What To Wear For A Fall Weekend Getaway

I love a great weekend trip and I try my best to swing them as much as possible. In fact, I’ve been thinking about writing a whole post on the topic of how to travel often with a full-time job. Stay tuned for that! Whenever I take a weekend trip, I carry on my suitcase for ease and speed and because I don’t need to pack that much. Fall is one of my favorite times of the year to travel because I love searching for fall leaves and I love hopping around the country to attend fall events like football games. This past weekend, I had the best time in Oxford, Mississippi for the Ole Miss Alabama game. I also have a few more fall trips coming down the pipe to Georgia, Colorado, and Vancouver so I thought I’d write a post on what to wear for a fall weekend getaway.

For me, being comfortable while traveling is key. At the start of the fall season, I travel in flats because they are comfy and keep my feet covered so I’m not chilly. I also love traveling in ballet flats because I usually find myself wearing them with another outfit once I arrive at my destination and because flats are stylish enough that they can easily be worn out if I head somewhere straight from the airport. I’ve had these J.Crew flats for years. I wear them to work and wear them in my everyday life, as seen in this post. I also really like these flats for fall and I have to mention that Nordstrom has a great selection of ballet flats right now. After hearing over and over again that the Chloé scallop flats are the most comfortable flats around, I finally saved a little from a few paychecks and ordered them last week! So excited!

There’s nothing I hate more than freezing to death on an airplane so I always travel in jeans in the fall. I wear a lot of blue jeans but I also wear white jeans because it’s fun to mix up my look and because, even though I fully believe in wearing white after Labor Day, it’s still a (fun) surprise for people to see white jeans around. You’ve heard me mention it before but these J.Crew white skinny jeans are my all time favorite pair.

How adorable is this pale blue sweater (it also comes in black and grey). I absolutely can’t get enough of the bows in the back. I always bring a sweater when I travel so I can stay warm on planes. I’m also your ultimate jeans and a sweater girl in the fall so I would definitely plan to wear this sweater on the plane and then wear it straight out to dinner from the airport. It’s a great cozy and practical yet chic piece to add to your closet! I’d also wear this sweater to work with a tee under it.

When I travel with a bigger accessory like a hat or a pair of boots, I always wear them on the plane. I do this mostly because it saves room when I’m packing for things like boots and because it keeps my hats from getting crushed. I love, love hates in the fall and the winter. My black hat is classic but every now and then I like mixing in this blue hat (similar for less!) for a pop of color (you saw me wear this hat last fall here).

I snagged this duffle bag last month during the Nordstrom Anniversary Sale (I also love this duffle!). I can already tell that it’s going to be my go-to travel bag for weekend trips for the rest of the year. I love to true brown color and the soft faux leather of the bag. It’s the perfect size for 48 hours away!

My watch keeps me on track with my travel planes. Every time I look down and see this particular watch I smile because my future sister-in-law gave it to me a couple of months ago for my birthday. The company that makes this watch is called TOKYObay. They make watches in lots of different styles and colors. I’m obviously biased, but I think they make a great gift!

Sweater (also comes in black and grey) / Jeans / Duffle Bag (also love this one) / Hat (similar for less) / Flats (I also just splurged on these) / Necklace / Watch / Lip Gloss (Nars – ‘Quito’)

What To Wear For A Fall Weekend Getaway:

Photography by Valorie Darling