Three Day Work Trip Wardrobe (Winter)
When I was planning for a recent work trip, I noticed that I was navigating several tensions I had not felt before. I was planning, executing, and leading the entire retreat for my team — my first time in a leadership role — and I wanted to look professional.
At the same time, I am not a manager. I share the same workload as everyone else on the team, and I didn’t want to dress in a way that signaled I was drifting towards “boss”. I was also meeting my own manager in person for the first time and holding a meeting with top leadership (the guys in suits).
And of course, the outfits had to work for real life: airport to office to dinner. So the brief became: professional-leaning business casual — not too fancy, not too casual, and comfortable enough to instill confidence.
I have worked from home for six years. Back when I went into an office every day, I had my own very comfortable version of a uniform: blazer, dress shirt, dressy chinos or slacks, dress shoes or boots. Every now and then I would add a tie if I was feeling particularly cheeky.
But the business world is much more casual now — even in a big law firm. More importantly, I’ve outgrown most of my old work wardrobe in the literal sense. So for this trip, I needed to adapt what I used to know about office attire into something current, comfortable, and appropriate. The new version is softer and a bit more casual.
Day One — airport to office to casual informal dinner
I aim for casual but clean with a few items that do some heavy lifting. Loafers make it easier to get through security at the airport. A thin v-neck sweater keeps me warm on the flight. When I get to the too-warm office, I can roll the sleeves. By late afternoon, the sweater ends up folded over the back of my chair — a small reminder that travel days always begin colder than they end.
For drinks and tacos with my work pals, I ditch the sweater and roll my shirt sleeves to the elbows. The best part is the cozy sweats, t-shirt, and slippers waiting for me when I get to the hotel room after a long day.
Day Two - office marathon to retirement cocktail hour to upscale dinner
I take the old office uniform feel and upgrade it. The blazer is replaced by a cardigan — same vibe but less structured. More approachable. A soft pink shirt is calming and the color makes my face light up. Burgundy socks provide a colorful anchor without the comedy of novelty socks. Same loafers.
My briefcase is filled with little items that add stability or comfort throughout the day. The travel fan comes in handy between meetings when I’m rushing to get as much normal work done as possible and start overheating. A tiny pause to let the artificial breeze cool my face. Then a glance at my watch — time to finish the workday strong.
Day Three - big team meeting to training to airport
I want to capture a little of the casual Friday feel that I used to look forward to. Slim corduroys in dark forest green are the star of the show. I choose a more casual cotton sweater, but immediately have to ditch it in the still stifling office. (Note to self — put the lint roller in the briefcase next time.) Low-profile suede shoes with a moc toe and lug sole are the perfect choice for that Friday office vibe. (Additional note to self — these are not comfortable enough to wear for a full day of standing when the airport runs out of seats during winter travel chaos.)
Speaking of the airport — a few well-timed treats can feel like a major mood boost. A ball cap stashed in the briefcase becomes an internal signal to “let my hair down” after I leave my coworkers at the food court. I pair it with the noise-cancelling technology — and “please don’t bother me” energy — of the headphones and the latest issue of a favorite magazine to create my own little world in a corner while I wait for my flight. Oh, and that sweater came in handy once I got settled into my seat. First class is cool.
In the end, the goal wasn’t to dress like a boss or an employee. It was simply to feel steady enough to do the work.
