Winter Wine Tasting Outfits That are Chic and Cozy

There are many ways I love to spend my free time. One of them? Wine tasting.

There are few things more relaxing and indulgent in my mind, and heading out on a wine country getaway will never fail to make me happy. The slower pace of this activity coupled with great sips, good company, and beautiful scenery is simply hard to beat.

If you’re heading out on your own little trip, I hope you find this post as a source of inspiration on what to wear wine tasting (specifically during the fall and winter months.) After my trip to Napa Valley, I learned what was truly worth packing and what could have been left behind.

In California wine country, the climate can be somewhat moody, with comfortable temps during the day and a much cooler vibe at night. This makes layering key and it also means packing the right type of shoes is a must.

Below, I’m sharing a handful of outfits I wore during our recent trip. While these looks are specific to the cool season, I also think they would be good options for the spring. Plus, even if you’re heading to a different wine region, these outfit ideas are chic, practical, and fitting for a day spent sipping vino!

Winter Wine Tasting Outfits

Shop Here: My Recent Wine Country Outfits

Long Sleeve Maxi Dress and Ankle Boots

Summer wine country trips might call for short dresses, but a colder climate shouldn’t stop you from flaunting a similar look. Make things seasonally appropriate by opting for a maxi dress. This long sleeved printed pick was the perfect choice for my trip — it looks slightly festive (we went right before the holidays) while maintaining a classic feel.

I styled the dress with my favorite pair of ankle booties. These have a heel that gives them a more “dressed up” look yet they’re still easy to walk in. For an added layer, you could go with a simple wool coat or something with some texture, like this faux fur jacket. This outfit is ideal for wine tastings that fall later in the afternoon and into the evening.

Collared Tweed Jacket and Pants

Need a wine tasting outfit that you could wear from day to night? This would be my go-to recommendation. It’s timeless and comfortable, which is the ideal combo if you ask me. To replicate the look, style some satin pants with a knit vest or a sweater — I adore the olive green color on both of the pieces I’m wearing. Oh, and when traveling in the fall or winter, keep warm with a layer like a simple cardigan or a tweed jacket.

I’m wearing the same ankle booties here as I was in the photo above. They really are a versatile pair of shoes and I love that I could pack them and style them with multiple looks!

Sweater and a Satin Slip Dress

Because we were visiting wine country close to the holiday season, I wanted to wear at least one outfit that had a festive feel. To achieve that vibe, I paired a sparkly sweater with a satin slip dress. This sweater almost has a tinsel look to it, and it comes in several color options as well. It would look adorable with other bottoms, like jeans or a mini skirt, for any holiday parties. For a more everyday feel, you could swap the sparkly sweater for something plain, like a cream colored knit or a button up cardigan.

I will say that a slip dress is definitely a “must pack” item when traveling to wine country in the fall or winter. You can pair this piece with so many different tops and you could rewear it throughout your trip if you’re tight on luggage space.

This is the exact one I’m wearing and I have to say it’s worth investing in quality here — it’s a staple you’ll have in your wardrobe for years to come (and it can be styled for all the seasons!)

Cashmere Sweater and a Blazer With Leggings

Who said black leggings can’t be dressed up? The key is finding a pair that’s on the thicker side (which will give things a higher end look.) These are my go-to as of late, and I love that they can be worn with just about any outfit.

I styled them here with a graphic sweater and one of my all-time favorite blazers. For shoes, I opted for tall boots just to mix things up. This shoe choice is ideal for cooler temps as you get more leg coverage than you would with ankle booties, sneakers, or heels. If you’re looking for a new pair, I’d highly suggest these. While they are an investment, they’re made with quality that can’t be beat.

Cardigan With Straight Leg Jeans and Boots

Regardless of the season, you can’t travel anywhere without a good pair of jeans. I’m of the mindset that it’s best to pack just one pair that you can wear with various tops, shoes, and layers. I’ve been wearing these straight leg jeans on repeat and I’m a big fan of the darker wash and high rise fit!

This look might be simple, but you really can’t go wrong by styling a cardigan with denim and some booties. Adding a belt can create more visual interest as it helps to break up the pieces you’re wearing. These Amazon belts are sooo cute and they look much more expensive than they really are.

Whether you’re wine tasting or you’re exploring the nearby shops, this look is an easy go-to.

Faux Fur Jacket With Leggings and Loafers

On our way out of Napa, we decided to spend some pre-flight time in San Francisco. This is the outfit I chose to wear while exploring the city. I needed something that maxed out my comfort (since I’d be wearing it on a plane) while also looking pulled together.

I realize this look isn’t “wine country” specific, but I wanted to include it in case you’re also looking for a chic winter travel outfit or something more laid-back.

Which winter wine tasting outfit idea is your favorite? Let me know in the comment section below!