Step into the Weekend
Happy Friday, Grit & Glammers! I’m home from Seaside, Florida — and y’all, I had the best time. Four days at the Seeing Red Wine Festival. Great wine. Excellent food. And those white picket fences that make Seaside look like a movie set. (Because it was one.)
This week I’m sharing what to wear to a wine festival — every look, from the Vintners Dinner to the drive home — plus the event I can’t stop talking about and one tasting trick I’ll use for the rest of my life. Let’s dive in.
Short on time? Shop all five looks in one place → Shop All Five Looks
Key Takeaways
- Wear layers. A wine festival runs from cool mornings to sunny tents to chilly evenings outdoors.
- Wear shoes you can stand in all day. Loafers and flats beat heels on grass, brick, and sand.
- Taste like a sommelier: hold the wine in your mouth for at least eight seconds, swish, then swallow.
What Should You Wear to a Wine Festival?
Polished layers and shoes you can actually stand in. Most wine festivals are outdoors, and you’re on your feet for hours — cool mornings, sunny tents, chilly nights. Start with a jacket you can take off, add pants you can move in, and finish with loafers or flats. Save the pale colors for the dinners where you’re seated. (I know, I know. I wore ivory to a red wine dinner anyway. More on that below.)
My Favorite Event: The Battle of the Somms
Hands down, the Battle of the Somms was my favorite. Brilliant. Two Master Sommeliers — Larry O’Brien and Thomas Price — went head-to-head, course after course. Chef Roy Khoo of Ithaka Hospitality and Chef Nikhil Abuvala of Seaside’s Daytrader did the cooking. Each sommelier paired what he believed was the perfect wine with each course. Then we voted.
The food was excellent. And it was so educational. Taste the same dish with two different wines, and suddenly pairing makes perfect sense.
Here’s the tip I’m bringing home. Keep the wine in your mouth for at least eight seconds. Then swish it around before you swallow. Eight seconds sounds like nothing — until you try it. You’ll taste things in your glass you never noticed before.
Where I stayed: The Court, Seaside’s boutique hotel. A former motor court turned boutique escape, right in the heart of town. Charming doesn’t begin to cover it.
What I Wore to the Wine Festival
Thursday: The Vintners Dinner. Far Niente at Bud & Alley’s — and I went all ivory. A ribbed V-neck cardigan with gold buttons, silk cargo pants, and snakeskin pointy-toe pumps. A brown suede clutch, a gold collar and big gold hoops finished it. Ivory at a red wine dinner? Living dangerously, Gang.
Friday: The Al Fresco Reserve Tasting. Floral jacquard pants. A chunky sleeveless turtleneck. And a brown leather jacket over my shoulders for when the sun went down. Gold block heels and a gold metallic bag pick up the gold in the pants — that’s the trick with a print. Pull one color out and repeat it.
And the evening itself? Spectacular. VIP wines under the tent and out on the lawn, with bluegrass music playing. Elevated and laid-back at the same time. Plus a Lisini Brunello di Montalcino I’m still thinking about.
Saturday morning: The Battle of the Somms. It was a cool morning, so I grabbed my denim jacket with the corduroy trim. Underneath — a plaid flannel shirt and green drawstring cargo pants. Cargo pants at a sommelier’s table? Hear me out. Cinch the hem for a jogger shape, or let it fall straight over a loafer. Add suede loafers, and you’re polished enough for a Master Sommelier and comfortable enough for a morning on your feet.
- Outfit formula: denim jacket + plaid flannel shirt + utility pants + suede loafers
Saturday afternoon: The Grand Tasting under the VIP tent. A striped tuxedo shirt, navy taffeta drawstring pants, and cream, red, and navy flats. Plus a little red bag. It is called Seeing Red, after all.
Sunday: The Celebration of Bubbles — then home. Travel day calls for soft. Not sloppy. Soft. A quilted camel jacket over a gray quarter-zip and joggers, with suede loafers. Comfortable for the drive and still put together. (More travel packing ideas in what I packed for a fall wedding weekend.)
Shop all five looks from the weekend in my ShopMy collection → Shop All Five Looks
Beauty Notes
A weekend of sun, salt air, and red wine? Your skin wants a drink too. Here’s what’s on my list.
- Dewsy Hydrate & Firm Body Care Bundle — Starring the HA Body Serum. We spend so much time on our faces and forget everything below the neck. Not anymore.
- Hanacure The All-In-One Facial Set — The Peptide Lifting Treatment. A facial at home, no appointment required.
- Josie Maran Vanilla Vibezzz Whipped Argan Oil — Whipped argan oil that smells like vanilla. Need I say more?
- Salt & Stone Stocking Stuffer Set — Yes, I’m already thinking about stockings. A gift for her and a little something for you.
Accessories That Go From Tasting to Dinner
- A Little Red Bag — A wine-red top-handle bag. It goes with everything — navy, olive, ivory, you name it.
- Pearls — Pearls with a plaid shirt? Absolutely. Pearls make casual look finished.
- A Bee Brooch — Y’all know I collect them. Pin one on a denim jacket lapel — instant conversation starter at the tasting table.
- A Silk Scarf — Tie it on your bag at noon. Wrap it around your shoulders when the sun goes down.
- Gold Hoops — Denim at 10 AM. Ivory at 7 PM. Same hoops.
- A Tweed Handbag — Fall and winter perfection. Period.
Cozy Pick of the Week
Minky Couture HUGS Blanket — Seaside nights got chilly once the sun went down. This is exactly the blanket you want for that. Plush, soft, and machine washable — in sizes from Travel to Monster. (Yes, Monster.) The Travel size goes along for outdoor evenings; the Monster stays on the sofa for movie night. And how pretty would one be under the tree?
A Few More Favorites
- Crate & Barrel Hip Wine Decanter — After the Battle of the Somms, I want my wine to breathe at home too. This curvy carafe is a Crate & Barrel exclusive and a bestseller — and at $39.95, it’s a lovely hostess gift with a bottle tucked alongside.
- Warby Parker Tortoise Color Block Sunglasses — Midday under a white tent is bright. These are from the fall collection — classic shapes with one shade on the front and another on the arms. They start at $95 and block 100% of UV rays.
- Lauren Ralph Lauren at Macy’s — Y’all know Ralph Lauren is my forever brand, and Macy’s carries a plethora of it. Love these Over the Knee Boots
- Antique Candle Co. Maple Pumpkin Waffles — Their brand-new fall candle, picked by their own candle testers. 100% soy wax, a cotton wick, and that old-timey zinc lid. How cute is that?
Sales Worth Your Weekend
J.Crew’s More Is More Sale is on — and here’s what I’m eyeing:
This Week’s Favorites
Here’s what you couldn’t stop adding to your cart. No hints. You’ll have to click.
Five · Four · Three · Two · One
What’s Good?
Now it’s your turn, Gang. A favorite wine? A festival you love? A tasting trick of your own? Tell me in the comments.
Closing Thoughts
I came home from Seaside with a full heart and a brand-new way to taste wine. Eight seconds. Swish. Swallow. Whatever you’re pouring this weekend — take your time with it. Cheers, Grit & Glammers.
Style has no expiration date — and neither do you.
Frequently Asked Questions
What should I wear to an outdoor wine festival?
Wear layers and comfortable shoes. A jacket you can take off, pants you can move in, and loafers or flats will carry you from a cool morning to a sunny afternoon tent.
Can you wear white or ivory to a wine tasting?
You can, but save it for a seated dinner. At a walk-around tasting, red wine and crowds make pale colors a risk.
How do sommeliers taste wine?
They take their time. Hold the wine in your mouth for at least eight seconds, swish it around, then swallow. You’ll pick up far more flavor.
What shoes are best for a wine festival?
Loafers, flats or low boots. You’ll stand for hours on grass, brick or sand, so skip the heels.
What is the Seeing Red Wine Festival?
It’s an annual November wine festival in Seaside, Florida, with vintner dinners, reserve tastings, the Battle of the Somms and a Grand Tasting in Central Square.
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Browse my full ShopMy storefront for outfits, home, and more.
Shop All Five Looks: What I Wore to a Wine Festival → Shop All Five Looks
Vintners Dinner
Al Fresco Reserve Tasting
- Jacquard Pants
- Similar Pants
- Similar Pants
- Similar Chunky Turtleneck
- Brown Leather Jacket
- Gold Block Heels
- Gold Metallic Handbag
Battle of the Somms
Grand Tasting
Travel Day
J.Crew More Is More Sale
Beauty Notes
- Dewsy Hydrate & Firm Body Care Bundle · HA Body Serum
- Hanacure The All-In-One Facial Set: Peptide Lifting Treatment
- Josie Maran Vanilla Vibezzz Whipped Argan Oil
- Salt & Stone Stocking Stuffer Set
Accessories
Cozy Pick
- Minky Couture HUGS Blanket
- Minky Couture HUGS Blanket, Travel Size
- Minky Couture HUGS Blanket, Monster Size
A Few More Favorites
- Crate & Barrel Hip Wine Decanter
- Warby Parker Tortoise Color Block Sunglasses
- Ralph Lauren Over the Knee Boots at Macy’s
- Antique Candle Co. Maple Pumpkin Waffles
Amazon Goodies
In case you missed them: Christmas Gifts for Her and Bedroom Refresh. And a few more Amazon favorites this week:
Five · Four · Three · Two · One
Before You Go
What’s your go-to outfit for a day of wine tasting? Tell me in the comments.
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