What to Wear to the Office Pool Party…

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2018 Update: We still stand by this advice on what to wear to the office pool party — but you may also want to check out our recent discussion of swimsuits for professional women, as well as all of our advice for summer work events like this, including summer associate events.

What should you wear to the office pool party? Can you wear a bikini to an office function? Are women really “damned if you do, damned if you don't” when it comes to the summer work events like this? Reader B wonders…

My office is planning a couple “beach days” or “boat days” this summer. This will be primarily coworkers, but families may be invited to 1-2. I am the youngest person in my office by about 10 years and also one of very few females in my male-dominated company. We are a casual to business casual office normally.

What does one wear to something like this? I don't want to wear something my coworkers will be chatting about Monday, but my typical beach/swimwear (bikini + straw hat + little coverup dress) seems like it would perhaps be too risque for an office party?

After I sent her the post and discussion from the last time we talked about what kind of swimsuit to wear for an office function, B wrote back:

I don't own any one pieces (I'm 24 and just at the start of my career) or even tankinis, so I'd need to buy something if a bikini is too risque. I think part of my issue is I'd probably be one of maybe 2 women there. Most of the advice seems to be for larger offices, but I work in a small, mostly male office where I am positive if there is water, 90% of my male coworkers will be jumping in without abandon and will probably think I'm a bit of a party pooper if I don't.

The poll question also makes me a bit sad – as was mentioned in the comments, it seems like I can't win. If I go with my typical beachwear (a well fitting bikini I look OK in and is not inappropriate for a non-coworker event, covered up when I'm outside the water), everyone will think I'm inappropriate and my male coworkers might stare. Okay, fine. But if I wear a conservative swimsuit and a coverup, half the people will think it's completely inappropriate I wore a swimsuit at all. And the other half would think I'm lame for not joining in the activities? It really does seem like a question that's a damned-if-you-do, damned-if-you-don't.

Well, when you put it like that…

First, to reader B, if your male co-workers are mid-30s, I'd actually be surprised if “90%” of them are comfortable enough in their own skin to rip off their shirt and dive on in (unless, perhaps, they're taking their own children in). But let's assume I'm wrong. Since it's your first time going to the office pool party:

– Focus on wearing an outfit appropriate for other activities.  A barbecue? Volleyball game? Boating? These each have their own considerations, but I would say that an outfit appropriate for this is the primary thing you should be focused on. In other words:  your cover-up is not your outfit; it's just something to wear immediately before or after you get out of the water.

– Think “sporty,” not pin-up, push-up, or sexy.  Think “appropriate for my boss's 10-year-old son to see me in.” I always think of Land's End has having really conservative, well-priced swimsuits that can also be a bit cute; I also really like the vibe of the Athleta catalog. If you have to wear stilettos with your bikini, you're in the wrong ballpark.

– Do your best to avoid the chance of any “wardrobe malfunctions.”  For example, the J.Crew bikini pictured above has no straps and ties in the back… so even though it's really cute, I would avoid it for the office party. If you haven't worn the swimsuit before, make sure nothing's showing through. I would probably choose a top with a bit of padding on it to avoid “headlights.” If you have bikini line issues, make sure that they're under control.

– Whatever you wear, only wear your swimsuit in the pool itself.  Don't lounge on chairs and try to get a tan or anything like that. As one of the commenters noted in the older post:

We had a pool party event at one of the named partner’s homes when I was a 2-L summer associate at a California big firm. Some of the summers (male and female) went swimming, including one female 1-L who spent many lunches working out instead of going to lunch. She was in fantastic shape and looked great. She swam and also lounged a bit by the pool to dry off. She didn’t do anything that would have been inappropriate at an in-law’s pool. … The other swimming summer (also a 1-L) wore a sporty-type black bikini while in the water, and immediately changed into clothes once she got out of the pool. … She ended up declining her offer. People still mention her bright blue bikini two years later when her name comes up. The black bikini summer also declined her offer, but no one mentions her bikini.

That said, can you wear your regular bikini? I still would strongly advise against it, if only because this is your first time at the office pool party. If you're really dead set on wearing your bikini, I beg of you: please bring a more conservative option with you to the event. It's ok if it's an inexpensive, ugly one-piece — it's even OK if the tags are still on it when you arrive at the event. That at least gives you the option to figure out the vibe of the event and decide what to wear. If you feel confident wearing your regular bikini in the water, rock it out. If you don't, though, you'll be glad you've got a more conservative option to choose from.

Readers, weigh in: what have you worn to office pool parties? What would you advise a 24-year-old just starting at a law firm to wear?