11 Outfit Ideas To Try This Weekend

Ditch the leggings and sweatpants and try these fun alternatives instead!

With the end of summer upon us, ditch your usual Saturday routines of reading a newspaper over coffee or dusting in your jammies and instead do something adventurous. Grab your cat, pack your favorite dresses into a bag, and rent a car with nothing but a map and the idea of driving until you run out of gas. Who knows where you could go? Will you head south for some brassy blues and bread pudding,  or north for an excuse to wear a sweater and order the first hot chocolate of the season? Or go somewhere obscure with no plan in mind and stumble upon the world's biggest ball of twine? The possibilities are endless.

And so are the outfit choices. Just as important as the playlist, your day trip outfits help tell the story of your adventure. So instead of going with the usual sweat pants and tee combo that feels second nature when beef jerky and drive through food is involved, why don't you try something with a little more of a story? Below are eleven comfortable and creative outfits to wear on your road trip- hop into them and let the memories begin!

1. The Belted Maxi Dress Look

The reason so many of us go with leggings when embarking on a ten hour car ride is because they feel like the next thing to pajamas: Comfort central. But do you know what's equally as cozy and unrestricting? A loose and baggy maxi. Pair it with minimalist sandals for a clean-lined look, and cinch it at the waist if you want a more defined silhouette. You can always take it off after you open that second bag of crisps...

2. The Culottes Look

Pick a pair of wide leg culottes (or a midi skirt if you haven't hopped onto the trend) and match it with a racer back crop top. The fresh cut of the top will make the simple outfit feel a little more interesting, and then continue to elevate the look with statement sandals and metal shades. 

3. The Leather Jacket Look

What is it about a leather jacket that allows you to wear it with the same nonchalant air whether you're going to a password-only speakeasy bar in Chicago, or getting bagels Sunday morning at the bodega down the street? Give a simple look of jeans or tailored sweats a touch of casual polish by pairing them with a leather jacket and sneakers. Instant cool. 

4. The Denim Pinafore Look

Who could possibly be uncomfortable in a roomy pinafore? To keep it simple and unfussy, pair it with a white collared shirt. To keep it inspired and interesting, pair it with statement shoes like tied booties, gladiator sandals, or blocked heels. The on-trend feel of the shoes will keep the mood of your sweet pinafore looking less school yard and more retro chic.

5. The Cargo Jacket Look

The best outfits are those that look complicated when they're really achieved in three steps or less. Grab yourself a pair of jeans, a striped shirt, and a pair of penny loafers that will give your look a touch of old-school gentleman charm, and top it all off with a baggy cargo jacket. The jacket not only will add a touch of color, but will add its weight in proportions by dragging the eye downward. Simple, chic, and perfect for any linoleum-seated diner you pull over for from the interstate. 

6. The Baggy-On-Baggy Look

Grab yourself a pair of wide leg pants or a free flowing maxi skirt and pair it with the baggiest chambray top you have in your collection. Roll the sleeves, tuck in only half the hem, and be prepared to give off a stylishly disheveled vibe. 

7. The Accent Scarf Look

Chances are you were planning to wear jeans and a striped tee for your weekend getaway, or some version of that. Give your simple look a pop of fun by tying a handkerchief or silk scarf all French-like and sassily-skeltered around your neck. Instant personality. Add in black sunglasses and you'll look like a mysterious woman with a handful of stories on the road. Is she running from something, maybe looking to start over in a new state where magnolia trees grow, or does she just have an adventurous heart? Who knows. But dang does she look amazing. 

8. The Layered Summer Dress Look

Give a loose dress you love a new life by layering a boxy crop top over it. It'll be loose around your legs as you drive passed gas stations and mountains on your map, and just roomy enough to keep you comfy until the next rest stop. 

9. The Crop Top Sweater Look

Grab your favorite babydoll cotton dress, pull on your most worn-in black boots, and slip on a short-hemmed sweater over your head and get ready to sing some Alabama Shakes as you hit the open road. It's unfussy, cozy, and you get bonus points for fun if you add in a wide brimmed hat to keep your hair in place as you leave the car windows down.

10. The Overalls Look

If you were planning on wearing denim this weekend, you might as well go all the way. Take your favorite (or only) pair of overalls and go in more of an uptown-girl route rather than an artist-in-her-studio direction by styling the dark blue with a prim button down and classic flats. Get cheeky with your accessories by adding a bow to your hair or adding dangling statement earrings to give it that last feminine touch.

11. The Denim Jacket Look

Instead of going the usual route and putting your denim jacket on your back, tie it around your waist. It looks amazing with a t-shirt or shift dress and gives you that laid-back Weekenders vibe. 

Marlen Komar is a writer living in Chicago with a penchant for mom jeans and kimchi tacos, and primarily writes about fashion history. She has bylines in Bustle, CNN Style, Racked, Allure, Curbed, and Apartment Therapy, and rarely stays in one place too long as she travels for most of the year. Website: marlenkomar.com