Comfortable Workwear for Late Nights

Comfortable Workwear for Late Nights at the OfficeReader A wrote in with a great question that we haven’t talked about in a few years: What is the most comfortable workwear for late nights at the office? Here’s her question:

I’m starting my first biglaw job at a business formal law firm in NYC and would love to see a post about “comfortable” workwear, especially for late nights and weekends. For example, I bought the Betabrand dress yoga pants and am a big fan. I’m curious to hear about particular fabrics or brands known for being less constricting/more “cozy”. I would love to hear thoughts as to HOW casual is appropriate for late nights (e.g. can I change into leggings and a cardigan at 1am?)

Great question. We talked about working late and professional clothes before, what comfy clothes to keep at the office, and what to wear for a weekend in the office — but it’s been a while. Readers just had a great threadjack about super comfortable work clothes, as well, so let’s discuss.

My default rules, at least when I was junior, were that a) as soon as my secretary left for the day, I could get more comfortable, whether that was to take off heels and happily pad to the printer in flip flops if I needed something, or to take off skirts or dresses entirely and put on yoga pants and a black t-shirt. A couple of points that should probably be noted: a) my office culture was one of a lot of closed doors, so it really was just trips to the printer or the bathroom where I might run into colleagues, and b) everything I changed into was black, opaque stuff — no crazy patterns or mesh cutouts. This isn’t to say that you CAN’T wear that stuff, just that when selecting the default stuff you keep at the office, maybe choose the conservative option. It’s probably also worth noting that I didn’t change into more comfortable clothes every night at work, because I didn’t consider every outfit to be so uncomfortable that I needed to get out of it, and there were definitely differences between nights when I knew I had 6 hours ahead of me of document-intensive work and would need to stretch out on my office floor surrounded by piles of paper and highlighters and notes; regular nights where I thought I could get out by 8 or 9, or was meeting friends afterwards; and nights where I was working in conference rooms with other people or running around and managing other teams where it just didn’t occur to me to go put my comfy pants on.

As for WHAT to wear, I think these days you have a lot of options in addition to the classic yoga pants, from pull-on ponte pants that might be comfortable and appropriate enough to wear all day (readers were just singing the praises of these Lands’ End ones as their “holy grail ponte pants,” as well as NYDJ ones*), to more traditional leggings (I’m a big fan of the Hue leggings* for opacity, durability, comfort, price, etc.), to comfortable jeans/jeggings. (I also have the readers to thank for turning me onto the pull-on JAG jeans*.) Know your office, but I think the conservative take on “I might be going to or coming from the gym” might also work for weekends or late nights — by “conservative take” I don’t mean sports bra + running shorts or “strappy sexy yoga bra + leggings with daring mesh cutouts” — but again, know your office. (I say “daring mesh cutouts” because there are definitely some that seem more… well, daring… but obviously it’s hard to find workout leggings without mesh cutouts of some kind these days.)

Over to you, readers: What do you consider to be comfortable workwear for late nights? What do you think is off-limits — and what factors would influence your decision to change or not change on a particular night? (Slightly off topic, BUT two more Qs: a) what’s your opinion on mesh cutouts/gym looks, and b) do you think it’s ever acceptable to put on a “comfy bra”? The closest I have in my closet to an “18-hour bra” right now is the shorter version* of this one, so I might choose that one at the beginning of the day.)

* – This post contains affiliate links and Corporette® may earn commissions for purchases made through links in this post. For more details see here. Thank you so much for your support!

Picture via Stencil.

What is comfortable workwear for late nights at the office? Can you change into leggings after 8PM, should you wear comfortable clothes at the start of the day, or should you just tough it out in your sheath dress and Spanx? We've got some thoughts...



  1. My biggest issue in working off hours is that they turn the HVAC off. If it’s cold, I can and do wear my coat in addition to my office pashmina. If it’s hot, what can I do? I can’t strip down, at least not that much.

    The only clothes I really keep at work are sneakers and flip flops and some pashminas. The flip flops are for getting a pedicure. The sneakers are for short exercise walks or if needed in case of evacuation. The pashminas I use all the time due to aggressive air conditioning (when the HVAC is on)

    If I come in over a weekend it’s a different story. I tend to wear whatever I would be wearing for the weekend. However, I’m usually only in to quickly grab things needed to work from home, or to use the printer/copier/scanner. I don’t spend more than an hour or so there.

    • On the bra issue, I don’t understand why that would be a weekend only / questionable for weekdays bra. It looks like a really normal bra.

    • I like to be comfortable if I am busy working at home after I eat dinner. So I change into my PJ’s and slippers and then turn on my MacBook Air so that I can be efficient at my billing. I think that the manageing partner likes it when he sees me billeing all of my 150 hours each week, so that I can stay on track for my yearly goals. This month, I am a little behind, but I expect to catch up in the next 2 weeks so that I can take 3 days off at the end of the month and leave my MacBook Air at home when I go to Disneyworld! YAY!!!!!

    • Coffee Queen :

      I wear jeans and a hoodie if I am going to be there long. Our office runs cold and I want to be comfortable. Most people don;t care what we wear afterhours and I have seen associates where pj pants.

  2. I don’t think mesh cut outs on any clothes should ever be worn at work.

    It never occurred to me to keep a change of clothes for late nights but I can think of many examples of simple comfy pants and sweater/top that would be perfectly appropriate, if not super stylish. I’ve always tried to wear something like that when I knew it would be a long day but, of course, you don’t always know. My concessions to a late night are usually shoes (I walk around my office barefoot but it’s carpeted and my door closes) and jewelry (I find even basic jewelry annoying if I’m doing a lot of writing). I also keep cardigans and wraps in my office and would probably switch to that if I came in wearing a blazer.

  3. Hedonistic treadmill :

    I’ve been thinking of the hedonistic treadmill / ratcheting up of needs phenomenon. In our materialistic world, one purchase leads to another and I have a resistance to this type of coercion from marketers.
    For example, most clothes are polyester or synthetic blends. If I wear non-cotton, it doesn’t absorb sweat and I need strong antiperspirants. Then you need to spend on dry cleaning the clothing item.
    Same with makeup. Do we really need eyelid primer before eyeshadow or are we falling for a marketing myth? Then do we need makeup remover to remove the (now waterproof) makeup items we’ve bought?

    Do these items really improve the quality of our lives or have we been brainwashed into thinking they do and we “need” them? Maybe all they add is toxic chemicals to our bloodstream and increase the risk of various diseases.
    Did we “need” a front and back camera on phones or could we have managed to just swivel the darn phone to take a picture?
    But for my husband, who is all about that latest gadget and cool vacation, I think I’d live a life of a forest ranger, off the land and do yoga in my cotton clothing.
    Talk me off the ledge folks.

    • I mean, we don’t need sliced bread but it sure is nice…innovation is part of human nature.

    • For me, eyelid primer makes my eye shadow last longer and not crease. So yes, it does improve my life a tiny bit if I want to wear eye shadow. And there are times when waterproof mascara improves my life a tiny bit, so I need the makeup remover to take it off. Have I been tricked by society into wearing eye shadow and mascara? Maybe, but I know I want to wear them, not need to.

      Maybe something bigger is stressing you out and you are projecting it here because these examples don’t seem like a big deal to me. There are definitely things we don’t need that we often feel pressure to have anyway (big house, fancy car, the newest gadget) but I’m not sure eyelid primer and synthetic clothes fit that category or are some big conspiracy.

    • Anonymous :

      I agree, OP. I too would like to live a very analog life in a cabin somewhere.

    • Anonymous :

      I mean do what you want. But I don’t feel this pressure. I don’t need eyelid primer. Polyester is easy to machine wash and doesn’t require dry cleaning. Similarly I don’t dry clean things every time I wear them. There’s a lot a lot a lot of space between buying everything and living in a yurt, and generally I feel like if you’re trying to solve one problem by completely changing your life something else is happening.

      • This. OP, I get where you’re coming from, but I think you’re falling down the rabbit hole a bit.

      • +1

        I get the desire to examine why you’re doing something and question whether you’re just doing it because of advertising, but, also, it’s not that hard to just buy machine washable clothes.

    • Hedonistic treadmill :

      OP here – yes there are big things too, like keeping up with the joneses stuff, but that’s a different motivation I think, and a separate topic.

      The examples I chose were intended to highlight when one version of X needs you to buy Y after, whereas a simple version of X may not need you to buy Y and offshoots.
      For another example, there are plain white socks which you can buy in a set of 8 pairs – fruit of the loom perhaps. There are also sets of 8 pairs where each pair is different or have slightly different colored or patterned designs. In the second case, if one of a pair is eaten by the washing machine, then you are one step closer to buying more. Whereas in the first case if you lost one of a pair, you’d just use one of the remaining singles because they’re fungible. For kids socks I notice that the first kind are hard to find, and the second kind (Frozen theme socks with individual designs) are ubiquitous. My kid doesn’t particularly care for socks (yet!) but if the marketing works, it may become a desired feature.

      • I get what you’re saying, and in general, all of us could stand to be more mindful about purchases. I just see some of your examples as going too far into “sweating the small stuff” realm. I’m saying this as someone who has these tendencies, which are sometimes driven by anxiety or trying too hard to exercise some sort of control in my life (which often feels out of control).

      • Anonymous :

        It’s really not all that hard. Plain socks exist. Children can and do, all the time, wear mismatched ones.

      • You’re working yourself into a bit of a frenzy here.

      • With white socks, aren’t you technically still out a pair because you can only wear x-1 pairs before washing them all? Of course, if you lose two socks of a bunch of white, that is different than losing two socks each of a different type. But I don’t think there is any marketing conspiracy to get us to buy differently patterned socks so we then lose half of them and have to buy more. Besides, eventually wouldn’t you buy more white socks because even if they are still paired, you are still down a pair? Or because socks get worn out and you need news ones? I don’t see a major buying escalation here.

        Some people find a little joy in wearing patterned socks. If you value wearing patterned socks, then buy patterned socks. If you instead value having more pairs when you lose individual socks, buy the white ones.

      • Socks are really inexpensive.

  4. True story: we had a secretary that started her workday at 7 AM, and she almost called security when she turned up at 6:45 and found me wandering the halls in the leggings, an Iron Maiden t-shirt, an oversized camo hunting jacket, and UGGs (I was on the back end of an all nighter and was taking a walk to try to stay awake).

    The moral of the story is that I was of the school of thought that after about 10 PM, all bets were off in terms of office attire. This was probably in the abstract a bad idea, but ultimately, it doesn’t seem to have hurt me.

    • I’m a biglaw midlevel and I usually change between 8 and 10 pm if I’m going to be around for a while, especially if I chose something not-so-comfy to wear during the day. When I know I’m going to be around late, I’ll intentionally bring thick comfy socks which are *key*.

  5. Clementine :

    I keep black leggings, a solid color ‘nice’ tee (also my ‘oh my god I just spilled coffee all over myself’ backup) and a big cardigan at my desk.

    I change after 7PM generally. I also switch to flats, but I keep my work shoes at my desk. Also key for late nights: toothbrush and toothpaste, makeup remover wipes, dry shampoo, hair ties, and eye drops.

  6. Anonymous :

    This is a very know your office question. Ime people change their shoes but that’s about it. The only people who change their entire outfit are the ones who go home to say goodnight to their kids then come back. My secret hack is to change or remove my bra – no one can tell but it makes me feel a lot more comfortable.

  7. Why wouldn’t it be acceptable to put on a comfy bra? As long as it’s covered, who’s going to know? I don’t understand the question.

    On the rare occasion that I have to come in on the weekends, I wear jeans, flip flops, and a tee, usually. If I had to work super late into the night, I live close enough that I could go home and change and that’s probably what I would put on. The few times I’ve had to work later than usual but not into the small hours, I’ve kicked my shoes off and walked around barefoot. Bringing something to change into hadn’t really occurred to me.

  8. Anonymous :

    I had a lot of midnight filings when I worked in Big Law and I would definitely change into flip-flops or slippers as soon as the regular workday ended (by 7 pm at the latest usually). I rarely changed clothes (except maybe to replace a blazer with a slouchy and not super professional cardigan), but I only pulled true all-nighters a couple of times.

  9. Mary Ann Singleton :

    Shoes off and warm cozy socks on. That’s about all I will do, but sometimes I’ll add a warm sweater too, or a pashmina.

  10. If I knew I’d be working really late, I’d wear comfortable clothes to the office that day. Around 6 or 7, I’d switch a blazer for a cardigan and change my shoes and put my hair up. On the weekends, though, I’d just wear jeans and a t-shirt or a casual dress or any other non-workout, non-loungewear weekend attire. YMMV, but I’ve never felt comfortable in yoga pants at work.

  11. I am often working at a client site very late, so changing into yoga pants is definitely not an option for me, but I can see how others would do this in their own office space. I prefer to wear dresses that are not form-fitting (think shift dresses) so that they can move with me no matter the hour and, come 10pm, I don’t feel so restricted/uncomfortable by what I’m wearing. If I don’t wear that, I am wearing my most comfortable slacks and a loose fitting shirt, again, so that I’m not feeling claustrophobic by my own clothing as the hours roll on. I usually do a more tailored pant and a more comfortable shirt… it provides a nice balance for me working so much. I definitely kick off my heels after 6pm and change into flats or another comfortable shoe.

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