Winter in Woodstock
📍 Woodstock, Vermont

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Dress || Jacket (Similar) || Heels || Similar Handbag || Tights || Earrings

If there’s one place that embodies the magic of winter in New England, it’s Woodstock, Vermont. With snow-dusted trees, charming colonial buildings, and the cozy warmth of the Woodstock Inn, this town feels like stepping into a storybook. Recently, I had the chance to spend a day here, and it was nothing short of enchanting. Dressed in a chic yet practical outfit for dinner — my faux fur jacket layered over a classic Black Watch tartan dress from Tuckernuck, paired with Sarah Flint heels — I felt perfectly suited for the picturesque backdrop.

A Stay at the Woodstock Inn

The Woodstock Inn is the centerpiece of this idyllic town, and for good reason. From the moment you step inside, you’re greeted with roaring fireplaces, inviting seating areas, and the warmest hospitality. The rooms are a perfect blend of modern luxury and traditional New England charm, with cozy bedding and thoughtful touches that make you feel right at home. During your stay, you can take full advantage of the on-site amenities, from the indulgent spa treatments to the outdoor fire pits. It’s not just a place to stay — it’s an experience that immerses you in the magic of Vermont winters.

Dining at the Red Rooster

No visit to the Woodstock Inn is complete without a meal at the Red Rooster, the inn’s signature restaurant. The menu is a love letter to Vermont, featuring locally-sourced ingredients crafted into refined, seasonal dishes. I opted for the New England clam chowder squash soup followed by the chicken salad sandwich, both of which were absolutely delicious. The atmosphere strikes the perfect balance between upscale dining and laid-back comfort, making it an ideal spot to linger over a meal. And don’t skip dessert — the maple bread pudding was the perfect sweet ending to a cozy evening.

Exploring Woodstock in Winter

Beyond the inn, Woodstock offers plenty to explore, even in the chill of winter. A stroll down Main Street reveals an array of boutique shops and cafes, all adorned with twinkling lights and festive wreaths. We spent quite a bit of time at F.H. Gillingham & Sons, a general store that’s been a Woodstock staple since 1886, picking up locally-made maple syrup and woolen mittens. For a bit of outdoor adventure, nearby Billings Farm & Museum is a must-visit, offering everything from sleigh rides to interactive exhibits about Vermont’s agricultural history. Whether you’re exploring the town or taking in the serene snowy landscapes, there’s a sense of timeless charm that makes Woodstock unforgettable.

Woodstock in winter is a destination that feels both elegant and down-to-earth, a perfect blend of refined experiences and cozy comforts. Whether you’re savoring a gourmet meal at the Red Rooster, curling up by the fire at the Woodstock Inn, or strolling through the town’s snow-dusted streets, every moment feels special. And while the backdrop of this charming town was undoubtedly stunning, I’d like to think my outfit — a classic mix of faux fur and tartan — added its own little touch of sophistication to the scene. If you’re looking for a winter getaway that feels straight out of a postcard, Woodstock, Vermont, should be at the top of your list.

Love from Vermont,
Katie

Thanks for stopping by! To keep up with all things about my travels and style, be sure to visit throughout the week! Be sure to check out my exclusive adventures in NYC and New England.

Après-Ski Inspired Style
📍 Stowe, Vermont

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Jacket (Similar) || Turtleneck || Jeans || Boots || Similar Handbag || Beanie

Confession time: I don’t ski. Not even a little. While others are gracefully carving down the slopes, I’m the one sipping hot cocoa by the fire, perfectly content in my cozy layers. Honestly, I think I’d spend more time on the ground than upright if I tried. But here’s the thing: you don’t have to ski to embrace the effortless, chic style that comes with an alpine getaway. The refined elegance of après-ski style is all about staying warm, comfortable, and looking put-together—whether you’re in the Alps or a snowy Vermont village like I recently visited.

The beauty of après-ski style lies in its versatility. With a few thoughtful wardrobe staples, you can easily channel the polished, cozy vibe that feels just as at home in a ski lodge as it does strolling through a snowy town. Here are my essentials for nailing the look:

Plush Faux Fur Outerwear

Nothing says alpine chic quite like a statement faux fur jacket. Not only does it provide warmth on those crisp winter days, but it also instantly elevates your outfit. I’m partial to a sleek black or deep brown faux fur coat, like the one I wore during my Vermont trip. It’s versatile enough to pair with anything—from jeans to tailored pants—and the soft texture gives off a luxurious, cozy vibe. Plus, a well-chosen coat can turn even the simplest outfit into a winter fashion moment. Whether you’re heading out for a coffee run or posing for photos in front of a snow-dusted chalet, a plush coat is a must.

Cashmere Sweaters

A quality cashmere sweater is one of the most versatile pieces you can pack for a winter getaway. Lightweight yet incredibly warm, cashmere is perfect for layering under coats or wearing on its own indoors. Neutral tones like camel, ivory, and gray are timeless and easy to style, but don’t shy away from a pop of color if it suits your mood. What I love most about cashmere is how it feels against the skin—soft, breathable, and never bulky. It’s ideal for those cozy moments by the fireplace or paired with tailored trousers for an effortlessly sophisticated look.

Tailored Pants or Denim

When it comes to bottoms, tailored pants or high-waisted black denim are my go-to options. They’re comfortable enough for all-day wear yet polished enough to transition seamlessly into the evening. For my Vermont trip, I opted for sleek black denim, which worked beautifully with my faux fur jacket and cashmere layers. The key is to choose pieces that fit well and have a bit of structure—nothing too slouchy or oversized. Bonus points if they’re slightly cropped to show off your winter boots!

Stylish Winter Boots

Speaking of boots, finding the perfect pair is essential for après-ski style. Look for a pair that combines practicality with elegance, like sleek leather or suede Chelsea boots with a sturdy sole. During my trip, I relied on my Margaux Chelsea boots, which offered both comfort and sophistication. They’re waterproof (a must for snowy conditions) and versatile enough to wear with everything from jeans to dresses. A chic pair of boots can tie your entire outfit together while keeping your feet warm and dry.

Wool or Cashmere Accessories

No winter outfit is complete without the right accessories. Wool or cashmere beanies, scarves, and gloves not only keep you cozy but also add an extra layer of texture and sophistication to your look. I’m a fan of neutral accessories that complement the rest of my outfit, but you could also use this as an opportunity to play with patterns or subtle embellishments. A well-chosen scarf, for example, can double as a shawl indoors, while a classic beanie keeps you looking effortlessly cool on a snowy day.

Elevated Base Layers

Base layers don’t have to be boring! Opt for pieces made from merino wool or other breathable fabrics that keep you warm without adding bulk. I love a slim-fitting turtleneck in a neutral color, which works beautifully as a standalone piece or as a layer under heavier sweaters and jackets. These elevated basics are the unsung heroes of après-ski style—you may not see them, but they’re doing all the heavy lifting when it comes to staying warm and stylish.

Statement Sunglasses

Don’t underestimate the power of a good pair of sunglasses—even in the snow. The glare from the sun reflecting off the white landscape can be intense, making sunglasses a practical necessity. But they’re also a fantastic way to add a touch of glamour to your outfit. Oversized frames or aviators are my top picks for a classic, polished look. Plus, they’re perfect for those sunny, snow-covered strolls through the village.

Sleek Base Outfit for Dining

After a day out in the cold, there’s nothing better than warming up with a cozy meal in a beautiful setting. For evenings out, I love to pack a sleek base outfit that can easily be dressed up or down. A sweater dress or a chic trousers-and-top combo works perfectly. These pieces are comfortable enough for lingering over dinner yet polished enough to feel put-together. Add a pair of statement earrings or a bold lip color, and you’re ready to enjoy a refined après-ski dinner.

Whether you’re sipping mulled wine by the fire or wandering through a picturesque ski town, après-ski style is all about combining comfort and elegance. You don’t have to hit the slopes to embrace this cozy, chic aesthetic—just a few thoughtfully chosen pieces will have you looking the part. So grab your faux fur coat, your cashmere layers, and your favorite pair of boots, and let the snowy adventures begin!

Love from Vermont,
Katie

Thanks for stopping by! To keep up with all things about my travels and style, be sure to visit throughout the week! Be sure to check out my exclusive adventures in NYC and New England.

Baby’s First Snow Day
📍 Vermont

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Sweater || Jeans || Boots || Coats || Earrings
B: Bunting || Fleece Hat

There’s something magical about experiencing the first snowfall of the season, but watching your baby experience their first snow day takes it to another level. While visiting Vermont over the holidays, Brennan and I stepped outside to enjoy the pristine, snow-covered landscape. Bundled up and ready for the chilly weather, we made memories I’ll treasure forever.

For our outing, I layered up with some of my favorite winter wardrobe staples: a cozy camel cardigan from Sézane, paired with their classic Le Crop Jeans, and my trusty Margaux Chelsea Boots, perfect for staying stylish and sturdy on snow-covered ground. Brennan, of course, stole the show in an adorable bear bunting suit from L.L. Bean, complete with little ears on the hood that made her look like the sweetest snow bear in Vermont.

Getting outside in the cold with a baby might seem daunting, but with a few tips and proper preparation, it can be a truly enjoyable experience:

Dress Your Baby in Layers

Keeping little ones warm is key, and layering is the best way to ensure they stay cozy and comfortable. Start with a breathable base layer like a cotton or merino wool onesie and leggings to trap warmth close to their body. Add a second layer, such as a soft fleece or thermal romper, for extra insulation. Finally, finish with a fleece bunting suit like Brennan’s—bonus points if it’s as adorable as ours from L.L. Bean! Don’t forget thick socks, mittens, and a hat that covers their ears. These small details go a long way in keeping your baby warm and happy in chilly conditions.

Choose the Right Timing

Timing is everything when it comes to enjoying the cold weather with a baby. Mid-morning or early afternoon is often ideal because the temperatures are slightly warmer, and babies tend to be well-rested after their first nap. Avoid venturing out during windy or overly frigid conditions, as it can make the experience uncomfortable for everyone involved. We headed out mid-morning, and the sunlight reflecting off the snow not only made for stunning photos but also helped keep the chill at bay. Make sure to check the weather forecast and aim for a day with little to no wind for the most enjoyable outing.

Limit Time Outside

Even with all the right gear, babies are more sensitive to the cold than adults, so it’s important to keep outdoor adventures short and sweet. Aim for 20–30 minutes at most, especially if your baby is under a year old. Be sure to observe them closely for signs that they might be getting too cold, like fussiness, a red nose, or cold hands despite their mittens. For Brennan’s first snow day, we spent about 15 minutes outside, which gave us plenty of time to soak in the scenery, snap some photos, and enjoy a few giggles before heading back inside. It’s all about quality, not quantity, when it comes to winter outings with little ones.

Plan for Warm-Up Breaks

After your snowy adventure, it’s important to have a warm and cozy space to return to. Before heading outside, I made sure our indoor space was prepped with blankets, hot drinks, and a warm change of clothes for Brennan. Once we came back inside, I swapped her out of her bunting suit into a soft fleece romper and wrapped her in a blanket for extra warmth. I enjoyed a steaming cup of hot cocoa while Brennan had a few cuddles to warm up her little hands. These warm-up breaks not only ensure your baby stays comfortable but also give you both a chance to relax.

These moments are fleeting, so take the time to snap a few photos to preserve the memories. Brennan’s bear suit made for the sweetest pictures against the backdrop of Vermont’s winter wonderland. This snowy adventure reminded me that some of the most meaningful experiences happen when we step outside, even on the coldest of days. Here’s to many more snow days filled with giggles, rosy cheeks, and cozy outfits!

Love from Vermont,
Katie

Thanks for stopping by! To keep up with all things about my travels and style, be sure to visit throughout the week! Be sure to check out my exclusive adventures in NYC and New England.