Work (Road) Trip Style: 3 Comfortable Outfits for Work Travel by Car or Airplane
For four straight weeks from the end of July to beginning of August, I traveled for work all around the state. Each trip lasted between 1 and 3 days, so it wasn’t like I was gone for a solid month (whew!), but it definitely felt like I had been by the time I got home from the last trip! Last week was the first week I didn’t travel and it felt like the longest week ever, haha. I ended up with two full days of comp time by the time it was all said and done!
I’m actually surprised that it happened, because last year, it sounded like work travel would not be approved for at LEAST two years due to the pandemic. Surprise! I got to travel (along with a few of my colleagues). Three of the trips involved only driving time (1.5, 3-4, and 5-6 hour drives) and one involved a short flight and short drive. (It was my first time flying in nearly two years!)
Typically when I travel for pleasure, I wear leggings or joggers and sweatshirts. Basically, I try to dress as comfortably as possible, and I don’t care that much about how I look. For work travel, my goal is to dress the same way…but the challenge is dressing in work-appropriate clothes that are also comfortable enough to travel in. I knew I’d be sitting in these outfits for hours at a time, so I wanted to put together outfits that could be worn in the office yet were easy to sit and move around in. (To be quite honest, these outfits are no different than the ones I wear to the office on typical work day where I’m sitting for 8 hours. Ha!)
I always caveat my workwear posts with the fact that my office is on the casual side of business casual, so I wouldn’t feel out of place wearing any of these outfits to my office, even when it’s not Friday. I actually feel really dressed up when I wear a blazer instead of a cardigan these days! If you’re in an office that isn’t as lax about jeans and tees, I’d probably pull out my trusty pair of ponte pants or another pair of stretchy non-denim pants for travel. Stretchy midi skirts would work, too!
All three outfits feature the same basic uniform: tee + jeans or pants + sandals + third piece (blazer or cardigan). Not getting too complicated with the silhouette kept packing and outfit building easy. Here are three comfortable outfits I wore for recent work travel!
3 Comfortable Work Outfits for a Road Trip or Flight
I brought this J.Crew Sophie sweater blazer on all four work trips. I have two other colors, but I just love the bright and earthy heather fern! It’s a beauty, and I love that it adds interest to a regular white tee and grey skinny jeans outfit. My Madewell Roadtripper jeans are one of my two most comfortable pairs of jeans, so of course they came on all my trips as well. I’m obsessed with these and wear them at least once (usually twice or more) a week during a normal workweek.
Slip-on sandals made most of my trips as well; they’re comfortable and nice-looking! (Note that I didn’t do any driving on any of the trips; I would have changed into sturdier shoes for that.)
OUTFIT DETAILS
J.Crew blazer / exact (last seen here)
Everlane tee / exact style in organic cotton (review here)
Madewell jeans / exact (also available in tall and a mid-rise style)
Everlane sandals / old; new version or similar by Nordstrom
Dior Lip Glow in rosewood / exact
For my longest work trip (3 days), I brought along a pair of cotton-linen pants. These lightweight pants are perfect for the hot summer months—as is the linen tee! The pants feature an elastic waistband but still look nice enough for the office, though I don’t think pants like this look quite as nice in a lighter color. Darker colors look more polished/hide wrinkles more easily.
Even though it was the middle of summer when I traveled, I brought along my camel cashmere cardigan on nearly every trip to serve as a warm layer in the chilly office buildings, for when my colleagues preferred to have the car A/C on full blast, and while flying. I always seem to run cold!
I wore basically this exact outfit when I traveled for a work conference two years ago! It never gets old. 😉
OUTFIT DETAILS
Grana cardigan c/o / old; similar by Banana Republic (last seen here)
Everlane tee / old; similar by Madewell
J.Crew Factory pants / old; similar by H&M or Macy's
Salt Water sandals / exact from Zappos
Dior Lip Glow in rosewood / exact
I had to present during my last work trip, so I brought along the big guns: a ponte knit blazer. Groundbreaking, I know! Haha. I actually would have no issue wearing my sweater blazer but decided to mix it up for this momentous occasion. Like I said above, putting on a blazer makes me feel instantly more formal, even if I am wearing jeans and a tee underneath. I can no longer deal with stiff wool blazers so I’m all about my collection of stretchy sweater and ponte knit blazers!
I ordered the Madewell curvy skinny crop jeans in Lander wash last month and immediately added them to the rotation. They are currently my number 1 most comfortable pair of jeans (just barely edging out the Roadtrippers), but that is because they run just a touch big. My usual size 25 didn’t have as much give in the waist, so I kept the size 26, but they’ve actually stretched out enough that I think the 25 would have been fine. These work really well on my bloated days...or for work travel!
I ended up packing my two Amour Vert modal blend tees on at least one trip each, and when I pulled each tee out of my backpack, they looked hella wrinkly, even after rolling them carefully. I figured out that laying them out on the bed and gently stretching out the wrinkles, then letting it stay like that overnight worked WONDERS. It was like the wrinkles never happened! (Plus, no iron needed!)
OUTFIT DETAILS
Olivia Moon blazer / old; similar by J.Crew Factory
Amour Vert tee / exact style or similar by Old Navy (last seen here)
Madewell jeans / exact (also available in petite and tall) (curvy jeans review here)
Everlane sandals / exact style
Dior Lip Glow in rosewood / exact