15 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 13 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

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 elevated by a line of shiny gold buttons sewn up the front.

Siliteelon Striped Button-down Shirt

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 is 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

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

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

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

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 for with polos, knits, or even cropped jackets.

Amszke Vegan Leather Saddle Bag

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

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

A quilted vest shines during travel, especially in the fall and winter months. More than 30,000 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 $33, it’s a steal well worth a place in your shopping cart.

Amazon Essentials Short-sleeve Polo Shirt

No preppy round-up would be complete without a classic polo, and this one from Amazon Essentials is just $13. It’s lightweight, easy to layer, and comes in a range of colors for everyday wear. Best of all, it’s versatile. Pair it with a pair of jeans and sneakers for a more casual vibe, or dress it up by tucking it into a skirt or trousers. You can even layer it under your favorite sweatshirt to elevate your lounge look on long travel days—the options are endless.

Project Cloud Memory Foam Boat Shoes

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

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

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.

Love a great deal? Sign up for our T+L Recommends newsletter and we’ll send you our favorite travel products each week.