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What to wear to a winery: The all-seasons guide for men

How to dress for a winery any time of year

Man drinking wine in a chair
Mario Ame / Unsplash

Whether you’re taking a road trip or visiting for an event, wineries are excellent places to enjoy nature and have some tasty wine. However, unlike other places like the golf course or the office, picking an outfit for the winery can be slightly more challenging. This challenge comes from the fact that wineries are meant to be slightly more upscale locations, but they aren’t entirely formal affairs. Certain rules and expectations come with visiting a winery and are largely influenced by the season you visit them in.

No matter when you visit your next winery, you want to keep in mind the location, weather, and event before picking out your next look. You want to choose a look casual enough to be comfortable in the elements while still dressy enough to look sophisticated and elegant. Keep reading to find out what to wear to a winery.

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Summer winery outfit guide

Men walking in a winery
Nice M Nshuti / Unsplash

The key to your winery look in any weather is balancing between elegant and casual. In the summer, you also want to choose clothes that will keep you cool, even in the warmest weather. Short-sleeved polos and button-downs are two simple options that strike this balance with ease. Always avoid graphic T-shirts or loud prints that distract from the overall aesthetic. A simple T-shirt can work as long as it fits well and is in a solid color. 

For bottoms, you’ll want to stick with well-fitting pieces that are easy to walk in. Depending on the location of the winery, you can get away with high-quality denim, especially if you’ll be walking through the vineyards. If you plan to stay around the wine-tasting area, you can also opt for linen pants for a lightweight option that’s still sophisticated. Shorts are also permissible, so long they are in neutral hues like tan, white, or black. Avoid baggy bottoms and ill-fitting pants that seem out of place. Stick to tailored bottoms for an easy styling option that works well with any top. 

Although the summer weather typically means it’s time to wear sandals, a winery isn’t a place to wear your favorite flip-flops. Stick to closed-toe shoes so you can comfortably walk around rough terrain, but avoid running shoes or sneakers. Slip-on shoes or leather walking shoes are two comfortable options that are casual yet elegant. For those extra sunny days, you can add a pair of black sunglasses to help block out the sun’s rays and help bring your look together. 

Fall winery outfit guide

Man wearing a yellow sweater drinking wine
cottonbro studio / Pexels

Heading to a winery in the fall season is always a good idea. As the leaves start falling and the weather begins cooling down, there’s no better cozy activity than heading to a winery. During these slightly chilly months, you’ll want to make adjustments to help bare the weather better. If you’re concerned about feeling the cold weather later on in the day, you’ll want to opt for a long-sleeve polo or button-down top that will still give you this elegant casual mixture without leaving you open to the elements. Another option is a simple cashmere sweater that you can wear with any solid-colored bottom. Add a collared button-down underneath for a layered look, or opt for just a sweater look. 

The fall season is the best time to hang up your shorts and opt for dress slacks. No need to wear your formal suit pants, but neutral-colored dress trousers are a great styling pair that makes it easy to wear with any top. Try darker neutrals like black or navy blue for a more fall-inspired outfit.

Regardless of the weather, your shoes should be a balance of dressy and casual. However, when the weather starts cooling down, it can be a good time to bring out your favorite leather lace-up boots. Ensure your boots aren’t too bulky or rough looking to avoid clashing with the rest of your look. It’s not unusual for fall weather to turn cold at a moment’s notice, meaning it’s always a good idea to come prepared with a scarf to help aid against the weather. Stick with sleek scarves like cashmere or fine wool for a more upscale addition. 

Winter winery outfit guide

Man standing in a winery in blazer
cottonbro studios / Pexels

Depending on where you live, winter can mean wearing plenty of layers to the winery to help withstand the cold. Whether it’s just cold or snowing, you want to be prepared for any situation. Following the typical fall outfit, you’ll want to add a few outer layers to your look to help keep you warm. If you plan to wear a sweater alone, try pairing it with a wool blazer. Not only will this add some texture to your look, but add another warm layer. You can also add a thick blazer to your layered sweater and collared button-down outfit for even more warmth. Your blazer also lets you experiment with patterns and textures, such as with a corduroy material or plaid pattern. Keep any pattern minimal and avoid any over-the-top print. 

Keep your bottoms minimal to help offset the heavier top picks, and to help keep you mobile throughout the day. If the weather is extreme, you may want to add thermal pants underneath; however, this is entirely influenced by the weather. 

Since winter brings snow and rain, you’ll want shoes with plenty of traction to help keep you safe. Leather boots are a great shoe option that’s comfortable but has enough traction to keep you upright all day. Don’t forget to add your favorite winter accessories like gloves, a beanie, or a scarf for extra warmth. If you bring these winter accessories with you on your trip, ensure they are in a similar tone to any belt or shoes, for some uniformity in your look. 

Spring winery outfit guide

Man looking at a wine bottle
Michael Kahn / Unsplash

Once the flowers bloom, it’s the perfect time to shed some layers on your next winery trip. The spring season is also the best time to experiment with slightly more colorful and playful outfit choices, meaning it’s a great time to bring out your printed shirts. A striped button-down or any minimally printed top is a great option to help bring your look to life. If you’re keen on solid colors, opt for slightly more playful colors, such as pastels, to help celebrate the season. If you opt for a white button-down, you can also choose to add a linen blazer on top for a more sophisticated option that won’t be too heavy.

As with the other seasons, it’s best to keep your choices for your slacks or pants a solid color. However, unlike most seasons, spring is the perfect time to bring out your lighter-colored pants such as a light blue or tan, which can bring a more airy effect. 

Stick with dressier shoes or sneakers for your look, and don’t forget helpful spring accessories like sunglasses or the occasional umbrella. While cold weather isn’t typically a problem, spring showers can affect your winery trip, meaning it’s best to be prepared with an umbrella on hand.

Leslie Leon
Leslie is a Los Angeles-based writer and content creator. She is always researching and finding the latest fashion trends…
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