Packing for Vermont
Six days of fall outfits to wear in Woodstock - or wherever autumn takes you.
Six days in Vermont means plenty of layers, comfortable shoes, and a little planning. I wanted everything I packed to feel polished but practical - from bike rides and days in Woodstock to dinners out. These are the looks coming with me, but none of them require a trip to Vermont.
Start with a color palette.
When I’m packing for a trip, I like to start with a color palette. It makes getting dressed easier, keeps me from overpacking, and means almost everything in my suitcase can work together. For Vermont, I’m sticking with five fall favorties: burgundy olive, navy, chocolate and camel. They mix easily, feel right for the season, and - most importantly - work well beyond a week in Woodstock.
A Travel Outfit That’s Comfortable Yet Polished.
These Aritzia lodge pants are one of my favorite wardrobe essentials! They are basically like wearing pajamas and they wash well and don’t wrinkle! I love wearing them as a monochromatic set, which I think always looks chic!
Unfortunately, my actual luggage is no longer available, but I have linked a similar option to a luggage set Ava owns in a different color. She loves hers!
The duffel bag is the Béis Mini Weekender, which was made to fit under airplane seats and counts as a “personal item.”
Back home, this outfit is one I’d wear on a normal Mom-day of running errands, doing things around the house, or an impromptu lunch with friends.
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Pants · Sweater · Purifying Mist · Duffel · Sneakers · Book · Similar Luggage
Evening in Woodstock
For our first night in Vermont, I wanted something that felt a little special for dinner at the Red Rooster without feeling overly dressed. I’m starting with warm chestnut, chocolate and ivory, then adding burgundy — the color I’ll keep coming back to all week.
The bag is the star of the show for this outfit! I have this Strathberry Mini Tote in Oat and I absolutely love it, so I died when it came out in burgundy croc! It’s the perfect size for essentials, and works just as well during the day as it does for dinner!
Back home, this is an outfit I would wear to church or to dinner out with my hubby.
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Country Roads and Covered Bridges
Day two is all about getting outside. We’re renting e-bikes to ride the back roads around Woodstock, see a few covered bridges, and soak up the fall leaves before ending with a stroll through the village.
Layers are everything for a day like this. Mornings in Vermont can be chilly, so I’m starting with a blue stripe Oxford button-down under a cream cable-knit sweater, then topping it all off with my Barbour jacket. My favorite slightly baggy straight-leg jeans and suede boat shoes keep it comfortable (and I won’t be slipping off the pedals!), and my classic saddle bag can be worn crossbody for a hands-free ride.
Back home, this is my go-to for an easy Saturday or any fall weekend when I want to look put-together without trying too hard.
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Jacket · Hood For Jacket · Jeans · Shirt · Sweater · Shoes · Bag · Sunglasses · Water Bottle
Tavern Night at Richardson’s
For our second night, we’re heading to Richardson’s for drinks and dinner, so I wanted something cozy but still a little dressed up. An ivory cashmere turtleneck and my favorite classic straight-leg jeans are an easy base, and brown leather ballet flats (one of my most favorite shoe brands) keep it polished without trying too hard.
The real star is this olive cape coat. I’ve had my eye on it forever, and this trip finally gave me the excuse I needed! It’s warm, it’s chic, and it instantly makes jeans feel like an outfit.
You might notice the saddle bag from Day 2 making another appearance. Repeating accessories is one of my favorite packing tricks, since a few pieces that work with everything means less in the suitcase and more outfit options.
Back home, this is exactly what I’d wear to a casual fall date night or dinner with girlfriends.
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A Walk in the Woods
Day three, we’re heading into the Green Mountains for an easy hike and as much fall foliage as we can take in. I wanted something cozy and practical, but still cute enough for a lunch stop on the way back into town.
I know, I know, the pumpkin sweater is a little cheesy. But I mean… when in Vermont! To keep it from going full costume, I’m layering it over a green striped button-down with a little ruffle collar that peeks out at the neck and cuffs, which makes the whole thing feel a bit more polished. The same baggier straight-leg jeans make another appearance (repeat offenders are the secret to packing light!) and suede Chelsea boots with a lug sole give me grip on the trail without looking like hiking boots.
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Cashmere and Charcuterie
Wes is definitely going to ask if I packed anything besides turtlenecks. The answer will be “no,” and I regret nothing. The J. McLaughlin Arlette cashmere is the base layer of my entire personality from October to March. I own it in every color. To me, there’s just something sophisticated about a turtleneck. This one is the perfect weight, and the little button details at the sleeve make it feel so polished. Add my hubby, a cheese board, and a craft cocktail — that’s my idea of the perfect night.
And yes, those are my all-time favorite ballet flats — they’re getting their own post soon, so stay tuned.
I own a different coat than the one I’m linking. The one I’ve linked is a classic that will forever be in style. Plus, it’s 100% wool and a complete steal!
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Pants · Turtleneck · Flats · Bag · Coat Similar To The One I Own
Plaid, Please
Yes, that’s the Arlette turtleneck again, this time in olive. I warned you I own it in every color, and I wasn’t kidding. But let’s be honest, the real star here is this plaid jacket. It might be the most Vermonty thing I’ve ever owned, and I can’t wait to wear it strolling through Quechee, watching the glassblowers at Simon Pearce, and having lunch by the falls.
Now, a quick jeans note (they’re getting their own post soon). I’m packing two straight-leg styles and alternating them all trip. The Levi’s 501s are my classic, slender straight-leg for when I want to look a little more polished, especially with ballet flats. The Levi’s 501 ‘90s are slightly baggier and more relaxed for laid-back days. For Quechee, I haven’t decided witch pair wins yet. Either way, with boots and this jacket, I think it works.
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Jacket · Jeans · Boots · Bag · Turtleneck · Sunglasses
Worth Every Wear
Let’s talk about this shirt, because I know it’s a splurge. I went back and forth for a long time before buying it, and in the end I chose two classic colors, white and blue, and treated them as an investment. They’re the kind of pieces I’ll reach for for years, and with brown velvet pants and slingbacks, it feels just right for dinner at Oakes & Evelyn. I’m also putting together a post with beautiful alternatives at friendlier price points, because a great white shirt shouldn’t have to break the bank.
The same goes for this cashmere wrap. When I bought my first one, I honestly wasn’t sure I’d use it enough to justify it. I was so wrong. I now own it in several colors and use it constantly, year-round: on planes, at chilly dinners, and layered over dresses and simple T-shirts. This chocolatey taupe is my cozy fall and winter pick. If the price gives you pause, I’ve also found some lovely alternatives that give you the same cozy, polished look for less, and I’ll link those soon. Either way, consider this your nudge. You’ll use it more than you think.
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Scarf Coat Secrets
Remember that plaid jacket from Quechee? Here’s a secret: it’s actually a scarf coat, and the scarf comes off. So today I’m borrowing it for a pop of color, and suddenly one piece is doing double duty.
Underneath is one of my all-time favorite styles, the classic J. Crew cotton rollneck. I’ve tried plenty of versions, and none of them quite match the fit and feel of the original. It’s relaxed without being sloppy, and substantial without being bulky. Add comfy sneakers for a long bike ride, a crossbody to keep my hands free, and a day of back roads and foliage, and I’m a happy girl.
Love the plaid but not ready for the whole coat? I’ve linked a similar scarf below that gives you the same pop of color and pattern.
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Sweater · Jeans · Bag · Shoes · Sunglasses · Alternative Plaid Scarf · Coat With Scarf
Olive You, Coat
For our last night, this cape coat is the star of the show. The olive is so rich, and I love it over a sleek black cashmere turtleneck and slim black pants. It’s simple underneath, so the coat gets to do all the talking.
Now, the leopard clutch. I’d been eyeing some pricier versions, and while I truly consider leopard a neutral, prints can come and go. I just couldn’t justify spending big on one. Then I found this beauty for a fraction of the price, and it’s my surprise steal of the trip. Proof that you don’t have to splurge on everything to look polished.
And finally, I’m bringing back my old signature scent, Chanel Coco Mademoiselle. It’s a true classic, and I wore it constantly when my kids were little. To this day, if they catch a whiff of it, they say it smells like Mom. I can’t think of a sweeter compliment.
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Coat · Turtleneck · Pants · Shoes · Perfume
Same Outfit, No Shame
If it worked on the way here, why change it? I’m copying and pasting my travel day look for the trip home, and I’m not even a little sorry. These pants are seriously a wardrobe staple for me, and I love to pair them with monochromatic layers.
This time I’m linking a more budget-friendly hypochlorous acid spray that I use constantly. I’m convinced it cures everything!
The original Experiencing God study is a longtime favorite, and travel days are some of my best uninterrupted time to dig in.
Then home sweet home, with a camera roll full of fall foliage.
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Pants · Sweater · Shoes · Alternative Spray · Duffel · Similar Luggage Ava Owns · Book
