How to Kill It in the Photos for a Weekend Getaway Without Overpacking

Packing for a weekend getaway

Hi everyone! Today I’m explaining how to pack a bag for a fun fall weekend trip, whether it’s a romantic getaway, a girls’ weekend, or an excursion to meet up with college friends.

I pack way more than I need on weekend trips to have a contingency plan for anything: heat, cold, a workout, or even a SECOND workout (Note: I haven’t ever worked out more than once on a weekend trip). I also struggle to find a correctly sized bag—I either stuff everything into a backpack or overpack in a too-large duffle.

In the past year of adult life, I’ve fine-tuned my weekend packing routine to leave on Friday night after work and come back on Sunday. Based on that experience, here’s my guide to packing perfectly for your weekend getaway!

Step 1: The Bag

Modern, sleek roller bags are all over the ads on my Instagram feed right now, but as someone who once packed a duffle bag for a ten-day trip to Europe, I’m against roller bags. Even if you don’t have to haul your bag through airport security, you don’t need to bring that much with you, especially for a weekend trip.

Do pack in a large backpack, a duffel bag, or any other medium sized bag you can carry. The Madewell weekend bag I’ve been drooling over is here but I’ve used my sturdy L.L. Bean duffel for years now.

Step 2: The Clothes

On Top:

  • Tank top
  • Printed sweatshirt
  • Medium-weight sweater in a fall color
  • Bodysuit in black or gray

On the Bottom:

  • Athletic leggings
  • Light-wash skinny jeans
  • Denim button-front skirt

On Your Feet:

  • Running shoes
  • Canvas sneakers
  • Suede boots

Everything Else:

  • Denim jacket
  • Off-the-shoulder dress
  • Suede clutch
  • Plaid infinity scarf
  • Gold necklaces: one long, one short
  • Bras, panties, sleepwear, socks

Step 3: Packing

It’s Friday morning, you’re leaving straight from work for Charleston/Nashville/Richmond, and your bag is empty. Don’t stress—throw the first travel outfit in your backseat to change into after work, then put the other two pairs of shoes on the bottom of your bag, soles together. Slide the necklaces into the clutch. Pack the rest of the clothes rolled if you’re using a backpack or folded for a duffel. Toss in your toiletry bag and go!

Step 4: Putting It All Together

Travel Outfit Friday

CC takes DC travel outfit

Change out of your work clothes into your tank top, athletic leggings, running shoes, and sweater. This layered travel outfit will keep you comfortable for airplane travel or an over air-conditioned car ride.

Dinner and Drinks Friday

CC takes DC dinner and drinks outfit

When you get there, put on your off-the-shoulder dress, short necklace, Converses, and denim jacket. If your hair has suffered from the dehumidifying effects of air travel or you woke up too late to blow dry (#Friday) put it up in a topknot.

Saturday Museum Exploring, Wine Tasting, and Local Flavor

weekend exploring outfit

Wear the same sweater you wore yesterday, loosely tucked into your button-front skirt, with the scarf and denim jacket if it’s chilly. These flat suede boots are great for walking so you won’t miss anything your weekend locale has to offer. If you’re visiting a historical site or doing anything else too strenuous to wear a skirt, you can always switch out the skirt for cuffed skinny jeans.

Saturday Night Fever

Going out outfit

Whether you’re partying with boo, trying to get a Charlestonian’s number or just living it up with your girls, break out the bodysuit with the same skirt and boots you wore during the day. A weekend away is a great time to wear something bold—I live in fear of seeing my boss while I’m out on a Saturday night!

Sunday Morning Run

Wear your leggings, running shoes, and tank top if you’re inspired to work out Sunday morning, or for a hike on a cool local trail.

Sunday Brunch and Travel Home

Packing for a weekend getaway

To go straight from brunch to the flight back, put on the printed sweatshirt, skinny jeans, and Converses. To keep these basics from being boring, toss on both necklaces and your denim jacket. I love double denim, but if you’re new to the Canadian tuxedo you can ease in with dissimilar washes.

Step 5: Love these outfit ideas but no clue where to go?

Relatively close to DC, I personally recommend Staunton, Charlottesville, and Richmond. If you’re willing to hop on a plane then Charlotte, Charleston, Nashville, New York, and Boston are within weekending distance.

Where is your favorite weekend vacation spot for fall? Would these outfits work for you? Let me know in the comments.

3 thoughts on “How to Kill It in the Photos for a Weekend Getaway Without Overpacking

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