What to Wear When You’re Out of Town & Working Late
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What should you wear when you're out of town and working late? Reader H is gearing up for trial and wonders what to wear in the war room after hours:
I am going to be attending a two week out of town trial with two partners at my firm. During the day we will all be in suits, but in the evenings we will likely be working late. I will want to be in comfortable clothes, which for me would constitute yoga pants, but do not think that would be appropriate with my boss. Any suggestions?
Interesting question! We've talked about what to wear on the weekends, what to wear for a month in court, and traveling for work, but not this question.
My Tips on What to Wear When You're Out of Town and Working Late
I was in exactly this situation a few years ago — and I'm not sure I made the right decisions. In my case, we had set up a war room at our local co-counsel's office, which was walking distance to our hotel. Each night, after the close of trial, we would return to the war room and start our real work for the day.
{related: what to wear to be super comfortable at work}
(This was a very small team from my firm — just one (male) partner, myself, another (male) associate my level, and a paralegal. We also worked with two lawyers from our local co-counsel's office, a temp secretary or two, and occasional visits from our client's general counsel.)
This is what the guys wore after hours: suits (my associate) and (for the elderlyish partner) what I always thought of as “boating clothes” — scruffy college sweatshirts and ancient, tattered khakis, worn sockless with Keds (if memory serves!).
I don't totally remember exactly what I wore after hours, but I remember thinking that I made a huge mistake in my shoe choices: I had two pairs of heels for my suits, a pair of running shoes (in the hopes that I'd get to the gym — instead, I got walloped with a bad cold the day before trial started and I spent the rest of trial worrying I was going to get my elderly partner seriously sick), and — wait for it — a pair of Uggs.
I'm not even a huge fan of Uggs for comfort, but I figured they were black, would blend with my outfits more than my Chucks, and that they could also serve as slippers around my hotel room or if there was some middle-of-the-night fire drill. I think the Uggs would have been fine for the war room, honestly, but I'm ashamed to admit that I wore them to drinks/dinner with the GC and partner at least once, if only because I had neglected to pack “professional but not a suit” clothes.
TL;DR: Nice(ish) Weekend Wear is Fine for When You're Working Late
So: Looking back: I think weekend wear is fine for most late nights and, you know, weekends. If that's (non ripped) jeans, fine — if it's workout pants (provided that they are a) opaque, b) not tight enough to see underwear lines, and c) aren't too crazy on the color spectrum), that's probably fine as well.
Comfortable but Polished Clothes for When You're Working Late
All that said, if you do want to go for a bit more polish when you're working late — or if you're frequently in this position — then I would highly recommend getting more comfortable office clothes, whether they're pull-on pants for work,
There are a bunch of great pull-on pants for the office in 2025. Some of our longstanding favorites include those from Athleta*, Eileen Fisher*, Betabrand*, and Uniqlo. If you're looking for something a bit more polished but still ultra comfy, check out Nic & Zoe* or NYDJ*. (Brands with plus sizes are marked with asterisks.)
But don't forget to pack at least one “going to dinner but not wearing a suit” outfit, as well. Think a simple pair of trousers, a light sweater, and a pair of heels or flats that you won't have already worn all day (if only for comfort).
A sweater jacket is a great way to add some polish but in a friendly way — add to a sheath dress or even with jeans.
Some of our favorite sweater jackets for the office as of 2025 include M.M.LaFleur (the OG, the jardigan!), L'Agence, Summersalt, J.Crew, Modern Citizen, and Jenni Kayne. For budget options check J.Crew Factory and Quince.
Readers, what would you wear for after-hours working clothes while on a business trip (i.e., your options are limited by your suitcase)? What would you pack — and what would you avoid? What are your best tips on what to wear when you're out of town and working late?
These lightweight, foldable flats might also be a nice addition to your limited luggage:
Some of our favorite foldable flats as of 2025 include Silky Toes, Yosi Samra (at Amazon and Nordstrom), and Amazon seller HEAWISH. If you're looking to splurge, the Tory Burch travel flat also has a split sole.
Stock photo at top via Pexels/Tima Miroshnichenko.
Psst: while you're out of town…
These are some of the Corporette readers' favorite items for business travel…
This going to be my life in June and while I hadn’t thought it completely through yet, I was thinking jeans/casual skirts and dresses – basically what I would wear to work on a casual friday for after hours work – personally, i would probably stay away from anything too casual, including yoga pants/sneakers.
Forgot to add – I’m planning on bringing some comfy flats/loafers for my casual shoe selection. I’ll still look polished (hopefully) but not too dressy
I had a week-long trial about a year ago and I packed yoga pants and comfy shirts for working in my room. I wore jeans with flats and (usually) the tops that I had on under my suit and a cardigan for when we would go out to dinner. If I were the OP, I’d bring jeans and wear those with a casual shirt and cardigan the first night in the war room, and then gauge what everyone else is wearing. If they’re all casual, wear your yoga pants.
When I was in this situation, I wore sweatpants sometimes when hanging around the hotel (mostly with other associates) but when going to dinner or to the office to work (even in the middle of the night) I wore jeans/t-shirts.
For those of you who remember the somewhat controversial discussion on here about the term “babymoon” – I just saw a headline that Gwyneth Paltrow and Chris Martin are on a “breakup moon.” Apparently any vacation tied into a significant life event can be a “moon” ;)
just wear the yoga pants.
I agree. I tried a case out of town for nine weeks when I was an associate, and believe me, when you’re in a tiny hotel room-cum-war room working around the clock, nobody is going to care whether you’re looking polished.
You will want something decent to wear to dinner, but after that just be comfy.
Ditto this. Also if you are allowed to eat in your war room PLEASE FOR THE LOVE throw away your food. We found a weeks-old ceasar salad container inside a binder box once. It was really special.
Is this a situation that calls for pajama jeans? (only kidding…sort of)
A friend has a pair that I didn’t realize were PJ jeans until she told me — they were actually good looking!
Yeah, I’m going to need some pajama jean recommendations.
The “Jag” brand jeans Kat referenced are this–they have elastic tops. Seriously like PJs They don’t hold up all that well over time from my experience, but they are the perfect thing for something like this or long travel. With a top that comes over the waistband, no one will ever realize you’re in pure PJ-like heaven.
A coworker of mine swears by the Bettonas at Athleta. They seem to have held up well.
I’m going to have to recommend my favorite yoga jeans:
http://shop.nordstrom.com/sr?origin=keywordsearch&contextualcategoryid=2375500&keyword=yoga+jeans
I have 3 pairs.
I have some ponte knit pants from NYDJ that feel great. They are as comfortable as pjs but look much more polished. That said, I’ve only had them for 6 weeks and can’t report on how well they hold up over time.
I’m just a phd student reading here because I know I’m going to need to step up my look soon. But I just looked at that yoga jean link and want to say this looks sorta like my Target Denizon jeans. I buy bootcut, in size 14, in a dark wash, to wear while teaching (with a silky-ish blouse/cardigan/ballet slippers). They have held up well. Target has other cuts in this brand that look similarly comfy. But these pants are SO COMFY. I could totally pull them on and off it I wanted to. I have six pairs and wear them almost all the time. They cost around $30. (Obviously, I’m poor.)
What do you do when you are in the thick of being really unhappy at work? Like so overworked and so cranky. I have a constant headache, I try to eat light and healthy but fail – usually because my blood sugar is so low from being overworked and on a med I’m currently on, that I need carbs to keep going. I’ve gained weight. I don’t have time to exercise unless I actually don’t sleep. As much as take care of yoursel is a battle cry of this site, it’s not an option. They say they will get more help but even if they do it’s not immediate. And someone just took credit for a deliverable I prepared (as in I sent for internal review and the person sent to client). And more work keeps coming through. My whole team is busy but I do think I’m busier than the rest even though I got a new assignment. I’m hanging on by a thread but I need this job, at least to get a new one. I don’t know how to get through. Help.
Some tough love here. You are responsible for your own happiness. If you are unhappy at work, do something about it. Assess your approach to work (do you take on too much? Are you in over your head and unqualified for what you do such that you’re stressing out? Are you incapable of saying no? Are you working to “perfect” when it’s acceptable to work to “good”). Figure out if you can change anything to make it work and if the things that are problems will just continue elsewhere if you don’t do something about them. If it’s just your current workplace, quit. Get another job. Do something else. But stop waking up every day feeling unhappy and like the situation is out of your control because it isn’t. You are in control of your own life.
I will second anon’s advice in a gentler way. Start saying no. Just–no. No I don’t have bandwidth. No, I cannot jump in on X project, No I can’t do an all-nighter tonight. There’s a wide spectrum between having to look for a new job and trying to re-set boundaries at the one you have.
Also, when I’ve been this busy at work, it really helps to come in only 15 minutes early and think about what there is on my plate that I can delegate. Even if it’s really small–copies, mailing a letter…whatever. Trying to bring in extra hands (even if they don’t do exactly what you do) is what you should be thinking of doing. If you are at a small firm/company, resources might be absolutely stretched to the limit, but don’t think that because no one is obviously available that there’s no one. Talk with a manager or whatnot and try to figure out what you need.
Also, automate your life–send out your laundry, order a bunch of healthy snacks from Amazon / stock up on healthy stuff for your fridge at work, like yogurt…make your life really efficient so that all you need to do is fall into bed when you get home at whatever hour.
Good luck–I have been there, and it’s really rough. But it can’t go on forever. You can do it!
Long time lurker (and long time voter for the blog award!) first time jumping in…Aft, I was in the same state very recently. Miserable at work (actually the job, not the work)–as a result of the stress I had ulcers, headaches, sleep issues–the whole 9 yards of what happens when you feel such stress and don’t know how to take a step back.
But take that step back and realize your health and happiness are the most important gifts you can give yourself. Step back from the actual work and figure out on a list what bothers you with where you are and also where would you really like to be? Then you can see next steps.
For me it was changing jobs completely, moving x country with DH for a way better opportunity and taking control of my work life and life life. The stress is minima nowl, we are so much happier. And it started with that pen to paper list of why I was unhappy. That was late last year so it doesn’t take long to start the gears moving for change if you are serious about it. Good luck!
Aft, I don’t have time to address all your questions [see: slammed at aork also :) today] but I really hear you on the carbs and low blood sugar, so these comments address the food. That’s been my problem for years and what’s solved it is easy sources of protein, which will help you avoid the sugar/fat traps. As they say, ya gotta eat.
So pick up some hard-boiled eggs, cheese sticks and nuts for protein. Small foil packets of tuna. Almonds are good, so are cashews and pistachios. Buy bags of baby carrots and a package of hummus. Or pre-sliced apples and peanut butter. Buy these on the weekend and bring in to work. Instead of candy bars, have carrots/hummus or apples/peanut butter. Eat nuts instead of chips. Always start the day with a hardboiled egg or two and some V-8 juice or pre-made smoothie. Get some frozen meals that are reasonably healthy (e.g. Smart ones, Amy’s).
Make sure you fuel with protein as it will help with headaches and energy.
Once an hour, do some simple sitting yoga stretches at your desk. Hang in there.
This is me. Every day, I write down across my notepad “done is better than perfect.” Some days it sinks in.
Seeing as lead counsel in a recent trial of mine held meetings in her pajamas, I think yoga pants are fine.
I disagree completely. Lead trial counsel is muuuuch different than associate in war room. I’d do jeans and comfortable shirts. You can be comfortable while still looking relatively polished.
To be fair, it was a three-person trial team, so “lead counsel” didn’t mean someone particularly high-up or authoritative as compared to the rest of the team.
At the risk of sounding overly prudish, I would never wear yoga pants around my coworkers or supervisors, even in a war room. They’re inherently tight/revealing. Why not dark wash strechy jeans with a soft button-up shirt (maybe even a cozy cardigan) and flats? Save the workout wear for the gym and weekend.
I have a pair of the Champion “premium” pants (not leggings) I bought at Target and they are a nice matte black. They are very thick and not skin tight. I wear them on the weekends as casual wear and they’re not revealing at all. I think these could be made appropriate for weekends at the office or work travel with the right top and shoes, but then again I’m not in law.
http://www.target.com/p/c9-by-champion-women-s-fitted-premium-pant-assorted-colors/-/A-13555970#prodSlot=large_1_10
I also have a personal code where I would not wear workout clothes with co-workers, unless all female. I agree with the comfy NYDJ pants and perhaps a button up blouse. I would not pack a t-shirt, too casual for pretty much any occasion. I might wear some comfy slippers if they were spotlessly clean.
a coworker of mine brought seersucker pajama pants for this purpose. then the head of the firm invited us to a fancy dinner one night and we didnt have time to change. but no one who didnt already know noticed he was wearing pajama pants.
Yeah I don’t really understand this but if I’m on the road and working late with others, it’s at a client site. I wouldn’t feel comfortable wearing anything but work clothes. I’d consider uggs for after hours but that’s it.
That being said, my regular business casual is pretty comfy. I’m currently wearing Express pants, a gorgeous emerald green sweater from Target and JCrew Cece flats. I could wear this all day except my feet might eventually hurt.
So basically if I were starting the day in a suit, I’d opt for a pantsuit and if I wore heels, I’d switch to flats or something immediately after hours
I bought the Vince Camuto ponte pants after they were rec’d here, and now I want to wear them to work every day (I’m in academia). Sooooooo comfortable. They sound perfect fro something like this with a t-shirt or a dressier shirt if you can’t change your shirt after court.
http://shop.nordstrom.com/s/vince-camuto-ponte-pants/3242815?origin=PredictiveSearch-personalizedsort&contextualcategoryid=2375500&fashionColor=&resultback=0&cm_sp=personalizedsort-_-searchresults-_-1_1_C
Ohhh, those look nice!
I would definitely opt for black knit pants (ponte or a thick yoga pant) or black jeans and some black flat shoes, like a ballet flat or some type of little black athletic shoe (I have Puma slip-ons) that would be versatile to wear at the hotel, late nite at the war room and even out for drinks/dinner. I know black can be boring, but it’s the easiest to dress up and/or down when travelling.
TravelSmith and a few other places carry what they call a “travel” set of mix-and-match knits that looks comfy and professional. Might be a little more upscale than the yoga pants.
http://www.travelsmith.com/tres-elegant-knit-three-piece-set/women/pant-sets/466531
http://www.chadwicks.com/item/85052/407000/four-piece-jersey-wardrober-womens
http://www.chicos.com/store/browse/shelf.jsp?cat=Travelers+Featured+Collections&subCatId=cat40050&catId=cat40010
http://www.jjill.com/jjillonline/callouts/callout.aspx?pfid=285&sourcecode=11570&fid=78414124&utm_source=msn&utm_medium=cpc&utm_term=women's%20travel%20clothing&utm_campaign=Travel%20Clothing
Sorry, the Chadwicks link is
http://www.chadwicks.com/products.asp?sku=85052&cat=404504604&t=women's_four-piece_jersey_ensemble
I attended a several week client with one senior partner and another associate. I typically wore jeans and a clean comfortable shirt to work late night. I’d typically wear my suit, sans jacket, to dinner. The partner (and older male) wore jeans and a sweater and drank scotch during our late night planning meetings.
This shouldn’t be so hard. Just wear the same outfit you had on for the trip over, assuming you weren’t already in a suit. For myself, this would leggings/ tunic/ cardi/ flats or jeans/ stripey T/ flats, but ymmv.
New York & Co makes dress pants out of a stretch knit that feels like pajamas. They are ideal for this sort of situation (also travel). I can’t remember the name of the line, but you will know them when you find them.
Personally, I would wear jeans or athletic pants. Or have you considered a maxi skirt? I know the Corporette consensus is that maxi skirts don’t belong at the office, but this is not the office.
I can’t imagine wearing yoga pants anywhere outside the studio or my home. I would suggest for dark jeans with a comfortable top but, personally, I would go with a looser sweater dress. There is nothing more comfortable than a soft, loose (as in not tight) dress that allows you to move, doesn’t show anything inappropriate and makes you feel good no matter what.
Kat is right – Athleta has a new line, I believe called the city pant, maybe three or four styles that are designed to be worn in both a workout and around-town setting. Took a look in the store, some are definitely more casual than others. They also have yoga/running pants that are thick and “fancy” enough to actually be worn under a sweater dress like leggings. (Also a great packing-light approach for traveling in general.)
I lived on the road 5d/week as a management consultant, and consider myself a bit of a packing pro. I loved Misook and had a knit skirt and pant that could mix and match with just about everything and was comfortable enough to wear on an overseas flight or a late night work session with my partners and colleagues at the hotel. I couldn’t afford to wear jeans or sweats, as you never knew who you’d run into. Once I was in the lobby of the hotel coming back from a late dinner and got called into drinks at the bar – with the client’s CEO and my lead partner.
Cardis, comfy but professional tees, lots of black and white were key, as well as comfy attractive loafers. A scarf or two can really make a difference.
I second the point about the scarves.
I know that you want to feel comfortable, but would your male colleague pull of sweat pants in such a situation? If yes: go ahead. Otherwise, strive for balance between comfy and dressed up. I love viscose dresses for that reason, as they look polished, but feel almost like a pijama. They are also very versatile. You can also combine sweater/cardigan with ponte pants. Pair of comfortable flats (I’d opt for loafers or ballerinas) would also add to comfort.