2017 Update: We still stand by this advice on what to wear when you need professional clothes for working late, but you may also want to check out this recent threadjack from readers on what to wear to be super comfortable at work.
What should you wear when you’re planning to work late — and you’re traveling? 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. 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. (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.
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. There are even “yoga pants for work” (I believe both BetaBrand (pictured at top) and Athleta sell ’em), ponte pants (such as those from Lands’ End — I know readers were just recommending one of their particular fits and will update this post when I find it), or just generally comfortable/stretchy pants (such as Gap’s washable wool trousers). (I’ve even seen readers singing the praises of JAG’s pull-on jeans, although I have not yet tried them myself!)
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).
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?