirt, she’s the definition of goddess energy—effortless movement, timeless silhouette, and pure elegance. On her feet? White strappy block-heel sandals that keep it polished but walkable (because champagne terraces have stairs, babe). She’s carrying a sleek champagne satin clutch that holds nothing but her lipstick, room key, and maybe a few hearts. Add in dainty gold studs and a soft curl that says “I woke up looking like this,” and this outfit becomes a masterclass in minimalist glamour.

She didn’t fly to the Amalfi Coast to not be the main character. This creamy monochrome look is what Italian It Girl energy is all about — timeless, minimal, and effortlessly rich.

🛍️ Shop the Look:

Oh she’s yacht-club royalty, darling—and she didn’t even have to name-drop to get the best table. This look is a masterclass in nautical chic. The oversized white button-down shirt is crisp, breezy, and perfectly undone, layered with a casually tied navy and white striped sweater over the shoulders—because yes, she’s that effortlessly polished. She pairs it with white tailored cuffed shorts that say “I summer in Saint-Tropez,” and finishes the look with a structured navy top-handle handbag that holds SPF, lip gloss, and a little bit of attitude. Her accessories? Chef’s kiss: tortoiseshell cat-eye sunglasses, gold hoop earrings, delicate layered necklaces, and a stack of gold bangles that clink like quiet luxury. This isn’t just an outfit—it’s an entire mood anchored in wealth, grace, and saltwater confidence.

If elegance had a uniform, this would be it. This crisp, clean look gives CEO on vacation, Vogue editor on a casual Friday, and yacht guest who RSVP’d ‘yes’ to everything. It’s proof that minimal is powerful when done right.

🛍️ Shop the Look:

Bonjour, fashion royalty. This look is serving Left Bank chic with a heavy pour of “don’t mess with me, I’m on my second espresso.” The blue-and-white striped button-down shirt is crisp, cool, and just a little bit undone for that effortless French-girl flair. Tucked into high-waisted cream pleated shorts, she’s channeling vintage Riviera elegance with modern flair. The tan leather belt cinches everything together like a pro, while that structured camel shoulder bag adds warmth and understated wealth. She tops it off with oversized black sunglasses (because eye contact is for amateurs), gold layered necklaces, and statement rings that look like heirlooms passed down from a trés chic grandmother. Basically, she didn’t come to sightsee—she came to set the style standard.

You know that one outfit that says “I have a trust fund, a publishing deal, and an espresso in hand”? Yeah, this is her. Whether you're in Paris or pretending you are, this crisp striped shirt + white short combo screams rich girl energy — minus the noise. Shop the look. Live the life.

🛍️ Shop the Look:

She’s giving “Capri-core” with a side of fresh air and fresher fashion. This breezy beauty is working a nude fitted tank top—sleek, seamless, and made for golden hour strolls. It’s tucked into high-waisted white tailored shorts that are crisp enough to say, “I packed light, but I packed smart.” Draped over her shoulders is a cozy beige knit sweater because she’s ready for sunset chills without sacrificing style. The tan leather belt snatches the waist and subtly elevates the whole fit. Toss in that elegant white crossbody bag with gold hardware, a pair of round sunglasses with tortoiseshell frames, and dainty gold jewelry, and voilà—this look is an effortless masterclass in quiet luxury.

She’s on a coastal path in Capri with espresso in hand and zero plans to check Slack. This outfit is what happens when minimalism goes on a luxury vacation. Chic, fresh, and effortlessly put together — it’s basically the soft launch of your rich-girl spring.
Shop the look and serve soft power all season long.

🛍️ Shop the Look:

Oh she’s not on vacation—she’s on a lifestyle tour. This outfit is preppy, polished, and serving “I summer in the Cyclades, and yes, I brought the yacht.” The navy zip-up polo shirt is classic with a twist—sporty, chic, and impossibly crisp. It’s tucked into high-waisted white tailored shorts that say “old money” but make it coastal. She finishes the look with white sneakers that are giving understated elegance, perfect for strutting seaside without breaking a sweat. That woven straw tote bag? Effortless. Spacious. Probably holding a Birkin-sized SPF. Top it off with black cat-eye sunglasses, a sleek gold watch, and mini hoop earrings, and you’ve got a look that’s equal parts Upper East Side and Mykonos cool.

She’s got 2% phone battery, 98% style. This look belongs at a harbor café with rosé and a Greek salad. It’s polished, breezy, and screams "I summer in three countries." A navy polo and tailored shorts are the ultimate quiet luxury combo that feels both crisp and casually commanding.

Shop the look and channel effortless elegance from deck to downtown.

🛍️ Shop the Look:

Ohhh, she's glowing like the Greek sun and dressed like she owns half the island. This is the ultimate "soft luxe meets Mediterranean magic" moment. The taupe ribbed tank top hugs just right—subtle, sculpted, and effortlessly elevated. It’s perfectly tucked into a pair of high-waisted white pleated shorts that are breezy, tailored, and rich in energy. She cinched it all together with a classic tan leather belt because details matter when you’re this polished. Add in those gold hoop earrings, a delicate chain bracelet, and the black and tortoise sunglasses casually in-hand, and you’ve got a look that whispers “old money” in a very expensive accent. Basically? She’s not chasing the summer—summer is chasing her.

This is your reminder that minimalist doesn’t mean boring. With crisp pleats, a body-hugging tank, and Santorini sunshine as your backdrop — you don’t need to try hard to look expensive. It’s giving rich, it's giving relaxed, and it’s absolutely giving main character energy.

Shop the Look & Pack Your Bags, Babe:

Power lunch in Positano? Don’t mind if she does. This look is giving “boardroom brain meets old-money beauty.” The navy fitted polo shirt keeps it clean, preppy, and just the right amount of polished, tucked perfectly into those high-waisted pleated cream trousers that mean business without breaking a sweat. She’s carrying a structured black designer handbag (you already know it screams “Don’t ask the price”), and holding a navy blazer like she might toss it on and close a deal before aperitivo hour. That black leather belt with gold hardware pulls the whole look together like a trust fund with style. Minimal? Yes. Monied? Absolutely. This outfit says, “I summer in the Amalfi Coast, but I still check my stocks at lunch.”

Channel your inner luxury consultant with this corporate-cool moment. Whether you’re leading meetings or leading with style, this navy-and-cream combo is the definition of ‘expensive taste meets minimal effort.’ Pair with gold hoops, a boss-babe bag, and a blazer that says “I own this building.”

Shop the Look That Closes Deals & Turns Heads:

She’s walking straight out of a yacht club fantasy and into La Dolce Vita, darling. This look is Mediterranean-chic with a side of "don’t call me, I’m on vacation." The oversized beige-and-white striped button-down shirt is equal parts breezy and bougie—half-tucked just right to show off that perfectly tailored white mini skirt. She finishes the look with white strappy heels that were made for strutting through seaside cafés (or away from drama). That structured white tote bag is big enough for SPF, a scarf, and secrets. And the final flourish? Oversized black cat-eye sunglasses—because she knows she’s the main event. Whether she’s boarding a boat or ordering a Bellini, this outfit is giving money, taste, and a one-way ticket to luxury.

This look screams “booked the yacht before brunch.” Perfect for your summer in Capri… or your weekend at the boardwalk. Master the rich-girl-on-vacation aesthetic with color blocking that’s classic, clean, and totally timeless.

Shop the Look to Live La Dolce Budget:

Oh honey, this look is Santorini CEO with a side of spritz. She's commanding cliffside views in a white double-breasted sleeveless blazer that’s sharper than your ex’s downfall, paired flawlessly with a matching white mini skirt that serves just enough leg without ever compromising class. The structured wicker handbag adds a dash of coastal vintage charm (because she packs light but lives luxe), while those angular black sunglasses deliver mystery and money. And don’t overlook the details: a sleek gold watch and that slicked-back bun? She's not on vacation—she's conducting board meetings from the balcony of a five-star villa. Minimal? Yes. Forgettable? Absolutely not.

This outfit didn’t come to play—it came to own the villa next door. Pairing structured tailoring with coastal softness, it’s the ultimate old money summer look. Add oversized sunglasses and a structured basket bag, and voilà—you’re fluent in “rich in Europe.”

🛍️ Shop the Look:

Oh, she’s not just sipping rosé—she’s sipping luxury, darling. This vineyard-ready slay is the definition of countryside chic. The crisp white button-down shirt is breezy, polished, and gives just enough undone energy to say, “Yes, I own a vineyard. No, you can’t sit with me.” She pairs it perfectly with high-waisted pleated khaki shorts that scream Old Money Vacation—those cuffed hems and that statement waistband? Iconic. Topping it all off is a wide-brim woven straw hat that blocks the sun and the drama. Add in gold chunky hoop earrings for just a whisper of glam, and this look is basically the style equivalent of a first-class upgrade. She’s not dressing for the wine tour—she is the main attraction.

Wine tasting, but make it fashion. This look is giving “casually sipping in Chianti while pretending I’m not checking Pinterest analytics.” Pair a crisp white shirt with soft tailored shorts, a straw hat, and a gold hoop moment—and you’ve got yourself a $13 outfit that looks like a $3,000 vacation.

🛍️ Shop the Look:

Yesss, this look is straight out of a Roman holiday fantasy—Audrey Hepburn could never! She’s turning heads and breaking hearts with that black high-neck tank top, a sleek, versatile staple every chic closet needs. The high-waisted wide-leg jeans are giving effortless cool, cinched at the waist with a bold statement belt that deserves its own moment. And let’s talk accessories: the blush crossbody bag with gold hardware is pure understated elegance, while the gold bangle bracelet and mini hoop earrings sprinkle in just the right amount of glam. This outfit says “I casually strolled into this café looking iconic,” and honestly? She did.

🛍️ Shop the Look:

Vespa-City Chic

💡 Pro tip: pair with a cold espresso and sunglasses that cost more than your rent (or just look like they do).

You made it to the bottom of the post—gold star, grape goddess. ✨ Whether you’re heading to Sonoma, Santorini, or just a wine bar that feels expensive, these fits guarantee you’ll look the part. Classy, effortless, a little bougie—but never boring.

Now go serve wine, serve looks, and serve main character energy.
And remember:
Your outfit should age like fine wine—flawlessly. 🍷😉

Ohhh, she’s giving boardroom meets brunch meets bold AF. This look is a power move with a playful twist, and I am here for it. The black tailored vest is sharp, structured, and slightly scandalous in the best way—buttoned up but definitely not boring. Paired with black wide-leg trousers, this set screams “CEO on the go” with a side of streetwear cool. And let’s talk about the plot twist: those red Adidas sneakers with white stripes? Chef’s kiss. They pop like an espresso shot in a sea of cold brew. The black crossbody bag is compact and classy, perfect for tossing in lip gloss, AirPods, and world domination plans. Topped off with oversized black sunglasses, she’s strutting through summer like it’s Fashion Week and every sidewalk is her runway. Casual. Chic. Completely unstoppable.

When old money minimalism collides with bold baddie energy, you get this look. It's sleek. It's smart. It's “I have meetings in Milan and sneakers in my carry-on” chic. The black vest and trousers whisper luxury, while the red sneakers shout confidence—and honestly? We’re listening. Whether you're power-walking to your next espresso or window-shopping in Rome, this outfit works overtime without trying too hard.

🛍️ Shop the Look

If modern Grace Kelly were sipping an oat milk latte under the Mediterranean sun, this would be her uniform. The taupe satin tube top hugs just right—smooth, sleek, and oh-so-luxurious without trying too hard. Paired with high-waisted white wide-leg trousers, this outfit says, “I brunch in silence and vacation in Santorini.” The structured tan mini tote is minimal perfection—sharp, clean lines that scream quiet luxury. Add in a dainty stack of gold bracelets, a gold pendant necklace, and those barely-there nude cat-eye sunglasses, and you’ve got an ensemble that whispers wealth with every breeze. It’s cool, confident, and completely curated for the woman who never breaks a sweat—even in 90-degree heat.

🛍️ Shop the Look:
Neutral Luxe Siren

  • Taupe Bandeau Top – Because tan lines are a choice, and this top is the main character

  • Wide-Leg White Trousers – Flowy, flattering, and screams “I don’t do polyester”

  • Structured Caramel Mini Tote – Clean lines and luxury vibes—she means business

  • Gold Chain Bracelet Stack – Not loud, but definitely noticed

  • Retro Narrow Sunglasses – Just dramatic enough to sip espresso and judge the gelato line

  • Soft Glam Waves + Golden Hour Glow – Styling tip: confidence is part of the look

Serving timeless elegance with a side of Mediterranean glam, this look is giving “I summer in Capri and I don’t check prices.” The sleeveless tan midi dress flows like a breeze and cinches perfectly at the waist with a chunky brown belt featuring a gold ring buckle—major rich aunt energy. She tops it off with oversized round sunglasses that say “don’t bother me unless it’s rosé or a yacht invite.” That structured tan tote bag? Big enough for beach reads, SPF, and receipts from all her enemies. And don’t get me started on the strappy block heel sandals—they’re neutral, elevated, and scream I walk cobblestone streets like they’re a runway. A stack of gold necklaces, a watch, and those effortless waves tie this look up in a bow made of chic confidence. Basically, if elegance were a summer outfit, this would be it.

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