Best Road Trip Outfits to Travel In This Year

Road Trip Time! This post is about the best road trip outfits to travel in this year. It’s been over a year since we’ve taken any kind of trip, and I am longing to get out and travel again.  After considerable discussion, we’ve booked two road trips this season, one of which is a short trip with sight seeing and a stay in a bed and breakfast for a few days.  The plan is to get our feet wet by taking a short easy trip before tackling a longer multi-day on the road trip to visit family.  

Trip number one entails just a few hours in the car, a family gathering on the beach, a few days of site seeing, then home.  The second trip will entail several days of driving, several days visiting family, then several days to get back home.  We even talked about making a big loop while we are out and visiting even more family—might as well, right?  All a girl needs is a pile of cute travel outfits.

So let’s get to the important stuff, putting together stylish travel clothes.  Whether you are going on a weekend getaway, or a longer trip, this is your one stop spot for travel outfits.  I love answering your questions because I ask the exact same ones  myself, and have been thinking of what to wear on these road trips ever since we started talking about them a few months ago—one will be a summer trip and the other will be in the fall.   Naturally, I want a cute road trip outfit—or actually a road trip wardrobe.  My list calls for versatile pieces that will be comfortable for the long drives. The look I’m going for is casual chic or cozy chic when we hit the open road.

Before you begin packing:

I like to check the weather as I begin my packing process, and list the activities we are planning.  I also throw in a swimsuit and workout clothes so I have a few options in case we have some down time.  Having your trip mapped out a bit on paper helps ensure you don’t end up with the wrong clothes and helps to make sure you pack a rain coat or snow clothes— or have light weight clothing in case it’s warmer than you thought.  You might consider putting together a few travel kits—one with cords, another with hand sanitizer and wipes—for gas station stops and minor emergencies—like spills and such.

Planning your road trip outfits:

1. Build your outfits around your shoes:  this works great because often shoes take up a lot of room and weight in our suitcases.  If you build your outfits around your shoes, and create outfits around two or three pair of shoes, this will really help reduce extra items in your suit case.
2. Plan each outfit in advance and take a photo of it:  I love doing this because I always seem to forget which accessories go with an outfit or some of the mix and match ideas I had when packing.
3. Look for comfortable pieces that can be worn in different combinations-this is key to avoid over packing.
4. Remember, we often end up wearing the same things over when traveling—don’t try to take it all—keep with a mix and match theme.
5. Don’t forget your undergarments, socks, bras, and panties.
6. Look for items that are easily laundered if you are going to be on the road for a long time.
7. Check the weather to ensure you don’t need rain gear or other special items for weather issues.
8. Think cozy chic or casual chic when planning the outfits you will wear in the car.
9. Don’t forget accessories to elevate your travel wear.  Honoring your personal style will help you feel more at ease when traveling.
10. Think about wearing your outfits in different ways to extend your outfits, perhaps by adding a little color, a favorite top, or graphic-t.  

What should you wear on a long car ride?

1. Tank tops, camisoles, and t-shirts:  Whether  the weather is warm or cool, I always pack these essentials.  They work great for layering, are easy to wash and wear, and can be used for sleeping, and using the gym—so you don’t have to bring workout wear, if you don’t want to. I always have a tank top and underwear in my carryon bags when we fly-you never know when you might need a change of clothing or something to sleep in.  When ever possible, I go for natural fibers in my wardrobe.  They keep you cooler in the summer and warmer in the winter.  Aside form linen and silk, they are easy care as well.
2. Denim jacket, cardigan or blazer:  Add something to throw over your shoulders on a cool evening, or  a “third piece” to create a chic look.  Denim jackets are super versatile-but if you aren’t feeling the denim jacket vibe, elevate your look with a blazer or choose a big cozy cardigan.  I always take a light jacket or sweater in the summer because air conditioning can be so cold, and these versatile pieces are great options in the cooler months—we always need those layers.
3. Leggings yoga pants and joggers:  I swear by my black leggings, wide leg yoga pants and comfy joggers on road trips.  Because I’m not super laid back casual, I will add an oversized blazer or cardigan over leggings and a long duster over joggers to elongate and slim the look.  
4. Oversized Button Down:  I love an oversized button in natural fibers such as linen or light weight cotton for summer, and something a bit thicker for winter.  Having a shirt with long sleeves is great over a bathing suit, or under a sweater in the winter. Some companies sell women’s travel shirts made of fabric which is easy to wash and wear—so if you are planning a long trip, or you travel a lot, you might want to check out travel specific clothing which is made to resist creasing, and is easy to wash and layer.
5. Midi or Maxi Dress: During the summer months I love to wear dresses, and they can be a comfortable and chic travel option allowing you to look put together while traveling or site seeing.  Packing your favorite summer dress to have on hand for dinners and unexpected occasions is always a good idea.
6. Comfortable shoes:  Some swear by flip flops—but I am not one—for travel, I like to have a comfortable pair of shoes and a pair or sandals for summer and a pair of trainers or booties and a pair of dress shoes for winter.  The reason I don’t like flip flops is because you never know what type of situation you might find yourself in on the road, so having a pair of regular shoes is a safe bet. Some like ballet flats or loafers for travel; these are a matter of personal style and taste.  
7. Skinny Jeans and Travel Pants: When considering whether to bring jeans, cargo pants, or travel pants, make sure they are comfortable and flattering.  Sometimes skinny jeans can be a bit binding and uncomfortable when you ride or are seated for a long time.  A pair of denim jeans might be great to take on the trip, but for the car ride you might feel more comfortable in something with a little stretch.
8. Packing for the seasons:  In summer, don’t forget a a bathing suit, sunscreen, and bug spray.  For winter, remember to pack a winter coat and boots.  

How to look good when you arrive at your destination

It can be challenging to look good after long drives.  Touch up your makeup and comb through your hair just before arrival. Wear a nice outfit so when you step out of the car you will look pulled together.  Avoid fabrics that rumple and crease. Look for clothes that have that casual chic vibe and are comfortable when sitting long hours in the car.  If you like to ride in the car without shoes on, slip them on so you don’t have to look for them when you arrive.

Take a rest break just before arrival to  gather yourself, tidy the car and be sure you look presentable. This way, we can get out of the car and greet family members or go into a hotel we look good.  

It makes it easier for the valet if the car is tidy, and it is a courteous gesture not to hold everyone up while you fumble around looking for your belongings when you arrive.

If you are jumping into action when you arrive, be sure to dress in adventure ready clothes—for what ever activity you have planned.  Again, it’s always a good idea, unless you simply don’t have time, to be prepared and ready to go, no matter what adventure awaits you.

What not to wear on a road trip

1. Avoid fussy clothing that creases easily,
2. Avoid  flip-flops—wear shoes instead to protect your feet.
3. Avoid shoes that are difficult to take off, especially when flying.
4. Avoid over-packing—we often end up wearing the same comfortable outfits over and over while traveling.  When unpacking after a trip take note of what you wore and didn’t wear so you won’t take items you know you won’t wear.
5. Avoid traveling in pajamas.  There was a time when people dressed in their best clothes.  These days, it’s not uncommon to see people wearing their pajamas in public.  Try to put together “every day wear” rather than what you wear in your bedroom.  The objective is to look stylish in your travel clothes.
6. Avoid wearing workout clothing to travel.  Blend workout pieces like leggings with a graphic-t and perhaps a Moto jacket so that you don’t look like you just came from the gym.

Accessories can often add comfort and an extra element of style to your travel outfits.

1. Sun glasses are great for sunny days-obv-but can also be worn on a “no makeup” day.  Just add a bold lip and you are good to go.
2. A cross body bag or a tote bag (I often take both and pack my handbag inside the tote bag.  Having a small clutch that can hold your cell phone, room key and money is also really good when you are pool side or just going to the lobby for a drink.  
3. Lip balm is great for dry air and cold climates. Nothing worse that cracked dry lips!
4. Extra hair ties are always handy-and who knows-you might  use one MacGuiver your self out of a tight situation!
5. Hand sanitizer (and face masks) wipes and a first aid kit are always good to have on hand. 
6. Consider the size and shape of your luggage—a duffle bag is perfect for weekend getaways, while a roller suit case is best for longer trips.  I also like to use a carry on bag for weekend getaways, they are a perfect size for short trips.

As I write this, I am thinking about my best travel clothes—most of which are a part of my everyday wear.  At the end of the day, we want to look and feel amazing when we travel-right? I hope this post has helped you put together cute outfits perfect for your next road trip.  Whether you are heading to a warm or cool climate.  I hope you’ll look chic when you reach your destination.