14 Best Amazon Fall Travel Essentials and Outfits

Every year when Labor Day rolls around and end-of-summer sales start, I make seasonal upgrades to my travel gear to prepare for fall trips. That means swapping my breezy linen for cozy layers, sandals for sneakers, and sundresses for sweaters. Mostly, I stick to classic travel clothing pieces instead of trendy ones so they can stay in my closet year after year.

If you’re in fall travel mode like I am, it’s time to get organized. From comfortable white leather sneakers to a flannel shacket that will polish any look, here are my smart swaps for your summer go-tos that won’t break the bank. After all, apple-picking, leaf-peeping, and rainy city walks with hot coffee in hand are just around the corner.

Best Fall Travel Wardrobe Essentials

Retire: Oversized white button-ups

Replace With: Flannel shackets

Around this time each year, I pack up my oversized white button-up that I wore over swimsuits and shorts in favor of a trusty flannel shacket. It’s the same idea—a layer you can throw over just about anything in your closet—but it adds a layer of warmth instead of allowing the summer breeze to flow through.

I’ve owned this classic flannel shacket for two years now, and it fits right in whether leaf-peeping at home in New England or cozying up to a campfire. I particularly love that the neutrals pair seamlessly with my travel wardrobe. For those who want something a bit more on-trend, consider a piece like this brown suede shacket, an elevated, polished version of that cozy flannel.

Retire: Sandals

Replace With: White leather sneakers

Unless I’m headed to a tropical destination, I say goodbye to my sandals in favor of comfortable closed-toe shoes. I’m particularly loving my Kizik Vegas 2 sneakers, a true travel M.V.P. Because of hands-free technology in the heel, you can step into them without having to bend down and pull the heel back (great news if you’re perpetually juggling your bags and a coffee before heading out the door).

I recently wore them straight from the box on a trip to France with a 10-hour travel day and had no pain, so I can attest that they’re worth the splurge—plus, they match everything from dresses to midi skirts to black pants. If the price tag is a bit much, you can get the same look for less with these white faux leather Adidas sneakers.

Retire: White linen pants

Replace With: Black ponte pants

When fall arrives, summer fabrics like linen are the first to exit my rotation. I replace them with a heavy yet comfortable fabric like ponte, which is both stretchy and wrinkle-resistant—two major bonuses when you’re facing all-day travel. I’m eyeing this pair of black ponte pants, which looks polished and sleek like pants three times the price. It’s a classic look to wear again and again.

Retire: Tennis dresses

Replace With: Oversized sweaters and bike shorts

If you’re anything like me, your unofficial uniform for summer was a tennis dress—easy to throw on and super comfy. The fall version of that no-effort athletic look is the oversized sweater and bike shorts (a.k.a. the Princess Diana look). It’s the perfect outfit for transitional weather when it’s brisk in the morning but warm in the afternoon—just peel off the sweater and you’re ready for those last summer rays. Bonus if the shorts have a pocket for your phone, like this Baleaf pair that comes in different lengths.

Retire: Quick-dry hiking joggers

Replace With: Fleece-lined sweatpants

I’ve written extensively about how much I love these quick-dry joggers that keep me cool and dry on summer hikes (they even made it into my capsule wardrobe). But when it comes time for fall, I start thinking about what’s going to keep me warm if I’m out all day exploring. When I went to Iceland in September, for example, I wore these fleece-lined sweatpants. They took the chill right out of the air—and then I kept them on all winter in Boston, too.

Retire: UPF sun shirts

Replace With: Lightweight sweaters

I always pack a UPF shirt for sun protection in the summer, but when the light starts to fade, that spot in my suitcase goes to the perfect lightweight sweater that I can layer over button-ups or tie around my shoulders. I’ve got my eye on this striped one at Amazon that’s only $11. The style will add dimension to my outfit yet still coordinate with my neutrals, but it also comes in several fall-ready colors like burgundy and olive.

Retire: Sundresses

Replace With: Versatile coats

Yes, I get a little sad packing up my sundresses every year, but it’s time to start thinking of crisp, drizzly days ahead. Depending on what you’ve got on the itinerary, I recommend a raincoat for active adventures and hikes (this highly rated Columbia rain jacket won’t steer you wrong), or a long wind- and water-resistant trench coat for a more fashion-forward yet practical city look.

Retire: Matching linen sets

Replace With: Matching sweater sets

A matching set goes a long way in maximizing your looks for carry-on-only travel (especially if you’re trying to create multiple combos with the 3-3-3 packing method). Now is the perfect opportunity to upgrade your flowy, summery matching set for a cozier one that will take you from flight to fireside. This matching set from Amazon is effortlessly stylish but has some cool features that stand out together or alone, like a crewneck sweater and wide-leg sweatpants.

Retire: Straw totes

Replace With: Leather crossbody phone purses

Goodbye, beach bag, and hello, leather crossbody that will seamlessly take you from walking tour to fall wedding. This style is especially great for travelers because it’s small enough to stuff in a carry-on and has anti-theft features such as RFID-blocking technology and slash-proof straps that help keep your valuables secure when you’re on the go.

If you like the look but not the price tag, you can get the same style and security features for even less in a faux-leather version from Inicat—and don’t forget a clear version for stadium events like concerts and football games.

Retire: Braided flats

Replace With: Ballet flats

Once you’ve got your fall walking sneakers covered, you’ll need a pair of flats or loafers to wear for dressy dinners or evening shows to replace the cute braided sandals or braided Huarache loafers you rocked all summer. I swear by my comfy Vivaia ballet flats, but you can snag a similar look for less with this pointed-toe version with a memory foam insole at Amazon for just $33.

Retire: Swim cover-ups

Replace With: Long cardigans

With summer beach trips mostly in the rearview, it’s time to trade light swim cover-ups for chunkier cardigans. A must for fall, no matter where you’re headed (think: apple-picking, beach bonfires, boat rides, morning city walks; the list goes on), this staple will keep you warm over shirts and dresses until you need to shed a layer. I love the slouchy look of the Lillusory Cardigan, which reminds me of a tan one I purchased last year that’s permanently a favorite of mine.

Retire: Mini skirts

Replace With: Midi skirts

While nothing is stopping you from wearing your favorite summer mini skirt with tights into fall, I prefer to switch to a midi skirt for more coverage. Plus, the midi length looks great with fall staples like leather or bomber jackets and boots or court sneakers of any kind. I like the look of this mesh midi skirt at Amazon that can be easily packed into almost nothing. You could also sneak some fleece-lined leggings underneath as the weather gets colder.

Retire: Wide-brimmed straw hats

Replace With: Baseball caps

Sure, there’s far less direct sun than in summer, but UV rays still break through clouds in the fall, and it’s important to protect your eyes. I’m taking the new season as a chance to upgrade my old baseball cap with a wear-with-everything style like this one at Amazon. In addition to protecting my eyes and face on days out and about, I also love a cap because it can conceal messy airplane hair.

Retire: Portable fans

Replace With: Foldable umbrellas

Don’t forget to upgrade your go-to accessories this fall. If you have a favorite portable fan in your carry-on or purse, now’s a great time to replace it with a compact, foldable umbrella. You’ll barely know this 11-by-2.75-inch one is there, but you’ll be glad it is once you’re caught in a downpour on the road.

This one also caught my eye because the brand says it was tested in a 70-MPH wind tunnel, which is the kind of sturdy construction I’m looking for in any umbrella. If you’ve ever walked around New York City with a flimsy umbrella that’s been turned inside-out by the wind, you know why.

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