✨Free Pickup✨ Santa Rosa/Healdsburg/St. Helena

Vacation Outfit Ideas for Your Fall/Winter Trip

Posted on August 11 2018

Vacation Outfit Ideas For Your Next Trip | Travel Fashion

Summer may have passed us by, but that doesn’t mean those of us with serious wanderlust in our blood aren’t already planning our next trip. Vacations aren’t just for summer break! Depending on where you want to go, you can scoop up some excellent off-season deals and see corners of the world that you’d never consider during peak season. When you’re traveling in fall and winter, you need to plan accordingly so that you can cover all your contingencies without overpacking. Thankfully, we’ve got plenty of vacation outfit advice.

Before we jump right in to vacation outfits, let’s start with the basics. Like, you know, where you should go. Fall and winter are unique travel times and you can hit a lot of destinations during these months. But where to?

Here are our top picks for best spots for a fall/winter vacation:

American Northeast – You can’t beat seeing the leaves turn color in the Northeastern states. There’s nowhere better to get that fall feeling.

Utah or Colorado – We have primo skiing in California, of course, but there’s something magical about the mountains in Colorado and Utah. Try Aspen!

Italy – Rome is basically uninhabitable in the summer, but in fall and winter? Gorgeous. Take that Italian getaway!

Switzerland – If you can think of a more iconic and beautiful place to spend a cozy winter, we’d like to know. This country has charm for absolute days.

Now that we’ve established the “where,” let’s talk about what to wear. First things first: are you headed somewhere warm or somewhere cool? A lot of your vacation outfit will depend on your destination.

Vacation Outfit Ideas for Cold

BB Dakota Tucker Coat in Tan

1. Layers, layers, layers. So many layers. Pick clothing you can get more than a single wear from if you want your bag to weigh less than a ton. Choose underclothes, light sweaters, versatile shirts, cozy cardigans, and a favorite jacket or two.

2. Invest in thermals. Thermal wear is super toasty warm and lightweight, making it both easy to pack and easy to wear under your outfits. It’s not something anyone else will see, but it’ll keep you plenty warm so you can wear what you like over it.

3. Accessories that are cute AND functional. At bare minimum, you’re going to want to have a hat, a scarf, some gloves or mittens, and warm tights. There’s no reason why those things can’t be cute as heck! Make sure to go with neutrals so you can match them with as many vacation outfits as possible.

4. Pick base colors and work around them. Choice are fun, but if you want to keep your packing light, stick to one “base” color (usually the color of your pants/skirts) and built the rest of your travel fashion wardrobe around that. Most people go with black, denim, or khaki. Keep in mind that black absorbs heat more than light colors, which reflect heat! Choose multi-functional and fashionable shoes. It’s so tempting to fill your suitcase with shoes for every occasion, but when you’re dealing with snow and cold, you really want to stick with two or maybe three pairs of boots that look great while still protecting you against the chill. Soles that don’t slip on ice are beneficial, too.

5. Mix and match to keep packing minimal. It is SO easy to overpack when you’re going somewhere cold. Rather than throwing in every sweater and pair of jeans you own, go with a minimalist packing method that allows for maximum outfits with less baggage. Tops are going to be the bulk of your packing, but from there, go with one warm skirt, two pairs of jeans or warm pants, one sweater, one good jacket, and 2-3 pairs of shoes. Don’t forget warm socks! Focus on accessories to dress your look up. Sunglasses. Obvious, maybe, but put it on your packing checklist anyway. Glare can be a killer.

All right, we’ve decided where we’re going and we know how to pack around the weather. But what about fashion, you ask? We know how to pack well, but can you do that and still have a sense of travel fashion that makes you the envy of the resort or chalet? Of course you can! Here’s our vacation outfit advice for balancing a reasonable amount of baggage while maintaining your sense of style.

Choose Statement Pieces


We talked a lot about neutrals and packing pieces you can mix and match above, but that doesn’t mean you have to be boring. Statement pieces, like jewelry, belts, and scarves, take up far less space in your bag and can still take an outfit to the next level. Depending on your style, you can go with metals, prints, or brilliant pops of color.

Save Room for a Stunner

If you pack wisely, you can manage to carve out enough space in your suitcase for fabulous one dress or faux fur jacket that really stands out. Consider this your “fun” outfit and pick something you truly love and feel amazing in. It can be a beautiful cocktail dress for a fancy dinner. Put your full fashion on display!

Dress for the Trip You’re Taking

Everyone travels differently. Some people love spending tons of time hiking, skiing, and being outdoorsy. Others prefer relaxing days followed by clubbing at night. Whether you’re more of the night-on-the-town type or the sightseeing at historic landmarks type, your vacation fashion choices should coincide with your activities. Whether that means mini dresses or snow pants is up to you!

These are some of our best tried-and-true travel outfit ideas. Our absolute favorite look for cooler weather is a simple pair of dark jeans, ankle boots, and a cream sweater. Simple, classic, and easy to mix and match. When you’re rocking travel fashion like this, you’re sure to turn heads.

Come see us at PUNCH Clothing to pick up all the essentials. Our sales associates would love to hear about your trip! What’s your favorite vacation outfit advice? Let us know how you keep your sense of style when you’re on the go.

More Posts


Leave a comment