Cozy Weekend Getaway Packing List

September 23, 2025

Wit & Whimsy Cozy Weekend Getaway Packing List featuring 12 fall essentials: matching lounge set in taupe, tan field jacket, cream cashmere sweater, navy striped sweater, camel beanie, brown lug sole boots, suede ankle boots, Adidas sneakers, dark wash jeans, camel sweater dress, beige cashmere wrap, and suede bucket bag

There’s something special about a weekend escape in the Fall! The crisp air, the crunch of leaves underfoot and of course the excuse to layer on your softest knits and spend time tucked away somewhere charming. Whether you’re heading to the countryside, a cozy inn upstate or even just taking a short city staycation, having a well-planned weekend getaway packing list can truly set the tone for your trip.

From versatile sweaters to smart footwear choices, these are the 12 must-pack Fall essentials for a stylish and comfortable weekend getaway.

Cozy Weekend Getaway Packing List

As the founder of En Route to Rêverie I have pretty much perfected the art of packing. Don’t miss my other packing lists plus the packing and travel tips I swear by

When packing for a cozy Fall getaway, I rely on a well-planned weekend getaway packing list to strike the perfect balance between comfort and chic. I also try to pack in one color family to ensure I have maximum versatility among the items I bring. Packing for Fall and Winter getaways is notoriously more challenging than warm weather trips because of all the excess bulk sweater and jackets contribute, so I suggest traveling in your biggest and bulkiest items to free up space in your suitcase. 

Now, more than ever, prioritize comfort over style. After all, a cozy weekend getaway is about relaxing and rejuvenating! 

1. Matching Lounge Set

First things first: downtime. A matching lounge set is at the top of my packing list for every cozy weekend. Whether you’re sipping your morning coffee or relaxing in your hotel room, having a coordinated loungewear set makes even the most low-key moments feel pulled together. This Varley half-zip sweater and the matching wide leg pants are an absolute dream.

Opt for a neutral shade like cream, grey, or camel so you can mix and match the pieces with jeans or a coat if you want to step outside for a coffee run. Bonus: a matching lounge set packs easily and double as pajamas or a travel outfit.

I also love Vuori’s loungewear pieces, especially their oh so soft Dreamknit collection

Related: My Vuori Review

2. Field Jacket

A field jacket or chore jacket is one of the most practical layers you can pack for a Fall getaway. Its farm-inspired silhouette adds just the right amount of structure to otherwise casual outfits, plus they’re usually lightweight but warm enough for chilly mornings or brisk afternoon walks.

Pair it with jeans and sneakers for exploring, or throw it over your lounge set if you’re running to a coffee shop to grab breakfast. Field jackets are also great because they often have lots of pockets (we love!), ideal for stashing your phone, lip balm, or keys.

This plaid Barn Jacket is also perfect for a Fall getaway, as is this denim style

3. Cashmere Sweater

Few pieces feel more like Fall than a cashmere sweater, especially a cozy cashmere turtleneck. It’s warm, timeless and instantly elevates your weekend wardrobe. I always pack one in a versatile neutral (think ivory, grey, or navy) that I can wear multiple ways — layered under my field jacket, or paired with jeans for dinner out. You also can’t go wrong with a classic cashmere crewneck sweater

Year after year I reach for my cashmere sweaters from brands like Jenni Kayne and COS. Use code MEGHANDONO10 for 10% off your purchase at Jenni Kayne!

Related: The Best Cashmere Sweaters

4. Striped Sweater

Longtime followers know a striped sweater always earns a dedicated spot on my Fall packing lists because it adds visual interest without requiring extra effort. It’s a nod to French style that I find myself reaching for again and again, particularly on weekends when I don’t want to overthink my outfits.

Style a striped sweater with jeans and sneakers for a casual daytime look, or tuck it into a skirt or pair with satin pants for a more polished look. The stripes do the styling work for you, making it a great “one and done” piece.

La Ligne makes some of my favorite striped sweaters including the Marina and Mini Marin. Use code MEGHAND10 for 10% off your first purchase at La Ligne!

5. Beanie

Nothing says cozy quite like a beanie. A good knit hat not only keeps you warm on chilly mornings and evenings but also adds that effortless “weekend casual” vibe to your look. I usually pack one in a neutral color (cream or black) that can pair with all of my outerwear.

6. Lug Sole Boots

A cozy Fall getaway often involves long walks — whether through charming small towns, apple orchards or countryside paths! Lug sole boots are my answer to practical footwear that doesn’t sacrifice style, and bonus points if they’re waterproof or water resistant.

The chunky sole is great for grip and comfort, especially on uneven terrain, but when paired with jeans or a sweater dress they feel fashion-forward.

These Freda Salvador lug sole boots have been a staple in my Fall and Winter wardrobe for years, especially because they’re insanely lightweight. Use code WITWHIMSY10 for 10% off your purchase at Freda Salvador! For a more budget friendly alternative, I would recommend these Sam Edelman boots (just make sure you treat the suede before you wear them).

7. Ankle Boots

While lug sole boots are practical, ankle boots are the polished pair you’ll want for dinners out or day trips when you want to feel just a bit more dressed up. They’re sleek, timeless and endlessly versatile.

Choose a comfortable heel height so you can walk in them easily, and pick a neutral shade like black or brown so they’ll pair seamlessly with everything else in your suitcase. I’m really loving kitten heel boots this season as well!

Related: A Roundup of My Favorite Boots and Booties

8. Sneakers

Every good weekend getaway packing list needs a reliable, stylish pair of sneakers. Comfortable for travel days and versatile enough for sightseeing, they’re the pair you’ll end up wearing most often.

I almost always pack neutral colored sneakers (they go with everything from jeans to sweater dresses) and I’ve shared before that sneakers are a non-negotiable for me when packing for trips of any length! This is another pair I own and love for their versatility. 

Related: What Shoes to Pack for Europe

9. Jeans

A pair of well fitting jeans is the anchor of nearly every Fall outfit in my book. They’re practical for daytime adventures, pair well with boots or sneakers and can be dressed up with a cashmere sweater or striped knit for the evening.

I usually reach for a dark wash wide leg pair that feels polished but still casual. Jeans are also easy to wear multiple times across a weekend, which helps to keep your packing light.

I rounded up more of my favorite pairs of jeans I can’t wait to pull out this Fall here!

10. Sweater Dress

When you just want to reach for one item that feels feminine and put together, a sweater dress is the way to go. It’s cozy, chic and there are so many way to style one. Pair it with ankle boots for dinner, or wear it with lug sole boots and a field jacket during the day.

A midi length style sweater dress is particularly versatile since you can layer tights underneath if the weather turns colder. This fringed sweater dress and this rib knit number would also be great options.

11. Cashmere Wrap

For years I’ve called this cashmere wrap my travel MVP. It’s the piece that does everything — it’s a scarf, it’s a blanket for the car or train, it’s an extra layer for a chilly evening, and it instantly makes an outfit look elevated.

On a cozy weekend trip, it’s especially handy. Drape it over your shoulders while sipping wine by the fire, or wear it on the journey home when you want to be comfortably. I never travel without one! This is another great option.

12. Bucket Bag

When it comes to accessories, I suggest keeping things simple. Opt for a structured and surprisingly versatile suede bucket tote

It can hold all your weekend essentials (sunglasses, scarf, small makeup bag, etc.) without looking bulky, and it transitions seamlessly from day to night. If you’re looking to make an investment in your handbag collection, this would be my pick!

Weekend Getaway Packing List: Cozy Fall Outfit Ideas

Wit Whimsy wearing Varley pullover and pants.

This Varley pullover and these Varley pants are favorites of mine. Comfy yet put together. Wearing a M in both.

 Weekend Getaway Packing List: Vouri Vest

This Vuori vest (size M).

J.Crew Fall Outfit : plaid and suede

Plaid and suede as a combo in Fall forever. Shop this look HERE.

Jenni Kayne Saturday Set

The most perfect comfy yet elevated sweatset for weekend getaway lounging, the Jenni Kayne Saturday Sweatshirt + Saturday Sweatpants. Use code MEGHANDONO10 for 10% off your order.

Weekend Getaway Packing List: cashmere half zip from Jenni Kayne

This cashmere half zip from Jenni Kayne that was one of my most worn (oh so cozy!) sweaters of the last few winters. Size M. I have recently added the gorgeous ivory to my collection, too. Use code MEGHANDONO10 for 10% off your order.

Wit Whimsy wearing Jenni Kayne Evertday Sweater.

The Jenni Kayne Evertday Sweater is such a good year-round sweater. It’s lightweight but still cozy and features edge detailing on the bottom hem and sleeves. Use code MEGHANDONO10 for 10% off your order.

Freda Salvador Boot Fall Outfit

Water resistant suede? Yes please! These Freda Salvador boots are so lightweight making them perfect for travel and oh so practical. Super comfy, too. I wear my true size. Use code WITWHIMSY10 for 10% off your first Freda order!

. . .

What Should Be Your Weekend Getaway Packing List?

When it comes to packing for a cozy Fall weekend getaway, having a smart weekend getaway packing list ensure comfort and versatility are key! Opt for neutral colors and classic silhouettes, and don’t forget to have fun!

Shop Cozy Weekend Getaway Packing List

 

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