14 Best Preppy Fall Travel Outfits on Amazon

Prep is back on, just in time for fall flights and weekend leaf-peeping getaways. According Pinterest Fall 2025 Trends Report, Searches for preppy basics are skyrocketing as people embrace this refined aesthetic. Of windy buttons and plaid skirts to cozier staples like striped cardigans and thick cable knit sweatersDressing like you went to a New England prep school is trendy, even if you’ve never set foot in New England.

Luckily for our suitcases, the getting-ready aesthetic is all about comfortable, dependable basics that sit together, no matter how you mix and match them. Even luckier, a full preppy wardrobe doesn’t have to break the bank. We’ve found 14 travel-ready styles from Amazon that look great, without the designer price tag. These pieces are timeless, practical, and ready to go wherever your next trip takes you.

Preppy Fall Travel Essentials

Lillusory Striped Cardigan

A striped cardigan is another timeless staple and east of Lillusory It is worth buying. The slightly oversized fit keeps it comfortable, perfect for layering over tank tops and t-shirts. And you won’t overheat: the fabric is soft and breathable. Choose from solids or stripes in a traditional color palette, such as deep red, navy, cream and tan, each accented by a line of shiny gold buttons sewn to the front.

Siliteelon Striped Button Down Shirt

Short on packing space? Don’t underestimate the power of a quality buttons. This one from Siliteelon is an affordable purchase that can bolster any capsule wardrobe; Wear it open over a swimsuit at the beach, tuck it into your pants to dinner, or layer it under a sweater vest when the weather gets cold. It’s light enough to stay cool in hot destinations and a perfect layer to tie around your shoulders or waist in case the weather turns cold. Trust us: you always save space in your suitcase.

Hyipels Cropped Knit Sweater Vest

If you In fact If you want to prepare 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: erudite argyles, iconic stripes, bold checkerboards, even flowers and hearts. The sleeveless, boxy cut makes it easy to throw over almost anything. It’s less bulky than traditional cable knits or chunky cardigans, so you won’t lose space in your handbag.

Beauseen Classic Leather Penny Loafers

loafers It never goes out of style, and this buttery leather pair offers a luxurious look at an unbeatable price. The slip-on design makes them ideal for getting through airport security, while the cushioned sole is comfortable enough for hours on your feet. They’re also versatile and can seamlessly transition from casual brunch and a stroll through the museum to fine dining and late-night cocktails, all for under $50.

Dokotoo Quarter Zip Cable Knit Sweater

Warm but not bulky, this cozy cable knit sweater It works just as well layered over a t-shirt during a cold plane ride as it does tied around your waist during lunch. The ribbed detail gives it extra shine, while the zipper makes it easy to adjust in case of temperature changes. For a piece that looks like it came straight from the country club, this is the one.

Idealsanxun Checked Wool Mini Skirt

plaid skirts They’re high school staples, but this one feels grown-up, with its structured cut and warm wool blend. It’s an easy pack-and-go option for city trips when you want to look more put together. For a true school style, pair it with loafers or Merceditas. As for a top, the high waist makes it quite versatile with polos, knitwear or even short jackets.

Amszke Vegan Leather Saddle Bag

Structured and discreet, this vegan leather saddlebag Channels the equestrian roots of the classic grooming style. Removable straps let you wear it cross-body during the day for hands-free exploring, then switch to a shoulder bag for dinner or drinks. There’s also plenty of room for your travel essentials, so you won’t have to worry about leaving anything behind.

Micoson V Neck Cable Knit Sweater

With temperatures dropping, it’s time to wear warmer layers. Enter this perfect cable knit sweater That looks as good as it feels. Part sweater and part polo, it looks wonderful layered under a padded vesttied over the shoulders or alone. The college-inspired striped collar and cuffs look like they came straight from an Ivy League university—you’ll never want to take them off.

Fuinloth padded vest

A padded vest shines during travel, especially in the fall and winter months. Amazon buyers love it Fuinloth padded vest for its warmth and packability; You can put it in a duffel bag or backpack without it weighing you down. At just $32, it’s a bargain worth adding to your shopping cart.

Project Cloud Memory Foam Boat Shoes

Friendly reminder: you can Wear boat shoes, even if you don’t have a boat. This Project Cloud pair They make great shoes for traveling – the slip-on style is convenient for airport security, the memory foam keeps your feet comfortable, and they’re water resistant so they’ll keep you dry in case of a drizzle. For a shoe that will truly multitask on vacation, this is the one.

Anyzsco Bow Tie Baseball Cap

If you prefer not to comb your hair at all, this adorable baseball cap It’s for you. The sleek, minimalist bow print gives it a preppy touch that looks great on long plane rides, road trips, and everywhere in between. Bonus: It also doubles as sun protection, so if you’re going somewhere tropical or just want the sun to take your eyes off, it’s got you covered (literally).

Padded makeup bag Hhqqwz

Has your toiletry bag seen better days? catch this lovely bagwhich comes in all kinds of flirty florals and prints that fit the aesthetic perfectly. Even better, its padded body makes it easy to pack into suitcases and on crowded weekend trips. If something spills, no problem – just throw it in the washing machine.

Sidefeel Wide Leg Corduroy Pull-On Pants

A pair of pants is an easy way to keep your outfit feeling preppy, and these corduroy Enhance your look with its tailored style. The corduroy texture adds intrigue, while the elastic waist ensures you’ll be comfortable day or night.

Yogipace Pull-on Short Dress Pants

Skinny pants in classic tones like these Yogipace slip-on toe pants elongate your figure while reinforcing preppy trends that nod to elevated silhouettes and timeless colors. Pair them with a polo shirt for casual days, a fitted jacket for going out, and your favorite blouse when you want to dress them up.

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