15 Fall Travel Essentials for Shoulder Season Trips

Temperatures may be dropping, but my travel plans certainly aren’t. Fall shoulder season — September and October — is one of my favorite times of year to travel for a myriad of reasons: hotel prices drop, back-to-school obligations create less crowded streets and airplanes, and more manageable temperatures make it easier to be outdoors.  

After writing about why I love London during shoulder season, I’ll finally get to check into Raffles London at The OWO — a luxury, five-star stunner that’s just steps away from some of the city’s best landmarks. And, with London just being named the second most highly rated city in Europe for walking and cycling tours, I’ll certainly get good use out of my favorite fall travel activewear and walking shoes. Vancouver is also on my fall travel list, with a check in at Rosewood Hotel Georgia, which just reopened a few months ago to unveil new luxury rooms and culinary experiences. Lastly, I always love my former home, New York City, in the fall when humidity drops, rooftops like 1 Hotel Brooklyn Bridge are still buzzing, and popular new restaurant openings like Japanese izakaya spot Kin Gin and Northern Mexican cuisine-inspired Corima are easier to get a reservation at.

Packing may take a little more creativity in temperatures that teeter between not quite summer but not quite winter. Functional pieces that can be layered and breathable shoes are just a few of my go-tos. Luckily, Amazon has a number of options that are right on time for shoulder season. Below are 15 picks I’ll be relying on as I close out my 2024 travel plans. 

PrettyGarden 2-piece Sleeveless Tracksuit 

A comfortable two-piece outfit is always going to top my packing list for any season. This option from PrettyGarden is especially suited for shoulder season. The sleeveless top pairs well with the high-waist pants that include an elastic waistband and drawstring for comfort and custom adjustment. The fabric is supersoft and the set runs true to size. Plus, the length of the pants is great for tall people.

Columbia Women’s Hatana Breathe Hiking Shoes 

Take advantage of temperate fall weather by investing in a good pair of walking shoes. These Hatana Hiking Shoes from Columbia hold their weight against any terrain. The breathable, open-mesh design is great for keeping your feet cool, and the outsole offers incredible traction in both wet and dry conditions. I’ll pack them for my trip to London as I traverse some 1,500 walking and biking trails that inevitably lead me to my favorite restaurants in the city.

Kancystore Button-down Tie-knot Top  

An easy, loose-fitting shirt, like this pick from Kancystore, is a great addition to any fall packing list. The lightweight fabric and deep-V neckline provide a stylish cut and easy movement. Choose from 22 solid colors or polka dot prints, and dress it up or down with jeans, shorts, or a skirt. I’ll be packing it for an afternoon of walking through my favorite Brooklyn neighborhoods. 

Rollas Women’s Sailor Scoop Carla Jeans

Functional, comfy jeans are key during shoulder season and can help any outfit shift from day to night. I love to pair these ankle-length jeans from Rollas with my favorite lace cami, layered with an ultrasoft and light cashmere sweater. The high-waist jeans have two back pockets to store items, and a loose fit through the thigh makes moving around easy. As food festival season in California gears up, I’ll wear these for their supreme comfort to events like the L.A. Times Food Bowl, a weekend-long showcase of the city’s best restaurants.

Vera Bradley Large Duffel 

One of the things I love most about living in California is the easy road trips and quick flights I can take to the Pacific Northwest. This large cotton duffel from Vera Bradley is an excellent option for weekend getaways where you don’t want to be bogged down by a wheeled carry-on or larger luggage. My favorite design is the paisley sunflower pattern, and the exterior of the bag includes two side slip pockets. The bag is made from natural cotton fibers and is easily washable.

Qikaka Long Blouse Dress 

I’ve never been a pumpkin spice latte, sweater type of woman, so I love that fall’s shoulder season brings with it balmy summer days from time to time in my home state of California. This blouse dress from Qikaka covers my arms but is still breathable enough as a dress to combat the higher daytime temperatures. Puff sleeves and a belt that cinches the waist gives this dress a sophisticated look. I’ll be packing this dress for a quick road to The Resort at Pelican Hill, an oasis in Newport Beach that offers a number of fall experiences and excursions. 

The Jacket Maker Alison Leather Biker Jacket

It’s that time of year to pull out your favorite leather jacket, and my pick comes from The Jacket Maker, a brand known for its high-quality leather products at accessible prices. This Alison Leather Biker Jacket is the perfect mix of vintage and classic styles, and includes zippered cuffs and a notch-style collar. A quilted polyester lining and removable waist belt are just a few more of the details that come with this biker jacket.

Gonex Compression Packing Cubes  

Shoulder season’s varying temperatures require that packing lists cover all bases. These compression cubes from Gonex are incredible for reducing space in your luggage, especially if you’re an overpacker. Double zippers work to compress clothing items and quick grab handles make pulling the cubes a cinch. Rip-resistant nylon offers great durability against tears, too. I recently returned from a river cruise with Hurtigruten’s Svalbard Line that traveled just miles away from the North Pole. These cubes prevented warm, bulky pieces like sweaters from taking up my entire suitcase. 

Farm Rio Flora Tapestry Red Blouse 

I’ll always find an excuse to wear something from Farm Rio, and this Flora Tapestry blouse is another perfect excuse to find room to pack it for my fall travels. The detailed puff sleeves with floral and crochet trim will stand out in any room. If you’re looking for a more affordable option, this ruffled piece from Luyaa is also available on Amazon for $20.

Melissa Original Jellies 

I’ve always been a fan of the vegan and eco-friendly Melissa shoe brand. These jellies are the nostalgic blast from my past and my favorite fall shoe companion. I like to liven up more standard outfits with the mixed glitter glass color and can’t resist the fisherman-style design that I used to rock as a child. This version gets an upgrade, with a cushioned footbed, arch support, and hypoallergenic, nontoxic, and water-resistant materials that are built to last. 

EACHY Large Travel Makeup Bag

This large cosmetic bag from EACHY easily holds some of my favorite fall skin care products. The flat design and really wide opening make it easy to access products when you’re on the go. It’s also multifunctional and can be used as a toiletry bag or even a purse. The interior pockets are also handy to store smaller items, like my favorite lipstick, and travel-size products. 

AliceLife Acotavie Lightweight Floral Scarf

For cooler nights that don’t necessarily require a heavy jacket, or an outer layer at all, this lightweight floral scarf is a great choice when you want to keep your body warm and remain stylish while doing so. This floral print evokes some of my favorite fall foliage moments, and since it’s not bulky, it’s also very easy to pack. 

Voilipex Floppy Straw Sun Hat 

I’m a huge believer in sun protection year-round, even when temperatures begin to dip. This floppy straw sun hat from Voilipex is made from 100-percent natural paper straw that’s lightweight and breathable. The hat can be folded into your bag without losing its shape and the wide brim can protect you from the sun’s harmful rays. I’ll be packing it for an overnight stay on the glittering Pacific Coast after checking in at The Ritz-Carlton Laguna Niguel, known for its prime stretch of beach and Taikun, an exclusive nine-seat pop-up omakase residency from acclaimed executive chef Kei Yoshino. 

Naturopathica Manuka Honey Moisturizer 

Just like the temperatures during fall, my skin’s hydration can also change with the seasons. I’ll be packing this manuka honey whipped oil from Naturopathica on my upcoming trip to Vancouver. It aids in sealing in moisture and protects the skin from pollutants with ingredients that include jojoba oil and manuka honey, which acts as a humectant. 

Sundae Whipped Shower Foam 

Dry skin inevitably shows its face during this time of year, and soaps can oftentimes dry it out even more. When that happens, I rely on this whipped shower foam from Sundae to moisturize my skin. The lemon-zest scent is refreshing and ultra-hydrating. I also love that it’s vegan and cruelty-free, with no parabens. 

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