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Ask The Edit: What Boss Hosts an Office Pool Party?

Dear Belle,

My boss of two years sent an invitation to his home for a pool party.  Yes, a pool party.  Just thirteen lawyers (and families) enjoying his new pool.  Setting aside that this is clearly so he can show off his new multi-million dollar reno to the other partners, what in the name of Mary and the Saints am I supposed to wear to a work pool party?  I’m 33, packing a little extra in the middle (what lawyer isn’t?), and I haven’ been in a swimsuit in two years.  Shorts are also completely out of the question for me.  And did I mention that I will be the only woman there who is not a wife because the other female associate is on maternity leave?  Oh, and my boss’s wife owns a popular workout chain and looks like Christy Turlington.  #fml 

With Regards, JD in a Bikini?

The only thing more amazing to me than a boss that equates morale boosting with pool party is how many of these e-mails I get. I was just in D.C., and heard from two people that their bosses also think an “Office Pool Party” is the perfect summer activity (or the name for a bad movie).  And you just know the boss is sitting in his office patting himself on the back for being such a cool boss, while every woman in the place is silently cursing.

So what does one wear to an office pool party when one is a career-minded woman who 1) doesn’t want her co-workers ogling her, 2) wants to be seen as a ‘good sport’, and 3) doesn’t want to spend the entire gathering feeling bad about her body?

Option No. One: Swimsuit Under a Swingy Dress

LOFT Stripe Swing Dress ($60, also in tall)

The great thing about a swing dress is that it’s fun, summery and doesn’t cling to you like a needy boyfriend at a relative’s wedding.  The forgiving shape looks great on the vast majority of body types, and gives the air room to circulate in the heat.  I like this LOFT option.  Also on my list, this simple $20 option from TJ Maxx and this summery NM dress with an embroidered yolk.  Plus-size?  This striped Old Navy dress is cute.

For my first suggestion, I would wear this dress with a halter-tie swimsuit, either one-piece or bikini.  This way, you can see the bow peeking out of the neck of the dress.  It’s like saying, “Yes. I understood this was a pool party.  Yes, I wore a swimsuit.  Yes, I’m a team player.  No, I’m not getting in, because let’s be real, neither are you.”

Add a fun panama hat, a good pair of sunglasses, and cute sandal or wedge, and you’re done.

Option No. Two: Poolside Glamour

Rachel Pally Caftan ($85)

If you want to make a splash at your office pool party, I recommend the always glamorous caftan.  This Rachel Pally has a soft neutral palette.  I also like this shorter, tassel trim caftan from Off 5th.  Or to really channel your inner Liz Taylor, try this Melissa Obadash caftan.

I would add a chic flat sandal in cognac leather.  I would also wear a long pendant necklace, like this gorgeous Kate Spade.  Get a pair of big cat-eye sunglasses, and rock it out.

So why a caftan?  A swing dress is a fun, casual way to blend in.  A caftan is a glamorous way to stand out.  If you think the other female attendees will be decked out playing the plus-one card, it doesn’t hurt to step up your game.

An office pool party is basically just a fun way to torture your employees.  You strip away any air of professional attire, add playing (yelling) children, pour on alcohol, serve cheeseburgers, and expect it not to be a fiasco.  But at the same time, this is your job.  So no matter what you wear, monitor your alcohol consumption, remember you have to see these people on Monday, and try to have a good time.

LEAVE A COMMENT

    24 comments

  1. stephanie says:

    OMG no swimsuit. Summer dress of some sort and sandals. I think there’s a good chance that the only people in the pool will be kids. If anyone says anything about you not swimming, just be like, yea no thanks and go get another drink.

    May 31, 2017/Reply
    • Belle says:

      See, I’d wear one, but cover up, and never go in the water. I went to one three summers ago (?), and all the women had swimsuits on, a couple went in the water (with their kids). I think things are just more casual out west.

      May 31, 2017/Reply
      • stephanie says:

        I’m in Los Angeles (4th gen native of CA) and 100% would not wear a swimsuit.

        May 31, 2017/Reply
        • Belle says:

          I’m not saying your wrong. I’m saying, I’ve been to one of these, only one woman did not have a suit on, and half of them were in the pool. All of them were either the judge’s employees, or the +1s of his employees.

          May 31, 2017/Reply
  2. Chelsea says:

    My former boss also threw a pool party at his home. Not coincidentally, he was an obnoxious person overall and a horrible manager. I am overweight and was the only woman there without washboard abs and fake boobs.
    The city where I live now has a vibrant music scene, so I decided to pop by with husband in street clothes, grab a beer and then leave as we were “going to a concert.”

    May 31, 2017/Reply
  3. Bonnie says:

    Lands End has wonderful swim dresses and swim dress tops to be worn with separate bottoms of choice. The fabrics are excellent quality and yes, spandex!

    May 31, 2017/Reply
  4. Chris says:

    Swing Dress with sunsuit peeking through is such a great idea! Generally, I find those dresses hard to wear. Completely shapeless isn’t great for my figure, but this seems like a way to use all those swing dresses I’ve been tricked into buying.

    May 31, 2017/Reply
  5. Allison says:

    My former boss threw an office pool party as well. Everyone wore what they would have worn had it just been a BBQ, sundresses etc. The only people that got in the pool, or even had swimsuits on at all, were children. He tried to get a few adults in the pool, I said, “No thank you, I’m enjoying talking to everyone over here by the grill. Thanks for having us over!” (Don’t blame not having a suit, he tried to convince someone to borrow one from him, ugh.) Hopefully that helps!

    May 31, 2017/Reply
    • Belle says:

      Gross. Borrowed suits, gross.

      May 31, 2017/Reply
  6. SL says:

    I’m a DC lawyer, and one of the directors at my firm threw a pool party last year. I was unable to attend, but from what I heard after the fact, it was only children who got in the pool. Everyone else just enjoyed the barbecue aspect of the party.

    May 31, 2017/Reply
  7. MB says:

    An office pool party sounds like torture.

    I own that Loft dress, and it’s super comfy, but a little short (I’m 5’10” so everything is short) and fairly sheer, just FYI! I think a swing dress with the tie peeking out is a great idea though.

    May 31, 2017/Reply
  8. Orla says:

    Funny, the only time I had bosses who had pool parties was when I was an associate at a law firm. I remember not wearing a swimsuit but getting thrown in by a fellow associate. Fun.

    May 31, 2017/Reply
  9. Valerie says:

    I don’t have a pool in my (old, crumbling) building, so would normally jump at any chance to swim in DC, but this sounds like the social equivalent of a root canal.

    Did anyone else read this post after the office pants question and think how pathetic these companies are to have one woman on their staff (two for the law firm if you count the one on leave, I know)? I appreciate Belle’s workarounds to all of these wardrobe dilemmas, but more women are earning grad degrees than ever before. And yet this “I’m the only person with this office issue because I’m female” story happens far too often.

    May 31, 2017/Reply
    • Belle says:

      You wouldn’t believe how often women preface their reader qs with “I’m the only woman” or “I’m one of two female managers.” I’ve gotten really picky about going into law offices for interviews where there are no senior women, esp. when you look on LinkedIn and see they have had a ton of female associates. Um, dudes, how come none of these ladies are staying/getting promoted? I don’t want to be XX cannon fodder. Thanks.

      May 31, 2017/Reply
      • Valerie says:

        Belle- I agree, it’s completely absurd. I’m in the process of finishing a doctorate in Government, and watching female colleagues/friends apply for academic jobs drove me away from that sector. They are all thriving in new positions, but the slog to tenure for professors is even tougher and more disheartening for women than men. I’d rather take my abilities and credentials to a future position where I’m *not* the only woman in an office/department/firm.

        June 1, 2017/Reply
  10. thb says:

    “The social equivalent of a root canal.” great line Valerie. I have been in the same position at a bar function the only spouse at said “pool party” and live out west. Never in a million years would I wear a swimsuit in front of my husband’s boss or my own if I wanted to be taken seriously. And guess what? The male boss who would wear a swimsuit at his own event has alternative objectives as well.

    May 31, 2017/Reply
    • Anna says:

      I would wear it under the dress, but hell no the cover-up isn’t coming off.

      May 31, 2017/Reply
      • Valerie says:

        @thb and @Anna- absolutely. I’d personally go with Belle’s suggestion of a chic caftan over a swimsuit with big sunglasses (and maybe a wide-brimmed hat if it was a particularly sunny day). Then I’d make myself a strong cocktail and sit at the edge of the pool with my feet in the water.

        June 1, 2017/Reply
  11. Anna says:

    Any suggestions on something similar to the caftan in the photo but short? The short suggestion was a little too casual, as are most of the ones I’m finding. I’m planning a trip to Cabo and love that the long one can be worn from the beach to a restaurant, but I hate maxi dresses.

    May 31, 2017/Reply
    • Belle says:

      Rachel Pally also makes short dresses, so I would search for one of those. Other brands to try would be Tory Burch, Milly, and Trina Turk.

      May 31, 2017/Reply
  12. Cindi says:

    Belle –
    Love the wardrobe workarounds for office pool parties! Perfect solutions to an awkward situation.
    Thanks !

    May 31, 2017/Reply
  13. Leah says:

    As a 17 year attorney and long time reader (first time commenter) of this blog, I can relate to everything in this post and the comments. The “only woman there who is not a wife” is sadly true in so many situations. Belle, your tips are spot on! Thanks!

    May 31, 2017/Reply
  14. Amanda says:

    Today has been a long day, and I love everything about this post and these comments. Thanks, ladies 🙂

    May 31, 2017/Reply
  15. Jill says:

    The obligatory work social event is just mean, especially on the weekend, especially when people have worked a long week. Employees deserve time off (and perform better when they have it).

    June 6, 2017/Reply