Fall is the best time to experience wine country and the best time to dress up for it too. If you’re planning wine tasting in cool weather, here is a glimpse of some ideas for you. 

First I want to apologize to all these beautiful models. In an effort to keep their privacy, I removed as many of their faces as possible as I do not have permission to use their photos.

There are photos of women with sunglasses because the glasses,… well, the glasses just made that much more of a statement.

These women and men were just fabulous.

It’s important to see friends and spend time together as I get older. However, when I was invited to a Food and Wine Festival, I wasn’t asked twice. These events are typically very short. There is only a couple of hours to have time to sip as much wine as you can so in just a matter of minutes, I had to figure out what the take-home was to report back. 

And the one take-home to report, other than having a total blast with one of my best friends was the fashion. I dedicate this to my friend Cynthia who has always been talented when it comes to fashion. Ever since being preppy was cool in grade school.

First, there are the Boots

I love boots. From cowboy, high-heel, ankle, print, and flat boots; I can wear any outfit with them and when it comes to wine country, you can’t go wrong with any pair.

When I took the photo above, I was just looking at the Doc Martens styled with a long flannel but when I did a double-take on the men’s boots, I noticed how stylish they were - for a guy!

It takes a lot of panache for a man to wear these ankle boots and this guy certainly had the confidence in them. 

Hats

Hats are all about keeping your face from too much sun exposure and keeping you warm in the Fall and Winter seasons. In the spring and summer, it’s a matter of keeping the sun from the face but in the winter, this is when a country-cowboy-felt hat can go a long way. 

I picked a hat that was warm with a narrow rim just enough for a little shadow. I also felt I couldn’t go wrong choosing it in black. However, don’t skimp on the color. The right color can fits the right kind of outfit. 

The trick is not whether you have the face for wearing a hat or not. It’s how you wear a hat that makes all the difference. A hat should always meet the rim of your forehead and your hair whether pulled back or not, should go underneath, (not inside your hat).

Casual

If you just want to be as comfortable as possible, you can still look chic. A nice flannel around your waist, a beanie (instead of a country hat), and a crossbody purse - why not?

The men can get away with a khaki baseball cap and flip it backward IF it fits the attire. (Any sports baseball hat, on the other hand, let me just put it this way; I wouldn’t highlight that at all.) 

This guy seemed like he was paired with the fashionably casual gal and they certainly looked great together even if they weren’t together.  

Fringe

And for those of you who like to be on the fringe of fashion, these were killer boots!

I love to see fringe, whether on your purse or boots. Maybe not so much on your jacket unless it’s REALLY fashionable, (otherwise skip the fringe on your jacket) but these boots looked comfortable, stylish, and oh-so-chic!

Long Coats/Sweaters/Flannel Kimonos

This was very nice to see. I see a lot of flowery kimonos in Spring but a flannel kimono was kickin’! What a way to feel like your outfit is flowing as much as the wine and turning that flannel into something feminine got 5 stars.

Pull out those long Southwestern sweaters that you thought you’d never wear when you got one for Christmas. They actually are perfect for none other than wine tasting. They’re very chic and can go with anything from Doc Martens to ankle boots to high heels. Pair it with a crossbody purse and you’ll be fashionable as well as warm. 

Pulling it all together

Regardless if you just have the boots, the hat or the scarf, pulling it all together not only takes gumption but confidence that you really know your fashion as well as your wine. 

The black Vans with a long jacket and a beanie is just fun.

So regardless if you don’t know a lick about wine, if you have an outfit pinned down to the nines, you’ll fit right in!

The black belt with the black hat and black ankle boots highlights a beautiful figure.

Strike a pose

No matter what, just don’t forget to strike a pose. If you’re not wearing a hat, let your hair down. Let it flow over your shoulders. Wine is made to make you feel relaxed and having your hair down is what it’s all about - the mood!

Don’t hesitate to look relaxed. Whether you’re standing, laid back on an Adirondack chair, legs crossed or not, just remember that the art of wine country chic is being relaxed: chill.

Wine can be intimidating but if you can wear your fashion confidently, you’ll fit right in whether you know the difference between Cabernet Sauvignon and Pinot Noir - or not.

How you pose is not just for your photos, but for taking a breath between tastings. You’ll look chic and confident.

And don’t forget your sunglasses!

Feel free to let me know what your favorite outfit is when you go wine tasting below. 

Cheers!