I’ve Been on 16 Trips This Year—Here Are the 7 Comfy Basics in My Travel Wardrobe

Now that it’s fall, there are a few orders of business: planning your next vacation (I’m on my 20th, oops!), ordering anything pumpkin spice, playing Red on loop, and upgrading your closet with some trendy fall pieces. But, I’m heading to Spain soon and totally failed to realize the weather is now chilly there as well, meaning I need to bring fall clothes—RIP to my linen and crochet set vision.

But if you’re anything like me, everything you wore last fall no longer speaks to you and thus, can’t be brought along on your travels, so now you’re itching to do some shopping. But instead of getting an entirely new wardrobe—which, unfortunately, is very expensive—you can add a few pieces to mix up what you already own, like a trendy pair of black satin pants, a barn jacket, or a new pair of boots, all of which are also comfy and airplane-friendly, too.

7 Travel-Friendly Fall Staples 

There’s nothing worse than spending a lot on items you’re realistically never going to wear more than once, and as someone who shops for a living, I’ve made that mistake far too many times, especially when vacation shopping. Not only is it a waste of money and bad for the environment, but who has the closet space? Below, shop the pieces I’m buying for my upcoming trip that I know I’ll wear year after year—maybe I’ll even pass on to my hypothetical children (I don’t even have a boyfriend!). 

TL;DR? These items aren’t too trendy or over-the-top; they’re just chic and timeless and they travel well, a.k.a., they’re easy to pack and even easier to wear while you bop around from city to city.

Madewell Pintucked Slim Pull-On Pants

These satin pants can be worn year-round and pair nicely with anything. A cute striped sweater? Yes. An oversized blazer and a corset? Absolutely. A matching satin top? Yes, yet again. Available in petite, standard, and tall sizes, they’re designed to fit any body type and come in five shades, including true black and sun-faded indigo.

Rag & Bone Miramar High-Rise Wide-Leg Cotton Terry Sweatpant Jeans

When in doubt, do as Jennifer Aniston does—she’s been spotted in these sweatpant jeans many times over the past few years. Recently, I decided I want to be the kind of person who travels in jeans, but I can only opt for super comfortable ones like these. No one will be the wiser that there’s an elastic waistband up top.

Everlane the Barn Jacket

According to my Instagram feed, big farming won this round—barn jackets are back in style. This one from Everlane has a slouchy, relaxed fit and comes in three neutral shades: black, cornstarch, and beech. Made from organic cotton canvas, it drapes nicely and is available in sizes XXS to XXL. If that wasn’t enough, Martha Stewart has also been spotted in the style—coastal fall look, anyone?

J Crew Cropped Fringe-Trim Lady Jacket

An easy way to upgrade your wardrobe or start dressing more maturely is by adding a lady jacket. This style from J.Crew is sophisticated yet maintains a youthful playfulness with its cropped silhouette, swingy fringe hem, and short sleeves. It comes in three shades (I want them all!) and sizes XXXS to XXXL, though the brand suggests sizing up for a more relaxed fit.

Anthropologie Silent D Cabana Boots

A good pair of boots will elevate any outfit, especially if you’re feeling uninspired by your current wardrobe. These boots from Anthropologie are super comfortable, even with the 2.75-inch heel, so you can walk miles on end without dealing with annoying blisters. They come in three neutral shades as well as a trendy cheetah shade. A fair warning that they’re made of pleather, though.

Birkenstock Boston Clogs

I still regret not buying these Birkenstock Clogs last year, but there’s no point in living life with regrets, so I’m scooping them up this season. They’re an excellent purchase because you can wear them year-round, either outside or as indoor shoes. I love my Birkenstocks, but in winter, it can be too chilly for sandals, and I really dislike the idea of exposed toes in the city. 

Banana Republic Factory Timeless Trench Coat

A trench coat is the easiest way to go from frumpy to chic without expending too much energy. This one hits just at the knees, and when buttoned or tied with the included belt, no one will even know you’re wearing pajamas underneath. It’s light enough for those in-between weather days but can be paired with a sweater or thermals when it gets really cold. Plus, it’s made from a water-resistant fabric, so you can wear it rain or shine without worry. The best part? It’s currently on major sale.