Chic Wine Tasting Outfits: 15 Stylish Ideas to Try

Updated: 07 Jul 2025

Planning a trip to a vineyard or wine tasting event and wondering what to wear? Whether you’re headed to Napa Valley, a countryside estate, or a cozy local wine bar, your outfit should strike the perfect balance between comfort, elegance, and Instagram-worthy flair.

In this guide, we’ll walk you through stylish wine tasting outfit ideas for every season, including casual day trips, upscale tastings, and romantic vineyard getaways. From flowy dresses and wide-brim hats to smart layers and statement shoes, discover how to sip in style without sacrificing comfort.

1. The Flowy Midi Dress & Wedges Combo (Spring Classic)

A flowy midi dress is a timeless wine tasting staple. Choose a floral or pastel print for spring to complement the blooming vineyard surroundings. Pair it with espadrille wedges—they’re chic and vineyard-friendly (no sinking into the soil). Add a straw crossbody and oversized sunglasses to complete the look.

Style Tip: Go for breathable fabrics like cotton or chiffon to stay comfortable in warmer spring temps.

2. Monochrome Jumpsuit & Statement Earrings (Modern Elegance)

Want a sleek and fuss-free ensemble? A monochrome jumpsuit in neutral tones (think ivory, olive, or rust) offers both comfort and sophistication. Cinch the waist with a belt and add statement earrings for a touch of glam. This look is ideal for urban wine bars or modern tasting lounges.

Bonus: Jumpsuits allow easy mobility for vineyard tours and tastings alike.

3. Maxi Skirt & Knotted Blouse (Boho-Chic Vibes)

Channel relaxed bohemian flair with a printed maxi skirt and a tied-at-the-waist blouse. Earthy tones or jewel shades elevate the look. Add a wide-brim hat and stacked bangles to play up the boho aesthetic.

Perfect For: Fall vineyard tours or artfully curated boutique wineries.

4. Tailored Shorts & Linen Blazer (Summer Sophistication)

Hot weather doesn’t mean you need to sacrifice polish. Opt for high-waisted tailored shorts and a lightweight linen blazer over a tank or bralette top. Finish with strappy sandals and a structured mini bag.

Style Hack: Choose earthy or muted tones like beige, khaki, or sage for a refined color palette.

5. Wrap Dress & Straw Hat (Timeless Romance)

A wrap dress flatters every figure and moves gracefully as you stroll through vineyards. Opt for light hues or subtle prints. A straw hat not only adds flair but protects you from the sun.

Ideal For: Day-to-evening tastings or romantic vineyard dates.

6. Dark Skinny Jeans & Off-Shoulder Top (Casual Cool)

If dresses aren’t your thing, skinny jeans paired with an off-the-shoulder blouse offer a relaxed yet feminine touch. Choose dark-wash jeans and flowy, breathable fabrics. Add ankle boots or low block heels to elevate the outfit.

Versatile Choice: Great for both indoor tastings and outdoor wine picnics.

7. Matching Two-Piece Set (Effortlessly Put Together)

Coordinated sets take the guesswork out of styling. A flowy two-piece with a crop top and matching skirt or wide-leg pants delivers maximum style with minimal effort.

Style Highlight: Great for Insta-worthy photos and transitions well into evening events.

8. Midi Skirt & Denim Jacket (Layered for Fall)

Wine tastings in autumn call for layered sophistication. Pair a knit or corduroy midi skirt with a fitted top and cropped denim jacket. Add tights and ankle boots if temperatures drop.

Extra Touch: Choose a felt fedora or plaid scarf for a cozy seasonal accent.

9. Knit Dress & Knee-High Boots (Cozy Chic)

For chillier days, a ribbed knit dress paired with knee-high boots is a polished yet warm option. Add a belt to define your waist and a crossbody bag to keep things hands-free.

Ideal For: Cozy countryside wine tastings or late-fall excursions.

10. White Blouse & Wide-Leg Trousers (Minimalist Chic)

You can never go wrong with a crisp white blouse tucked into high-waisted wide-leg trousers. This look screams sophistication and is comfortable enough for a full day of sipping and walking.

Style Finish: Add a bold lip color or gold accessories to elevate the simplicity.

11. Floral Sundress & Flat Sandals (Laid-Back Charm)

If the weather’s warm and the vibe is casual, a breezy sundress and flat sandals are a go-to combo. Look for dainty floral prints and breathable fabrics like rayon or cotton.

Instagram-Ready Tip: A mini crossbody and layered gold necklaces add polish without feeling overdone.

12. Utility Romper & Sunglasses (Safari-Inspired Cool)

A structured utility romper brings a touch of edge to your vineyard look. Olive green, khaki, or tan shades blend perfectly with rustic settings. Pair with platform sandals and oversized sunglasses for a modern twist.

Perfect For: Outdoor wine tasting adventures or vineyard tours with photo ops.

13. Turtleneck & Plaid Skirt (Winter Winery Look)

Cold weather wine tasting? Go for a fitted turtleneck tucked into a plaid skirt with tights and ankle boots. Top it off with a belted wool coat or a longline trench.

Warmth + Style: Layer with a scarf and leather gloves for bonus elegance and coziness.

14. Silk Camisole & Cardigan (Layered Luxury)

Layer a silky camisole under a chunky cardigan for a textured, transitional look. Pair with cropped jeans or a satin midi skirt and heeled booties. This combo is feminine and weather-versatile.

Great For: Late spring or early fall tastings where weather shifts throughout the day.

15. Little Black Dress (Always a Win)

When in doubt, an LBD never fails. Choose one with delicate straps, ruffled sleeves, or a sweetheart neckline for a wine-country twist. Pair with wedges or kitten heels and add a colorful clutch.

Timeless Appeal: Dress it up or down depending on the venue.

Tips for Styling Wine Tasting Outfits

1. Comfort is Key:
You’ll likely be walking, standing, and possibly touring the vineyard. Avoid tight shoes or anything too restricting.

2. Know the Venue:
An upscale Napa estate may call for a different look than a rustic countryside winery. Do a little research in advance.

3. Weather Matters:
Layers work wonders to bring a cardigan, scarf, or light jacket depending on the season. A sudden breeze in a vineyard can change everything!

4. Accessories Make the Look:
Hats, sunglasses, jewelry, and structured bags elevate any basic outfit. Just don’t over-accessorize comfort is still top priority.

5. Shoes to Avoid:
Say no to stilettos and narrow heels, they’ll sink into the grass or make walking on cobblestone paths difficult. Opt for wedges, block heels, boots, or stylish flats.

Bonus: What Not to Wear on a Wine Tasting Trip

Overly tight or restrictive clothing: You want to enjoy wine, not worry about adjusting your outfit all day.
Flashy logos or loud branding: Wine country is about understated luxury and relaxed elegance.
Uncomfortable heels: No one wants sore feet after vineyard hopping.
All white: Spills happen unless you’re extremely cautious, opt for patterned or darker tones.

Your Outfit Sets the Tone

Wine tasting isn’t just about the wine, it’s about the entire experience. Your outfit should reflect the occasion: elegant yet approachable, stylish yet comfortable. Whether you’re basking in the sun at a Tuscan-style estate or sipping a bold red at a rustic barn winery, your wardrobe can enhance the moment.

Remember: when you feel confident, you look effortlessly chic. So pour that glass, pose by the vines, and sip in style.