The Perfect Summer Wine Tasting Outfits to Try Now

There are a few summer activities that I absolutely live for—catching a baseball game, having a picnic in Central Park—but there’s one that tops them all: wine tasting. Whether it’s a bachelorette weekend or just an excuse to round up my college girlfriends, there’s nothing better than being outside, laughing way too loud, and sipping a cold glass of wine. Call me basic if you want—honestly, I’d agree. And let’s be honest, half the fun is planning the perfect summer wine tasting outfits to match the vibe.

This post is all about summer wine tasting outfits.

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But let’s be real: my favorite part of wine-tasting experience? Planning the perfect outfit. I love getting dressed for a vineyard day. And during the summer months, it’s all about nailing a specific aesthetic.

Do I go full-on style icon with high heels and a flirty dress? Or keep it laid-back with linen shorts and a wide-brimmed hat? The options are endless, and honestly, I get so much joy out of curating a look that’s both cute and functional—because let’s be real, walking across uneven terrain in stilettos is a bold move I’m not always ready to make.

What to Wear Wine Tasting

Whether I’m dressing in breathable fabrics or leaning into wine country casual with comfortable shoes, every outfit choice is just another way I get to express my personal style.

And since I can’t justify visiting twelve wineries this summer (that might be… irresponsible… or would it?!) I’m dropping all my go-to summer wine tasting outfits here. These are the ones I’ve either worn, saved, or mentally styled while pretending I don’t have three tabs open for Napa Valley flights.

12+ Outfit Ideas for the Perfect Day of Wine Tasting

1. High Heels & Flowy Dress

Okay, so I know high heels at a winery sounds risky—but hear me out. If it’s more of a sit-and-sip type of spot, a block heel and a floaty dress are chef’s kiss. It makes me feel like the main character, especially if I throw on a red lip and big sunnies.

2. Flat Sandals & Maxi Dress

When I know I’ll be walking a lot or going on a full winery tour, flat shoes are a must. A flowy maxi dress in colorful tones or neutral colors, paired with a comfy sandal, is a great choice. Plus, it’s a good idea for warm days when you want to look cute and stay cool.

3. Light Jacket & Summer Dress

I always forget how quickly the temps drop once the sun dips behind the vines. A light cardigan or jacket layered over a strappy dress is always a good option—especially if you’re hitting up any wine cellars. It adds a touch of elegance while keeping things casual.

4. Denim Jacket & All White Outfit

I’m obsessed with all white outfits during the late spring and summer. I’ll throw on a crisp white dress or linen set with a slightly oversized denim jacket—it’s a chic look that gives off J.Crew catalogue meets Napa Valley energy. Just maybe steer clear of reds unless you’re okay living on the edge.

5. Wide-Brimmed Hat & Button-Down Shirt

This combo is a total wine lover’s fantasy. I half-tuck a button-down shirt (linen or cotton, always) into white shorts, throw on a sun hat for both sun protection and style, and suddenly I feel like I’m starring in a Nancy Meyers romcom. It’s cute, comfy, and clutch for those midday tastings under the summer sun.

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6. White Dress & Bright Comfortable Flats

A white mini or midi dress is basically my perfect choice for any winery experience. I like to pair it with comfortable flats in a trendy shade like ballet pink or cherry red—it adds that fun pop of color while keeping things practical. It’s also a great option for those who want a little drama without the heel hassle.

7. Ankle Boots & Floral Dress

This combo is my answer to cooler months or rustic vineyards with gravel. A sweet floral-patterned dress and ankle boots strike that balance between soft and structured. It’s ideal for spots with uneven terrain, and you can always swap in longer pants or a leather jacket if it’s chillier.

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8. Summer Dresses & Pop of Color Accessory

One of the important things I’ve learned? A simple dress gets instantly elevated with a bright bag or shoes. Think colorful small handbags, cherry red earrings, or neon sandals. This is also the time of year to have fun with bright colors—you’re outside, it’s sunny, go bold!

9. Maxi Dress & Stylish Scarf

Nothing screams “wine weekend” like a scarf in your hair or tied to your crossbody bag. I did this once with a rust-colored maxi dress and got compliments all day. It’s such an easy way to add that extra touch of elegance without overthinking it.

10. Button-Down Shirt & Pair of Jeans

A classic for a reason. This is a casual look I lean on for cooler temperatures or more relaxed winery settings. I go with a crisp front button closure shirt tucked into high-waisted jeans and pair of mules or ballet flats. Add a slick bun and gold hoops—done.

11. Handheld Purse & Summer Dress

Tiny handheld purses are impractical in the best way. I know I can’t fit much in them, but I never regret bringing one when I’m in a cute sundress. They’re perfect for holding the last thing—lip gloss, card, and keys—and they photograph so well with a glass of rosé.

12. White Linen Set & Knee-High Boots

This combo is my go-to when the weather’s in that weird in-between—late summer slipping into the colder months. A crisp white linen set keeps things fresh and breathable, while knee-high boots add just enough edge (and warmth). Top it off with a western-style cowboy hat, and suddenly you’re giving cool-girl vineyard rodeo—unexpected, but it works.

13. Comfortable Flats & Pair of Jeans

On the days I want to keep it super simple, I go with jeans, a tank, and comfortable shoes. It’s a great way to look put-together while still being able to walk around, lounge, and focus on the important stuff—aka wine.

Cheers to the Perfect Summer Wine Tasting Outfits

If there’s one thing wine lovers know, it’s that the right outfit can turn a good time into a great one. Whether you’re headed to a casual vineyard picnic or something a little more elevated, the winery dress code can go either way—so it’s smart to be prepared.

I like to keep a few backup ideas in the mix, like one of my go-to cocktail dresses that works for an impromptu wine tasting reservation or a dressier tasting room. Toss on some gold hoops, grab a small handbag (just big enough for your phone, card, and lip gloss), and you’ve got the perfect way to sip in style.

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