Casual Weekend Away Outfits: Must-Haves

Wednesday, December 21, 2022
Casual Weekend Away Outfits: Must-Haves

If you’re like the 70% of Americans who work Monday through Friday,1 the weekend might be your only free block of time for traveling. Weekends away can be wonderful for clearing your mind, exploring a new place, and collecting some much-deserved “me time.”

No matter what destiny has in store for your weekend away, packing the right clothing is essential. Where versatility is just as paramount as comfort, the challenge becomes choosing the right pieces for casual wear—and then fitting them into one suitcase.

We’ve got you covered (literally) with our guide to casual weekend away outfits that move with you anywhere and everywhere. We’ll dole out some go-to outfit ideas, essential must-haves, and tips for stress-free packing for your next weekend adventure. And while you’re at it, check out our airport outfit ideas and travel jersey collection so you can travel in style to your weekend getaway.

Casual Weekend Away Outfit Ideas

First thing’s first: Let’s set you up with a few no-fail weekend getaway outfits that feel casual yet put-together. We’ll aim for comfort, style, and using items you’ll likely already have in your wardrobe.

#1 Turtleneck Sweater and Denim Jacket

This cozy Turtleneck sweater is one of our top-rated styles—and we think it’s going to be one of yours, too. It’s the picture of versatility and one of our favorite picks for travel outfits.

The turtleneck sweater is sophisticated enough to dress up for dinner. Or, if you’re enjoying a night in with room service, enjoy its soft, cozy feel paired with leggings or joggers.

Our favorite way to style it? Throw a denim jacket over the top and explore the town. The wool and spandex blend makes it breathable enough for warmer temperatures and protective enough for cooler ones.

#2 Sheer Sleeve Dress and Funnel Neck Jacket

Both of these pieces are great for casual wear and can be paired with endless other outfits on their own, but together, they create a look that’s clean, elevated, and ready for a dazzling night of enjoyment.

The Sheer Sleeve Dress is just as comfortable as it is chic. No more riding up or bunching, either—it’s crafted with soft jersey knit fabric for comfortable, all-night wear.

To complete the look for a dinner or glass of wine on the town, throw over the Funnel Neck Jacket in sophisticated herringbone. Bonus: This jacket goes just as well with the stretchy boyfriend jeans or leather leggings you packed for tomorrow’s brunch.

#3 Poof Sleeve Turtleneck and Bias Cut Midi Skirt

You can’t enter a room in this casual outfit and not turn heads. The combination of the feminine floral pattern on the skirt and the pop of red in the turtleneck transition seamlessly from daytime activities to nighttime.

Wear the Poof Sleeve Turtleneck and Bias Cut Midi Skirt to:

  • A gorgeous, plant-filled cafe for a flaky croissant with a good book on the side
  • An afternoon of shopping, complete with treating yourself at the apothecary
  • Lunch at a chic tapas bar to meet up with friends in the area (cue the wine!)
  • Clinking cocktail glasses at happy hour (which is every hour on this vacation)
Casual Weekend Away Outfits

Outfit Essentials for Every Weather Type

From escaping to snow-capped mountains to sampling wine in sunny Napa Valley, your destination helps decide your wardrobe. For tips on how to pack for your destination, we’ll walk you through three potential weekends away and showcase our favorite winter wardrobe essentials for snow, rain, and sun.

For the Snow: Cozy Mountain Retreat

Hot toddies around the fire can put anyone in a festive mood. Don’t let packing for the cold weather damper it! If it feels like your coziest, puffiest sweaters are taking up more space in your bag than you’d like them to, prioritize these cute cold weather outfits for a weekend away:

#1 A Warm Coat

A warm outer layer can make or break a snowy trip. A neutral-toned sherpa coat can add warmth to any look without sacrificing comfort.

Any chance of sleet? Go for something waterproof, like a puffer jacket. If it’s too bulky to fit in your bag, consider wearing it on the plane. You’ll thank yourself later when you’re admiring the winter wonderland without shivering.

#2 A Cute Hat

We lose roughly the same amount of our body heat through our head as we do from our arms or legs.2 You wouldn’t go out in the snow with bare legs or arms, so make sure your head gets the same toasty love and care. Or if you’re traveling somewhere warm, you can’t go wrong with the Panama Straw Hat to help keep you cool. Plus, hats can:

  • Add a pop of color to neutral outerwear
  • Be packed easily in a suitcase, backpack, or duffle bag
  • Elevate any outdoor look and pull your casual outfit together

#3 A Comfy Sweater Dress

For those occasions where you’re grabbing a cider at the local lounge or visiting friends at a neighboring cabin, you might want something that still feels cozy without bundling you up like a marshmallow. Enter: The sweater dress.

Comfortable but warmer than your average cocktail dress, a knitted sweater dress brings your look effortless, flattering winter flair. Simply throw it on over some tights, add your favorite necklace, and you’re ready to go.

For the Rain: Soundside Escape

While often overcast and rainy in the winter, you might be surprised at how light the rainfall by Puget Sound actually is: The Cascade and Olympic mountain ranges protect the region from harsh weather, so it mostly only experiences light misting.3

If you love the rain but hate getting soaked, the Pacific Northwest might be for you. Here’s what you should bring for a rainy vacation (besides an umbrella, of course):

#1 A Stellar Raincoat

Although it’s unlikely to downpour by the Sound, you should still be prepared for damp days. A water-resistant outer layer, like a windbreaker or quilted jacket, will likely do the trick.

If your destination experiences harsher rain than the PNW (think Scotland or South America), you’ll definitely want to make high-quality rainwear a priority. Invest in a well-made waterproof coat that’s long enough to cover your thighs.

A good raincoat could make the difference between remembering the trip or remembering the weather.

#2 Neutral Sweaters

A simple, neutral sweater offers an enormous amount of versatility. Perfect for layering or as a standalone look, a cable-knit sweater can take you indoors and out, from a hike up Mount St. Helens to a party downtown.

Luckily for you, we’re in the business of designing comfortable, cute sweaters like:

#3 Mother of Pearl

If you’re looking for jewelry to match your PNW-inspired styles, pearl is the gem of choice. The iridescent, luminous pearls will glow even on cloudy, sunless days. Their neutral tone means they can complement any outfit, and as a marine gemstone, they’re the perfect touch to give your look a coastal feel. As a bonus, one of Portland’s main shopping neighborhoods is called the Pearl District, so you’d be right on the theme!

Casual Weekend Away Outfits

For the Sun: Napa Valley Wine-Tasting

A classic weekend getaway, wine-tasting at California vineyards offers you sunny weather, sophisticated charm, and a culinary experience like no other. Where else can you float over the landscape in a hot air balloon, taste test world-class wines, and visit a castle (yes, an actual castle) all in one weekend?

Before you take in the historic walking tours and California cabs, here’s what to pack for a trip where you’ll be spending long days in the sunshine:

#1 A Protective Sunhat

When touring Napa Valley, you’ll likely spend hours outdoors on sunny days. Spare your face the UV rays with a wide-brim hat that’s both stylish and functional. The natural tone of raffia matches all outfit colors, so it’s a perfect travel hat material for any sunny locale.

#2 A Breezy Shirtdress

Light and airy, a mid-length shirt dress fit right in at the valley. We also have beautiful boho dresses for women. The Blouson Sleeve Shirtdress makes an easy standalone piece, allowing you to go for something bold without worrying too much about matching. Whether your sun-soaked trip is to Napa, the high desert, or the Golden coast, that breezy fabric can also help keep you cool on warmer days.

When the sun goes down, layer your dress with:

#3 The Right Bag

Wine-tasting is a task that requires free hands. If you need to carry around your essentials without worrying about a purse sliding down your arm, a cross-body bag can do the trick.

Going on an all-day walking tour? Try the handy Weekend Tote Bag to cart around everything you need for the entire day. Their ability to hold bulkier items like towels and lunches makes them irreplaceable on beach or picnic trips.

Last-Minute Tips for Your Weekend Away

If staring at your empty suitcase is giving you pre-travel jitters, it might help to keep these simple tips in mind before you start tearing clothes off the hangers:

  • Plan, Don’t Overpack - While it’s great to be prepared, it’s less fun lugging around a too-big bag around an airport. A weekend trip usually takes about two full days. For such a short excursion, you can likely plan out your activities to the letter and know exactly what you need to bring, so you can only bring what you need.
  • When Versatility is Key - Unsure what the weekend will hold? Avoid packing too many items that can only be worn for one situation. Instead, try to organize your outfits around basics that can be worn in multiple situations, so you can be ready for anything without bringing your entire wardrobe.
  • Use a Color Scheme - One way to get more mileage out of your items is to plan a color scheme as you pack. This ensures that everything already matches, giving you more outfits per item and a lot fewer headaches each morning. Consider sticking to neutrals for outerwear and any item that you’ll likely use every day.
  • Layer Up - Weather report keeps changing? Rather than packing a bulky coat just as a precaution, you might try packing multiple layers of sweaters, flannels, and thermals that can be worn on their own if the weather turns out to be warmer.
  • Go Wrinkle-Free - Aim to pack fabrics that will minimize your risk of wrinkling. Wool makes a great choice for wrinkle-free winterwear, as does cashmere. Synthetics like nylon and polyester can also resist creasing.
  • If you’re married to your linen slacks or trousers, don’t fret— rolling items instead of folding them can also help keep them looking polished and professional during their journey in your suitcase.

    Ready to pack your bag? Check out our vacation-style collection to find a comfortable and fashionable outfit that speaks to you.

    Weekend Travel in Style with Karen Kane

    Wherever the road takes you, feel ready with a wardrobe from Karen Kane. From beach-print tees to cozy twist-front tops, our styles bridge the gap between timeless and modern, bringing you an effortless chic that’s as easy to wear as it is on the eyes.

    And that’s one thing that all casual weekend away outfits should be: effortless. From our comfortable dresses to our luxuriously creamy sweaters, we believe that true sophistication doesn’t need to come from an overpacked suitcase and uncomfortable clothes that you can’t wait to take off.

    For classics to suit your next weekend's getaway, shop now.


    1. U.S. Bureau of Labor Statistics. Percent of employed people who worked by day of week.
    2. Cleveland Clinic. Do You Really Lose Most of Your Body’s Heat from Your Head?
    3. The Seattle Times. Why are raindrops smaller in Seattle? How do the mountains affect Puget Sound weather? Your rain questions, answered.
    Prev Next