What to Wear to a Winery Over 50

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Heading to wine country? Visiting a vineyard? Gurls, I’ve never been to Napa Valley, but Joe and I are considering a trip. He’s looking at hotels and travel arrangements, and I’m thinking about the important things, like what to wear! My research says comfy is key! And when isn’t it?

Here’s my take on what to wear to a winery over 50. For those of you who’ve been, leave a comment at the end and let me know what I’ve forgotten!

A First-Timer’s Guide to Winery Visits

Since this would be my first time, I did a little research on some common questions to help us both feel prepared.

  • Comfort is Key: You’ll likely be standing, walking on gravel paths, and possibly touring vineyards, so comfortable shoes are a non-negotiable.
  • Layer Up: Temperatures can vary from warm sun to a cool breeze in a cellar. A light jacket or cardigan is a smart addition.
  • Leave the Strong Scents at Home: Strong perfumes can interfere with the delicate aromas of wine, so it’s best to avoid them for a wine tasting.
  • What to Carry: A small handbag or crossbody is perfect for carrying your essentials without getting in the way.

Talbots Straight Ankle Cuff Jeans

I always start with a great pair of pants. I love that these crisp, Straight Ankle Jeans with a cuff hit just above the ankle, so I can show off my cute sandals. Made from stretch denim, they would be comfy during walks through the vines. Pair with a light blouse and I’m vineyard-ready. Lead me to the wine tasting experience!

  • Stretch denim adjusts as you move
  • Ankle cuff adds casual polish
  • Works with sandals or low wedges

Talbots Elbow Sleeve Shirt – Delicate Leopard

This Leopard Shirt would look good with the pants above! The leopard is classic but not loud, and the elbow sleeves would be super comfy for warm-weather sipping. The fabric looks like it drapes beautifully without clinging. I’d style it half-tucked into jeans for that laid-back-cool look, as I’m pretending that I love wine tastings. Ha!

  • Lightweight knit, easy to layer
  • Elbow sleeves are breezy and flattering
  • Soft leopard print adds a fun twist

Talbots Boot-Leg Pants – Refined Denim

If jeans feel too casual, these Boot-Leg Pants give that polished-to-dinner look with ease. Faux denim drapes elegantly, and they would look great with flats or sandals. No high heels on a wine tour! These are a step up, but still comfort-first.

  • Slim through hip, gentle flare at the bottom
  • Lightweight fabric won’t weigh you down
  • Ideal for vineyard dinners

Talbots Tie-Front Crewneck Tee – Camden Stripe

This Striped Tee is the definition of charming casual! The tie-front gives some shape, and the indigo stripes feel fresh and breathable. Perfect under a denim jacket for cooler cellar tours. It’s also available in a lovely yellow if you want something bolder.

  • Tie-front offers subtle waist definition
  • Soft knit with casual-chic appeal
  • Pairs beautifully with jeans or pants

Ann Taylor Belted Wide-Leg Linen-Blend Pant

I also think these would be gorgeous and appropriate. Maybe for upscale tastings. I don’t want to drag the hem through the dirt while picking grapes, lol. These Linen-Blend Wide Leg Pants are it. They flow beautifully through vineyard terraces, and the belted waist flatters and defines. Great with sandals or wedges. Just make sure to pack comfortable shoes with all of these outfits!

  • Linen blend is breathable and cool
  • Wide-leg silhouette is effortlessly chic
  • Belt pulls your look together

Chico’s Frayed Denim Maxi Dress

Tania is wearing a frayed denim dress in front of a couch on a porch
Chico’s Frayed Denim Maxi Dress

Love how this Denim Maxi Dress keeps it classic casual but with a stylish edge. The frayed hem adds texture, and I could wear it belted or loose. I’ve got a hundred lightweight sweaters I could throw on with this, too, for a cooler day of wine tasting. Add your favorite sandals and a straw hat for complete winery style.

  • Maxi length is flowy yet grounded
  • Frayed detail offers a relaxed look
  • Easy to dress up with accessories

What to Pack

All of my research said to remember sun protection. Apparently, winery sun can surprise you. But there are a few other things you should remember.

Talbots Packable Straw Hat

All of my research said to remember sun protection. Apparently, winery sun can surprise you. This Packable Straw Hat is practical and chic.

  • Folds flat and holds shape
  • Wide brim offers sun protection
  • Adds those final summer-vacay vibes

Women’s Arch Support Sandals Adjustable Thong

Comfortable sandals with arch support? Yes, please! These Adjustable Thongs let your feet breathe, would handle cobblestones, and look good with everything I’ve linked above. Perfect for standing through a tour or picnic.

  • Adjustable straps for a perfect fit
  • Arch support saves your feet
  • Lightweight and go-with-everything style

Vionic Uptown Willa Slip-On Sneaker

These Slip-On Sneakers are dressier than your basic kicks, but are still built for comfort. Ideal for gravel paths, winding winery walks, or lifting your weekend strolling vibes. They go with almost every winery outfit!

  • Built-in arch support
  • Slip-on yet polished enough for casual dress
  • Subtle suede gives grown-up texture

Winery Style Is A Blend Between Fashion and Function

Winery style over 50? I’m thinking it’s all about the blend: comfort underfoot, breathable layers, and relaxed silhouettes that move with you. Wear a sundress, a skirt, or even your favorite boots if the weather is cooler. Whatever attire you choose, just wear it with confidence. Cheers to that!

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John 3:17 (NIV)
17 For God did not send his Son into the world to condemn the world, but to save the world through him.

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72 Comments

  1. that denim dress is UGLY