You booked the winery tour. You lined up your tasting flight. Now you’re staring at your closet wondering what “chic but chill” actually looks like.

Honestly, I’ve stood in that same doorway thinking, do I dress cute-casual or full vineyard goddess? If you’re asking the same question, you’re in the perfect place.

I’ve messed around with enough winery outfits to admit this: you need comfort, style, and shoes that won’t make you cry walking on gravel.

Ever tried heels and regretted every step? Same. So I rounded up 24 winery tour outfit ideas that nail the vibe without trying too hard.

I’ll share some personal opinions, tiny anecdotes, and outfits that carried me through vineyard photos, too much cheese, and at least one questionable rosé.

Let’s build the winery wardrobe of your dreams.

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1. Breezy Linen Dress

I love linen because it looks elevated without effort. You move, it flows. You sit, it still looks elegant.
Key perks:

• Breathable
• Stylishly minimal
• Great for hot days

Ever notice how linen turns every photo into a magazine moment?

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2. White Blouse + High-Waist Jeans

You throw on a crisp blouse, tuck it into denim, and boom—you look like you know what tannins are.
Choose structured jeans for a clean silhouette.

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3. Midi Skirt + Strappy Tank

A midi skirt gives you easy movement while still looking polished.
Strappy tanks balance the look without overthinking it.

I wore this combo once, and someone asked if I worked at the vineyard. I didn’t know whether to be flattered or terrified.

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4. Casual Jumpsuit

A jumpsuit saves time and stress.
It works with:

• Denim jackets
• Sandals
• Crossbody bags

No struggling to match separates.

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5. Wrap Dress + Block Heels

A wrap dress flatters everything and works in every season.
Grab block heels so you don’t sink into grass. You’ll thank me.

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6. Blazer + Straight-Leg Denim

This feels smart without being stiff.
Add a silk tank for a soft contrast.

Ask yourself: Why does a blazer fix everything?

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7. Floral Dress With Sandals

You can never go wrong with florals at a winery.
You look like you belong among grapes.

Pro tip: Pick subtle floral patterns for more polish.

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8. Matching Set

Matching sets make you look put together automatically.
I love them because you get max style with minimal energy.

You can mix and match pieces later. FYI, that makes your wallet very happy.

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9. Knit Dress + Boots

This look screams fall winery vibes.
It keeps you cozy without feeling bulky.

Try suede boots to complement the softness.

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10. Wide-Leg Pants + Fitted Top

Wide-leg pants feel relaxed and chic.
Pair with a fitted top to balance proportions.

IMO, this combo gives instant elegance.

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11. Ribbed Tank + Full Skirt

A fitted ribbed tank keeps things simple.
A full skirt adds movement and personality.

This alone convinces anyone you have good taste.

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12. Button-Down Shirt Dress

A shirt dress makes you look clean, polished, and comfortable.
You can belt it for more shape.

I wore one last summer, and it kept me cool even when the wine didn’t.

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13. Sweater + Slip Skirt

This combo gives casual luxury vibes.
You stay comfy while looking like you belong in a vineyard commercial.

Bold takeaway: Slip skirts pair with literally everything.

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14. Cropped Sweater + High-Waist Jeans

This look blends cozy and cute.
Pick jeans with structure so the outfit doesn’t feel sloppy.

I like French-tucking the sweater for extra shape.

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15. Light Cardigan + Sundress

A cardigan dresses down a sundress just enough for chill winery vibes.
Perfect for breezy evenings.

Want that casual layered look without trying? This is it.

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16. Utility Jacket + Midi Dress

A utility jacket keeps things grounded.
The mix of structured outerwear with a flowing dress hits the sweet spot.

You can sip red wine and look cool doing it.

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17. Denim Dress

A denim dress gives laid-back polish.
It works with sneakers or sandals easily.

It’s also comfortable enough for long tours.

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18. Silk Blouse + Trousers

A silk blouse feels luxe.
Trousers polish the look without feeling stuffy.

Ever wonder how to dress “grown” without age yourself? This.

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19. Monochrome Set

Wear one color head-to-toe for immediate sophistication.
Go neutral for the cleanest look.

This never fails on photos, trust me.

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20. Turtleneck + Midi Skirt

A turtleneck keeps things sleek.
A midi skirt adds graceful movement.

I love this for cooler winery tastings.

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21. Breezy Romper

Cute, functional, and perfect for warm days.
Pair with sandals or low wedges.

Great pics guaranteed.

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22. Slip Dress + Denim Jacket

This combo balances sexy and relaxed.
Throw on a denim jacket to bring the outfit down to earth.

You never look overdressed with this.

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23. Long Vest + Jeans

A long vest adds instant structure.
Pair with jeans and a tank for effortless photos.

I like this outfit because it looks chic from every angle.

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24. Classic White Tee + Linen Pants

The classics never lie.
A crisp tee and linen pants feel fresh and relaxed.

This gives subtle vacation energy, even if you’re not on one. 🙂

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Extra Style Tips for Winery Tours

You want function and fashion.
Let’s keep things grounded with real advice.

Footwear Matters

Vineyards often mean gravel, grass, and uneven surfaces.
Heels love to sink, so ditch stilettos unless you enjoy suffering.

Best shoe options:

• Flat sandals
• Block heels
• Low wedges
• Sneakers

Bold truth: Comfort always wins.

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Accessories That Add Polish

You can elevate simple outfits with curated accessories.

• Straw hats
• Sunglasses
• Layered necklaces
• Crossbody bags

Keep it understated.
The wine already brings drama.

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Think About Weather

Winery tours can last hours.
Prep for shifting temps.

• Bring a lightweight layer
• Wear breathable fabrics
• Pack a mini umbrella if needed

You’ll thank yourself when the breeze hits.

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Colors That Work Best

Neutrals complement the natural setting.
Think:

• Cream
• Olive
• Denim blue
• Burgundy

Bright colors look striking too, but neutrals always win for that soft vineyard vibe.

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Patterns for Winery Fits

If you love prints, go for subtle ones.
Big prints can overpower the scenery.

Try:

• Small florals
• Gingham
• Tiny dots

These add interest without distraction.

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Bags That Make Sense

You’ll want free hands for holding all that wine.
Crossbody bags win every time.

Look for:

• Adjustable straps
• Secure closures
• Enough room for essentials

No one needs tote-bag chaos mid-tasting.

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Seasonal Winery Outfit Ideas

Sometimes the season matters more than the outfit.

Spring

• Linen dresses
• Light layers
• Breezy pants

Summer

• Sundresses
• Sandals
• Straw hats

Fall

• Knit dresses
• Boots
• Warm tones

Winter

• Turtlenecks
• Coats
• Cashmere scarf

Cool weather calls for wine by the fire. Yes, please.

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Final Thoughts

Winery tours offer the perfect excuse to dress cute, sip good wine, and take questionable photos you’ll overanalyze later. The best outfits balance comfort and style while letting you enjoy the day. You don’t need an entirely new wardrobe. You just need smart pieces that work with your vibe.

I love outfits that let me taste, walk, chat, and sink into a hammock without feeling squeezed or overheated. You want classic pieces that make you feel confident in every photo—and every sip.