If you’re planning a special outing to discover a new favourite winery, after you choose where to go, you need to decide what to wear! Choosing the right outfit for a winery visit is more than just a matter of aesthetics; it plays a significant role in enhancing your overall experience. Comfort should be a top priority, as you'll be spending a considerable amount of time strolling through vineyards, sampling wines, and enjoying the ambience. At the same time, style and practicality shouldn't be compromised, as wineries often have a certain charm and elegance - and possibly a dress code - that can inspire your sartorial choices. By carefully selecting your winter wine tour outfits, you can strike the perfect balance between looking fashionable and feeling relaxed throughout the day.

In this guide, we'll share some of our best advice and suggestions for how to dress comfortably and attractively for your much-anticipated winter wine tour. We'll explore  wardrobe options that mix warmth, refinement, and versatility. This means everything from layering strategies and suitable footwear to accessories that lend a touch of flair. So, whether you're a seasoned wine aficionado or a first-time winery visitor, prepare to take your winter wine tour attire to new levels of comfort and fashion.

What to Wear to a Winery: Outfit Inspiration

Featuring Our Leopard Cardi - Tan

Wineries automatically inspire a certain elegance, so choosing the right outfit can help elevate your experience. Is your wardrobe winery-ready? We've come up with some outfit inspiration that strikes the perfect balance between comfort, weather adaptability, and impeccable style. Perfect for exploring vineyards, savouring delicious blends, or simply enjoying the picturesque ambiance, these ensembles will ensure you feel confident and fabulous.

  • Timeless Elegance. Embrace a touch of tradition with a dress and cardigan combo. Opt for a flowy midi dress in a rich jewel tone or a classic floral print to add a romantic allure. Pair it with a cosy, chunky-knit cardigan that compliments the colour palette of your dress. Complete the look with ankle boots or knee-high boots for a chic and polished appearance. This OOTD exudes sophistication while keeping you warm and comfortable during your winter wine tour.
  • Casual Chic. Put together a chic and laid-back look by pairing trendy tops with slacks or denim. Choose a pair of dark washed or neutral-coloured tailored pants that fit you well, and pair with a chic top or a lightweight sweater. Scarves and statement necklaces are great ways to add a splash of colour or design to your outfit. Finish the outfit off with some ankle boots or loafers, both of which are practical and fashionable for exploring. This is a wonderful combination of relaxed ease and refined simplicity.
  • Flirty and Fun. Embrace the feminine side of winery fashion with a skirt and top combination. Choose a flared or pleated skirt in a fun print like flowers or polka dots. Depending on the temperature, pair it with a fitted shirt or a cosy sweater. Add a fashionable belt to the set to define your waistline and add a touch of charm. For a comfy and stylish look, pair with ballet flats or low-heeled boots. You’ll feel like an elegant muse amidst the scenic winery landscapes.

Remember, accessories are the secret ingredient to elevate any outfit. Consider adding a wide-brimmed hat, oversized sunglasses, delicate jewellery, or a trendy belt bag to enhance your ensemble. 

Regardless of the outfit you choose, make comfort as the foundation of your winery attire. Select breathable fabrics that allow you to move freely and regulate your body temperature. Layering is key for cooler temperatures, so have a stylish cardigan or wrap on hand for extra warmth. And don't forget to wear comfortable shoes suitable for walking on various terrains.

With these inspiring winter wine tour outfits, you're well-equipped to dress confidently and stylishly. So, prepare to sip, swirl, and savour in style as you embark on an unforgettable winery experience. 

Daytime Winery Outfits

Featuring Our Rayon Overall - Olive

When it comes to daytime winery outings, comfort and style go hand in hand. Here is some fashion inspiration to help you manage your midday winery adventures with ease.

  • When it comes to daytime winery wear, light colours take front stage. They not only reflect the sun's rays, keeping you cool, but they also emanate a fresh and polished look that complements the vineyards' natural beauty. Consider using a palette of white, beige, cream, or pastel colours and mixing them for an eye-catching contrast.
  • Prioritise loose-fitting attire that allows you to move freely and enjoy the day without feeling constricted for maximum comfort. Flowy blouses, wide-leg slacks, and shorts are excellent choices. Choose breathable fabrics and bring along a shrug or cardigan in case you need a bit of warming up.
  • Comfortable footwear is an absolute must for any daytime winery outfit. Leave the heels at home and opt for flats, sandals, sneakers, or boots that effortlessly mix style and functionality. Prioritise shoes that provide adequate support and are appropriate for walking on a variety of terrains. Don't forget to accessorise with a hat, sunglasses, or a lightweight scarf to shield yourself from the sun while also adding a personal touch to your ensemble.

Now, let's talk about a standout piece for your daytime winery adventures – our Rayon Overall. Crafted from soft and breathable fabric, these overalls drape beautifully on your body, ensuring all-day comfort. Available in a range of light colours, these overalls perfectly complement the winery ambiance. Finish the look when you wear a simple tee or tank top underneath, and don’t forget to accessorise!

Evening Winery Outfits

Featuring Our Izzy Dress - Black

When the sun sets and the winery ambiance takes on a more enchanting glow, it's time to embrace the allure of evening events or romantic date nights. Here are three winter wine tour outfits to inspire your evening winery look.

  • Floral Jumpsuit. Make an impression in a floral jumpsuit, which mixes ease and style. The whimsical floral pattern will liven up any outfit. Wearing a kitten heel or wedges, a chic purse, and well-curated jewellery will round out the ensemble.
  • Chic Dress. This is a timeless choice for evening winery events, seamlessly transitioning from day to night. Embrace the versatility of a classic black dress or express your personality with a pop of colour or a captivating print. 
  • Dressy Separates. For ladies who prefer to mix and match, dressy separates offer endless possibilities for creating your own winery outfit. Dress up a skirt or tailored pants with a chic blouse or cosy sweater, depending on the season and the event. Use fabrics and textures that contrast one another to create visual interest. Add sophistication and comfort by layering a blazer or cardigan over your outfit. 

When selecting your evening winery outfit, don’t forget to inquire about the venue's dress code and the level of formality of the event. Some wineries have a more relaxed atmosphere so casual chic outfits will do, while others may require something more formal.

Accessories and Finishing Touches

Featuring Our Stripe Scarf - Beige/Cream

To truly amp up your winter wine tour outfits, it's all about the finishing touches. These small but impactful details have the power to transform your look from ordinary to extraordinary. Let's explore the significance of accessories in completing your winery outfits.

  • Start with head-turning accessories. Consider a stylish straw hat for a touch of charm and to protect you from the sun's rays as you stroll through the vineyards. Pair it with fashionable sunnies for an air of glamour. 
  • Statement earrings are another must-have accessory. Choose bold, eye-catching designs that add a touch of elegance and drama to your ensemble. Whether you opt for intricate metallic pieces, vibrant gemstone accents, or bohemian-inspired tassels, statement earrings are sure to make a stylish impact.
  • When it comes to handbags, consider a woven or straw option that exudes a rustic charm, perfectly complementing the winery setting. Not only are they on-trend, but they also provide ample space for your essentials while adding a touch of textural interest to your outfit. Choose a style that suits your personal taste, whether it's a small crossbody bag or a roomy tote.
  • Footwear is a crucial element that should not be overlooked. Opt for comfortable yet stylish options such as sandals, wedges, or stylish flats. These choices will let you focus on the vineyard and not your aching feet. Look for designs that offer support and stability while reflecting your personal style.

Do’s and Don’ts of Winery Outfits

Here are general guidelines that will make sure your outfit is winery-ready. Adapt them to suit your personal preferences and the specific winery setting. 


  • Opt for lightweight and breathable fabrics that you can layer with a jacket or cardigan.
  • Consider flowy dresses, maxi dresses, or skirts for a feminine and stylish look.
Featuring Our Fresia Dress - Floral

  • Choose comfortable footwear like wedges, sandals, or flats. 
  • Accessorise with hats, sunglasses, statement earrings, or woven handbags. 
Featuring Our Gemma Necklace - Silver

  • Dress according to the winery's dress code or guidelines.
  • Do check the weather forecast and dress accordingly for comfort throughout the day.


  • Don’t choose tight-fitting or restrictive clothing that restricts movement or comfort.
  • Don’t overdo the accessories or jewellery, as it’s impractical for this setting.
  • Don’t wear strong perfumes or fragrances that may interfere with the wine-tasting experience.
  • Don’t wear open-toed shoes or sandals in cold or wet weather conditions.

Flaunt Your Style With Freez

Now you should have the confidence to visit any winery in style and comfort, so you can focus on the experience, not your wardrobe choices. With so many options, you’ll surely let your personality shine as you dress to tour!

At Freez, we want to help you create chic winery outfits. We offer a range of affordable, stylish options to suit your taste and budget. Explore our latest arrivals to discover the hottest winter wine tour outfits that will make you feel like a fashion icon. With us by your side, you can confidently tour the vineyards while creating unforgettable memories. So, gear up, browse our new arrivals, and unlock your winery fashion journey.

July 21, 2023 — Freez Clothing