Layer Up: Packing for the Transition Season

The transition season can be a packing nightmare. The only way to go is to layer up.


As we move from summer to fall, we start to see cooler mornings and evenings. But the afternoons are often still sunny and warm. And if you’re on a road trip or cruise where you start in one place and finish in another, you may experience many climate shifts throughout your vacation. For example, on an autumn cruise up the east coast from NYC to the Canadian Maritimes, temperatures can range from 50 to 85 degrees, depending on the location and time of day. What’s a girl to do? If you’re looking for exciting things to do and places to explore during the transition season, click here to see an example East Coast driving itinerary.

You don’t want to lug around a lot of heavy cold-weather gear, but you do need to stay warm. Here are some stylish ways to layer up for your transition season travels.

layer up

Kimonos and Capes

Even in warmer places, there’s a nip in the air in the very early or late hours of an autumn day. Pack a lightweight kimono or cape sweater in a neutral color to keep out the chill. Paired with skinny jeans or leggings and a super-soft tee, you’ll look great and feel good. Not to mention, you won’t have to worry about lugging around a heavy jacket when the weather warms up later in the day. Kimonos and capes fold up pretty small and should fit nicely in your purse.

Layer Up Kimono


These days, sweatshirts are about as stylish as they come. Whether you prefer something casual with a punny slogan or one with some embellishments, there’s something for every taste. From lace to beads to embroidery, there are so many styles to choose from. Throw one of these on over top of a chambray shirt, white button down blouse, or plaid shirt, and you’ll look adorable in your layers. When the sun comes out, simply tie your sweatshirt around your waist, and you’re ready to go.

Layer Up Sweatshirt


Vests add a bit of pizzazz to any outfit. They look amazing with skinnies and ankle boots, and don’t even get me started on how they look popped over a cute little jersey dress. For the perfect neutral, toss a military-style, olive-green vest into your suitcase. That color and cut will go with just about anything you can think of.

If you’re planning of a lot of morning or evening walks, a puffy, down vest will do the trick. The best thing about a vest is that it’s not bulky. Your arms aren’t bogged down by the weight of a full jacket, so you can take pictures more easily and shop for souvenirs without the fear of knocking knickknacks of the shelves with your bulky sleeves.

Layer Up Vest


Sometimes, you simply can’t avoid taking along a jacket. The east coast cruise vacation is a perfect example. Some days will simply be too cold not to have something with a little extra heft to keep warm. Luckily, there are a lot of options. A denim jacket is a classic that goes with everything. These days, you can even wear it with your favorite pair of jeans.

A black or brown moto jacket is also a good option, especially if you’ll be going for a night on the town. It’s a bit edgier and can be dressed up in a way a jean jacket can’t be. Like the vest, a lightweight, military-style, olive-green jacket is a nice neutral. It will likely have a bit more length than the other jackets, giving you a some added warmth.

A personal favorite is a down jacket that folds into a travel pouch. They are ultra lightweight and fit nicely inside your purse. I used one of these on a spring vacation in Spain, and it was the perfect antidote to transition-season climate changes.

Layer Up Jackets

These are just a few of the ways you can layer up during the transition season. Use the #wanderlustwayfarer on Instagram to share your wardrobe ideas.

Transition Season Travel Shoes

It’s hard not to pack 10 pairs of shoes during transition season.


With a cool chill in the autumn air, it’s tempting to pack everything from flip-flops to winter boots. Finding the balance can be a bit of a nightmare. Pack one of each of these four types of footwear, and you’ll have your bases covered for a transition season trip.

Transition Season Travel Shoes


After Labor Day, it’s time to put away bright whites and summery styles. It’s okay to still wear sandals, but make sure they’re autumn appropriate. Keep it simple with dark or warm neutrals. And make sure you’ve got a little more coverage. Strappy, tan, gladiator sandals might work well when the sun is high in the sky, but they’ll seem out-of-place in the early morning when the temperatures are low.

Transition Season TRavel Shoes Sandals

Walking Shoes

Depending on your plans, a good pair of walking shoes will mean different things to different people. For typical tourist activities, like hop on hop off buses or shopping, a pair of canvas sneakers should do the trick. Think Converse or Toms. If you’ll be on your feet for hours at a time, you may want to consider something with a little extra support. Skechers Go walks will make you feel like you’re walking on clouds. If you’re thinking of climbing mountains or chasing waterfalls, a good pair of hikers is in order.

Transition Season TRavel Shoes Walking

Pro Tip: If you’re going someplace where it’s expected to get a little wet, you may want to swap out your sandals for something a little more practical, like a pair of wellies or duck boots.


You can’t go wrong with a good pair of flats. They don’t take up much room in your bag, and you can wear them a lot of different ways. For a casual shopping day, they’re a great way to dress up jeans and a tee. And they look great with shorts or even a cocktail dress. If you’re not into black, try a jewel tone for fall. Dark green, for example, is a great alternative to a neutral color. For a flirty look, choose a flat that has a little glitter or a funky pattern. Yosi Samra makes an amazing array of flats that fold up so you can take them with you wherever you go.

Transition Season TRavel Shoes Flats

Fancy Feet

To cover all of your bases, pack one pair of dressy shoes. As with the sandals, for the transition season, darker or neutral colors with more coverage work best. But it’s okay to have a little fun still. A pair of black, lace-up, block heels or a burgundy peep-toe ankle boot will spruce up any fall outfit. And, of course, you’re always safe sticking with a traditional pointy-toe black or champagne pump.

Transition Season TRavel Shoes Fancy

Pro Tip: Wear your biggest pair of shoes on the plane to save space in your bag. This may be your hiking books or a pair of heels. Cheat a bit, and toss a pair of $2 flip-flops in your purse as your fifth pair of shoes. You can slide them on for comfort once you’re seated on the plane. (And they can double as your pool shoes later in the trip.)

These four styles of footwear will keep you looking good through the transition season. Tag your travel shoe pictures on Instagram with #wanderlustwayfarer to share your ideas.