What to Wear to the Company Retreat

What to Wear to the Off-Site Company Retreat | CorporetteWhat do you wear to an off-site company retreat at a center with both a conference center and hiking trails — and a dress code of “casual”? Poor Reader M is stuck with this problem on her first day of work, adding yet another layer of complexity…

I’m starting a new lawyer job next month that I’m very excited about. I would normally wear a suit to my first day of work, but my department has scheduled a retreat for the same day I start work. I have been asked to attend the retreat, but I have no clue what to wear. The retreat will be at a facility that has both a conference center and hiking trails. The email said “casual.” What on earth does that mean!?!? Are we talking work casual, like a respectable dress with flats? Weekend casual, like nice jeans with a blouse? A sundress? How do I make the right first impression without being overdressed?

Wow.  To Reader M, my apologies — this situation stinks!  I don’t think there’s any way you’re going to get out of this without just picking up the phone and talking to someone in HR.  My $.02: pick out what you think you should wear and run it by the person during your brief phone call.  In general I think you want to look friendly, detail-oriented, and responsible, so if this were me I’d probably go with washable trousers, a “nice” t-shirt, flats or comfortable heels (maybe a wedge in case you have to walk on grass), and an accessory that looks good both with a non-suiting blazer (to be kept in your car? folded on the back of your chair?).  A good question to ask during your conversation: whether there are any pictures of last year’s event in the company newsletter or whatnot.  Another option here: call the manager of the facility and ask what he or she sees most often.  You never know — she may be able to give you extra insight into the day’s plans (such as, well, you wouldn’t want to wear X because it might get dirty during the fire walking portion of the day!).

In general, though, readers, let’s discuss — have you been to any off-site company retreats that have both a conference center and hiking trails — and if so what did you wear?  Would you dress differently if your FIRST DAY were the day of the company retreat (such a new-kid-new-school vibe, right?!)? What does a “casual” dress code say to you anyway?

What to Wear to the Off-Site Company Retreat | Corporette


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What to Wear to the Company Retreat


  1. Maddie Ross :

    To me, this is the type of situation where you 100% ask the person who told you that you were attending the retreat what specifically should be worn. If they cannot tell you or simply give you the party line of “casual,” contact a young (helpful if female) associate and ask them.

    • Absolutely agree. It’s going to vary so much by company. I read Kat’s suggested outfit above and thought that person would stick out like a sore thumb and ruin an outfit for no good reason, because my frame of reference is based on my office–where you would wear jeans or even shorts, comfortable shoes (whether that’s riding boots, flats, or tennis shoes for you), and a casual tee (think J crew perfect T, not a “dressy” tee). You’ve just got to figure out what goes in your company.

      I would not let it being the first day affect too much. I’m not saying let it all hang out and show up in that Bob Marley t-shirt you hiked the AT in–with smells intact–and ripped jeans, but more just that you don’t need to go one level up from everyone else. You should match everyone else here (because if you don’t you may stick out in a bad way and people will question your judgment if you wear heels to a hike). Save the suit for the first day back in the office.

      • Meg Murry :

        I would also ask the person you are calling whether the hiking trails are on the agenda or if its just going to be a “sit in a conference room” type of retreat that happens to be in the woods. We have a retreat at my office that is the latter – the wooded location makes it more of a getaway, and its cheaper than most urban conference centers, but hiking isn’t on the agenda and it is paved from parking lot to building.

    • West Coast Lawyer :

      Since the location also has a conference center and hiking trails, I would also ask what type of activities are planned. If you will be doing teambuilding meetings inside all day you can err on the nicer side (i.e. casual dress and flats) but if you are going to be hiking then it’s a safe bet everyone else will be in jeans or even shorts and sneakers.

    • Diana Barry :

      +100, you need to ask the department head what the schedule is going to be and see if you can ask an associate as well.

    • +2 ask an associate if you can.
      I attended a retreat where there were sporty activities planned (optional), so I mistakenly assumed that nice dark jeans and a button-front shirt for the rest of the time (meetings) would be okay. Nope. I don’t think it actually mattered, but there was maybe one (out of a couple hundred) other person in jeans.
      And our firm dress code is technically business casual.
      I do think that one reason it didn’t matter was that I normally err on the dressier side at work… so people at work don’t think of me as too casually or sloppily dressed. Since this will be the first impression people have, I’d definitely try to ask someone who’s been to the firm retreat before.

  2. IDoNotLiketheConeofShame :

    If for some reason she does not get any specific or helpful advice from her contacts, then I would go with a nice dressy jeans / blouse / cardi or jacket combo with flats/nice tennies/boots. Layering for indoors and outdoors, plus the cardi/jacket could serve to dress you up a little when sitting in the conference center.

    No skirts, dresses or heels in case of hiking or ropes courses or trust falls. Ugg, what a horrible way to start a new job, happened to me once, and I was very self conscious and wierded out.

    • TO Lawyer :

      I like the jeans/blouse idea with flat shoes. Or alternatively, for a bit of a formal look, you could wear skinny ankle-length pants – maybe even in a nice colour?

      I would stay away from dresses and skirts (even though they would normally be my first choice) because they give off a more formal impression and you don’t want to be seen as the associate who can’t follow instructions (even though this is really weird and frustrating).

  3. I’ve been to three retreats at just such a place! It’s usually casual–think jeans and some sort of flannel or plaid shirt. Maybe a polo and jeans. Just don’t make the mistake one associate did of wearing leggings in lieu of pants–yikes!

  4. I do think that if you wear flats or comfortable heels, you should be bringing shoes you can walk on the hiking trails in without looking ridiculous.

    • Agreed. Even if people don’t hike, there could be some other “sporty” event (like an impromptu game of volleyball, or Frisbee toss). Definitely bring a pair of comfortable shoes.

  5. I agree that without knowing the office, the only way to figure out what’s appropriate is to ask someone. Congrats on the job, and at least you’ll always remember your first day!

    If you can’t track down an answer, I’d go with Cone of Shame and wear khakis or dark-rinse, well-fitting jeans; a classic yet non-stuffy t-shirt or collarless blouse (something that won’t wrinkle, doesn’t need to be tucked, can layer) and a cardi or similar for layering inside. For shoes, maybe flats or oxfords.

    I went away to a summer conference in July at a similar resort: all-seasons, rugged-y, but serves a very affluent DC-vacation population. Most people wore business/casual during the seminars & such, but there was more casual dressing by some, and presenters wore dresses/skirts or ties. I don’t think I saw any full suits. I wore khakis, sandals (and my keens), dressy t-shirts, cardis & scarves. It was frigid inside, and reasonable (but humid) outside. There was to be zip-lining/rock wall & such at the meet-greet dinner on the first night, but it was rained out. Everyone was dressed more casually than daytime, though.

  6. My 5 cents :

    Think of this as your first impression, not your first day. You want to blend in, not stand out in a professional suit. Definitely call the person who emailed you about the retreat and ask what folks have worn in the past. My suggestion is dark wash jeans, a nice polo or button front shirt with the sleeves rolled up (like a camp shirt), and a cardigan in case you’re cold. For shoes, I’d wear boat shoes. I’ve been to a few retreats at similar places. While we only did outdoorsy activities once, everyone still dressed ready for the outdoors. No heels or dresses! You don’t want to appear high maintenance.

    • I only wear skirts & dresses, and on my second day at a new job there was an afternoon picnic scheduled. I guess the impression I made was that I only wear skirts & dresses. (I did change into athletic shoes).

  7. Because it’s not a retreat that’s only for people starting that day and M is just starting, I’d dress “+1 level” (as it’s sometimes called in the Silicon Valley when lawyers meet with engineers). I’d guess that most people would wear jeans, flat shoes/sneakers, and a polo or business casual short sleeve t-shirt. To “+1 level” that outfit, I would go for dark jeans or slacks, a more formal shirt, add some jewelry, and wear more formal but still appropriate shoes, like wedges. In case of AC in a conference room, I’d also pack a cardigan.

  8. Anonymous :

    My law firm does an annual summer retreat at a ski resort – our agenda is meetings in the morning and then group bonding activities in the afternoon. People’s dress ranges from Friday casual (dark jeans, blouse, cardigan, and flats) to weekend casual (t-shirt, modest shorts, and sandals) depending on what activity they plan to participate in (hiking, golfing, fishing, bar crawling, etc.)

    • This is exactley what I would wear. It alway’s pay’s to ask first, if there are OTHER women in the firm, but you should have a VARIETY of clothe’s to wear in case there is something more formal then you think. At my firm, we have POOL partie’s at the manageing partner’s house in the HAMTON’s, so we know we have to have batheing suit’s, but we also do other thing’s so we have to wear clothe’s too. I alway’s come with dark jean’s and flat’s b/c it is dumm to be walkeing around the pool in pump’s — how silly would that be, and I never wear tee shirt’s, stricley button down collared shirt’s that have LONG sleeve’s that prevent the SUN from burnening my skin. Madeline helped me the first year, and now I am a partner and she is not so I feel bad some times about that. FOOEY b/c she could be a partner if she onley had a little more MOXIE, like me! YAY!!!!!!

  9. I think the best thing you can do is first ask for clarification on the agenda and then ask for more details about dress. I’d have two outfits in mind, one for a picnic/boardroom retreat and one for an active retreat, so you can run it by the person you’re speaking with. When in doubt, go slightly dressier and throw something extra in your car in case you need to swap out your shoes.

  10. My first step would be to call the place holding the retreat and ask to speak to a manager. They may have a ton of info for you if it’s an annual event. Even if not, they may know what’s on the agenda (conference room meetings or everyone hikes up a mountain for a picnic lunch).

    As for how to dress, I always think of those inherently formal people I know (the ones who always look tidy and freshly starched) and think “what would they wear”? Or picture Carolina Herrera at one of these things. Whatever works for you. I’d probably opt for pixie pants, a non-too dressy button down and a casual blazer that could double as a jacket and comfy enough shoes for a hike — if it ends up being more formal, tuck shirt in and put on blazer. If it’s less, keep shirt untucked and leave blazer aside.

    • You could even wear a casual tee underneath and take off button down if it’s really casual and tie around your waist.

    • I always go with “What would Kate Middleton wear?” and then dress accordingly.

  11. +1 on get the schedule. If you’ll be coming from the office mid-day more business casual makes sense. If you’re immediately getting on a ropes course, you’ll want to know this.

  12. I definitely agree with some of the comments above, casual would definitely be the way to go. Someone mentioned to ask for the schedule, great idea! I would opt for some dark wash trouser jeans and a lightweight blouse. I would probably carry a lightweight blazer to dress it all up while indoors. Thanks for a great post!

  13. Having recently gone hiking pants shopping, there are some remarkably trouser-like ones readily available at REI and the like that might be good options for pants that can pretend to be business casual but can be moved in like jeans (or frankly, like yoga pants. Active wear pant technology is impressive). Stay away from the cargo-type ones and it could be fine. PrAna and Columbia had some cute ones.

  14. lawsuited :

    I think black jeans with a casual blouse/”nice” tee with flat shoes is a good bet. Take running shoes with you and leave them in the car.