14 Best Preppy Fall Travel Outfits at Amazon

Prep is back—just in time for fall flights and weekend leaf-peeping getaways. According to Pinterest’s 2025 Fall Trends Report, searches for preppy staples are skyrocketing as folks embrace this polished aesthetic. From breezy button-downs and plaid skirts to cozier staples like striped cardigans and chunky cable-knit sweaters, dressing like you went to a New England prep school is in—even if you’ve never stepped foot in New England.

Luckily for our suitcases, the prep aesthetic leans into comfortable, reliable staples that feel put together, no matter how you mix and match them. Even luckier, a well-rounded preppy wardrobe doesn’t have to break the bank. We’ve found 14 travel-ready Amazon styles that look great, without the designer price tag. These pieces are timeless, practical, and ready for wherever your next trip takes you.

Preppy Fall Travel Essentials

Lillusory Striped Cardigan Sweater

Amazon

A striped cardigan is another timeless staple, and this one from Lillusory is worth shopping. The slightly oversized cut keeps it comfy, perfect for throwing on over tank tops and T-shirts. And you won’t overheat—the knit is soft and breathable. Choose from solids or stripes in a palette of traditional colors, like dark red, navy, cream, and tan, each accented by a line of shiny gold buttons sewn up the front.

Siliteelon Striped Button-down Shirt

Amazon

Short on packing space? Don’t underestimate the power of a quality button-down. This one from Siliteelon is a budget-friendly buy that can bolster any capsule wardrobe; wear it open over a swimsuit at the beach, tuck it into trousers for dinner, or layer it under a sweater vest when the weather cools. It’s lightweight enough to stay cool in warm destinations, and a perfect layer to tie around your shoulders or waist in case the weather dips. Trust us—it earns space in your suitcase every time.

Hyipels Knit Cropped Sweater Vest

Amazon

If you really want to put on the prep this fall, get a sweater vest. This one is just $25 and comes in as many cute colors and patterns as you can dream of: scholarly argyles, iconic stripes, cheeky checkerboards, even florals and hearts. The boxy, sleeveless fit makes it easy to toss on over just about anything. It’s less bulky than traditional cable knits or chunky cardigans, so you won’t lose space in your carry-on bag.

Beauseen Classic Leather Penny Loafers

Amazon

Penny loafers never go out of style, and this buttery leather pair offers a luxe look at an unbeatable price. The slip-on design makes them ideal for walking through airport security, while the cushioned sole is comfortable enough for hours on your feet. They’re versatile, too, and can transition seamlessly from casual brunch and a wander around the museum, to dressed-up dinners and late-night cocktails—all for less than $50.

Dokotoo Cable Knit Quarter-zip Pullover

Amazon

Warm but not bulky, this cozy cable knit pullover works just as well bundled over a T-shirt during a chilly plane ride as it does tied around your waist at lunch. The ribbed detailing gives it extra polish, while the zip makes it easy to adjust in changing temps. For a piece that feels straight out of the country club, this is the one.

Idealsanxun Wool Plaid Mini Skirt

Amazon

Plaid skirts are prep-school core, but this one feels grown-up, with its structured cut and warm wool blend. It’s an easy pack-and-wear option for city trips when you want to look more pulled together. For true scholastic style, pair it with penny loafers or Mary Janes. As for a top, the high waist makes it versatile enough with polos, knits, or even cropped jackets.

Amszke Vegan Leather Saddle Bag

Amazon

Structured and understated, this vegan leather saddle bag channels the equestrian roots of classic prep style. The removable straps let you wear it crossbody-style during the day for hands-free exploring, then switch to a shoulder bag for dinner or drinks. There’s plenty of room for your travel essentials, too, so you won’t have to worry about leaving anything behind.

Micoson Cable Knit V-neck Pullover

Amazon

With temperatures dipping, it’s high time for warmer layers. Enter this perfect cable knit pullover that looks as good as it feels. Part sweater and part polo, it styles wonderfully layered under a puffer vest, tied around your shoulders, or on its own. The varsity-inspired striped collar and cuffs look like something out of an Ivy League university—you’ll never want to take it off.

Fuinloth Quilted Vest

Amazon

A quilted vest shines during travel, especially in the fall and winter months. Amazon shoppers love the Fuinloth Quilted Vest for its warmth and packability; you can squeeze it down into a duffel or backpack without it weighing you down. At just $32, it’s a steal well worth a place in your shopping cart.

Project Cloud Memory Foam Boat Shoes

Amazon

Friendly reminder: you can wear boat shoes, even if you don’t own a boat. This pair from Project Cloud makes great travel shoes: the slip-on style is convenient for airport security, the memory foam keeps your feet comfy, and they’re water-resistant, so they’ll keep you dry in case of drizzle. For a shoe that truly multitasks on vacation, this is the one.

Anyzsco Bow-tie Baseball Cap

Amazon

If you’d rather not do your hair at all, this adorable baseball cap is for you. The chic, minimalist bow print gives it a preppy twist that looks great on long plane rides, road trips, and everywhere in between. Bonus: It doubles as sun protection, so if you’re going somewhere tropical or just want the sun out of your eyes, it’s got you covered (literally).

Hhqqwz Quilted Makeup Bag

Amazon

Has your toiletry bag seen better days? Nab this charming bag, which comes in all sorts of coquettish florals and prints that flawlessly fit the aesthetic. Even better, its quilted body makes it easy to stuff into suitcases and overstuffed weekenders. If something spills, no problem—just pop it in the wash.

Sidefeel Wide-leg Corduroy Pull-on Trousers

Amazon

A pair of trousers is an easy way to keep your outfit feeling preppy, and these corduroy bottoms elevate your look with their tailored, put-together style. The corduroy texture adds intrigue while the stretchy waistband ensures you’ll be comfy from day to night.

Yogipace Cropped Pull-On Dress Pants

Amazon

Form-fitting, classic-hued pants like these pull-on pointe pants from Yogipace elongate your frame while reinforcing the preppy trends nod to elevated silhouettes and timeless colors. Pair them with a polo top for casual days, a fitted jacket for outings, and your favorite blouse when you want to dress them up.

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