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Summer Associate Events: What to Wear to the Fun-But-Wacky Office Functions

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This week, in our Summer Associate Series: what should you wear to tricky summer associate events, such as the company golf outing, the company picnic, or (quelle horreur!) the company pool party? There are always some creative team-building office functions (designed for interns and employees alike) that — while fun — are a minefield when it comes to dressing professionally.

(If anyone doubts that these events are still going on despite the bad economy: Above the Law holds a contest for the best event of the summer!)  Readers, what is the most creative summer associate event your company is holding? What was the hardest-to-dress office event you ever attended?

(Name aside, we hope this series will be helpful to ANY intern, whether you're a law student or another woman interning in a conservative office for the summer.)  Check out our previous post on general summer associate style.

Check out our Wardrobe Essentials for Work — all the reader favorites!

Some of the best iterations of the “what to wear to the summer associate event” question that we've covered through the years:

As of 2024, some of the best work dresses with pockets include M.M.LaFleur, J.Crew, Lands' End, Elie Tahari, and Boden… Some of our latest favorites are below! If you're on a budget, Quince has a great basic, this business casual Amazon dress has pockets, and Amazon seller VFShow has a number of dresses with pockets! Both Amazon and Etsy make it pretty easy to find dresses with pockets, as well.

A woman in a beige cap-sleeve dress
Quince
great work dress with pockets and sleeves in washable wool
Lands' End (exact)
fit and flare dress with pockets
Elie Tahari
one of the best dresses for work, the j.crew resume dress
J.Crew

Finally, this one isn't an office function per se, but can be a toughie in its own right — we've also talked about what to wear to work on the weekend. (This is another great time to pull out a sweater blazer, or keep one at the office!)

Some of our favorite sweater jackets for the office as of 2025 include M.M.LaFleur (the OG, the jardigan!), L'Agence, Summersalt, J.Crew, Modern Citizen, and Jenni Kayne. For budget options check J.Crew Factory and Quince.

woman wears olive green sweater jacket with shawl collar and patch pockets; she is wearing a black column of color beneath the jacket
Summersalt
A woman wearing a black blouse and white pants, holding a leather jacket
Modern Citizen
schoolboy sweater blazer from j.crew factory in color Loden
J.Crew Factory
green knit blazer
L'Agence

My $.02: I still remember my summer associate summer fondly! I only just recently found the map of the estate that I got for our version of the company picnic/pool party (held at a partner's house), and for some reason I always love this picture, taken after our fishing cruise.

My firm hired a boat to take us to the Long Island Sound, and the whole trip was summers-only (plus our hiring department) — it's one of the only times in my life that I can recall that I've a) gotten tipsy before 11AM (it was encouraged! honest!), and b) caught a fish!

All rights reserved.

(Why yes, those are pigtails, and no, I don't recommend them for summer associate events).

Readers, what are some of the fun events happening this summer at your office? (Any new ones we haven't covered?) Which events are always a minefield for newbies to dress appropriately? Any fond memories from your own summers?

If you're working at a BigLaw, Big Four, or other large office with a large summer internship class, you may know: there are a ton of summer associate events. While these out-of-office events are meant to be fun and to help with team building and office culture, though, they often present a quagmire for young women professionals -- what should they wear to the office pool party? How can they look professional as a golf newbie? How can they stay warm at the sailing event in May? We've addressed all of these events about summer associate events -- and round up our best advice right here!

35 Comments

  1. Pool parties are definitely the hardest to dress for. So awkward to wear a bathing suit in front of your colleagues but you also don’t want to be that person sitting on the side fully clothed while everyone is in the pool. A cover-up (or for guys, a t-shirt) is a must – I’ve been to office “pool parties” where nobody goes near the pool. For bathing suits, I try to wear something as “sporty” and u$exy as possible. The more you look like you’re on a competitive swim team, the better, I think. It’s awkward no matter what though.

    1. Oh, man. I thought trying to dress for a working meeting at a vacation resort was hard enough (which, btw, confused everyone and we were a bizarre hodgepodge of outfits). I can’t imagine a pool party. ACK! ::so thankful my office does a picnic::

    2. We do a summer office pool party/bbq and I’ve never worn a bathing suit. I just wouldn’t feel comfortable in front of my coworkers/bosses in a bathing suit. I usually wear a summer dress and sandals and hang out.

      In my experience, if any women do wear bathing suits (and they rarely do), they tend to be the assistants who often dress inappropriately anyways. I’ve never seen a female lawyer at my firm in the pool.

    4. Not a companywide pool party, but a situation with many of us knowing we were going to be stranded somewhere warm in the middle of winter after a meeting and had a day to kill thanks to not many flights–so everyone decided in advance to hang at the pool. It is really weird being around coworkers, but it was seriously a fantastic day and I’m glad I didn’t skip it to hang elsewhere. For swiming suits, most opted for modest one pieces that looked more gym than vacation or tankinis with swim skirt (highly recommend–easy to put on a shirt and feel somewhat dressed). All wore coverups as well. One person did wear something really shiny that was a mix of a bikini and one piece (hard to describe)–and I overheard comments that she looked like a Real Housewife. So, yes, def better to err on the side of fuddy duddy.

    5. I still shudder with shame when I remember my first office retreat. It was at a tropical beach resort, and 22-year-old me blithely ran around in a bikini or nude colored one-piece. Ack!

      1. I think this would be a hilarious threadjack, actually : what is your worst personal fashion disaster moment when you were first starting out in your career?

        Mine – a cotton sundress worn with a cotton cardigan that I tied under the bust. BigLaw. Seriously. It was a Friday, but still…

        1. I wore something similar to a boat outing on my first job out of college. It was a cotton sundress with spaghetti straps that I bought at Contempo Casual. It was also quite short. I threw the tiny cardigan over it thinking it would help, but then took it off when I got into the sun on the boat. So embarrassing. So not work appropriate.

          I also used to wear big platform shoes / boots to that same job (think late 1990’s Steve Madden chunky shoes).

  2. The baseball game link goes to a post about what to wear for working out in front of your coworkers – are you sure this is the right post? I was thinking more along the lines of attire for attending a baseball game with coworkers…would that fall into the picnic category?

    1. Yes, this is a sensitive TOPIC! FOOEY! I had a pool party at the manageing partner’s last year where EVERYONE had to wear a batheing suit, and then peeople drank to much and some got into a SPAT in the pool, and one guy (who shall remain namless) had his bottom’s pulled down in the pool and everyone “SAW” everything! FOOEY! It was NOT profesional, also b/c the men were stareing at my boobies and Lynn’s boobies and tuchus (she was more SVELTE last year). This year, she will be with Mason (and she is chunkyer then ever) and the manageing partner said we will NOT have a pool party but a boateing outing where shorts are requred. That way, the men will NOT be stareing as much, and we will NOT have to wear batheing suits that show just about everything. I do NOT like getting bikini waxe’s and the manageing partner’s brother will be there and this year I think he will be stareing at me more w/o his soon to be exwife there.

      Butch called and want’s to meet today. I think I will have him come here and we can WALK uptown. I think he is my best bet these day’s, as there is NO one else, except for Harold and his dad, who are fighting over me. FOOEY!

  3. FYI, the golf skirt pictured appears to no longer be at 6pm. Bummer, it’s cute.

  4. Ooh, I agree – not a fan of the c*cktail dresses in that post at all! Honestly, maybe this is boring, but for that sort of thing I would just do a sheath dress in a more dressy fabric with some bigger jewelry. This way it’s still a work silhouette but you’re a little fancier than usual. And, if your budget is tight because you’re spending it all on regular work clothes, I’d just dress up a plain black sheath dress with dressier shoes and jewelry. Throw in a wrap and you’re good to go. I don’t think SAs should have to spend extra money on things they will wear once during the summer.

    1. Agreed. The key is a work silhouette but fancier than normal. So a pink short sleeved sheath would be perfect. Or whatever you would wear to a family wedding with your conservative parents.

  5. Funeral outfits… my grandpa died this weekend. I am glad he is at peace and no longer suffering.

    so I have plenty of black in my wardrobe, and I can pull something together but my mom on the other hand… She is a school teacher (read: wears things I think are ugly) and she needs a new outfit any one want to shop for her? She is a petite (5′ 1 size 14), she will not wear a dress. The funeral is in Florida so it will be warm and humid.

      1. just pants. I have been looking online and not really finding much that’s not a full suit. Plus the Eileen Fisher/Joan Vass stuff that is too summery

    2. JJill and Talbots both have petite linen pants, at least online, in black and black summer weight sweaters. Do they need to be solid black? If you have a CWC near you (or her) that is still open, they may have something as well, marked down. I’m probably close to your mom’s age, and would wear any of those 3 brands, although I wouldn’t wear black to a funeral.

      1. Also, Kohls has a number of cheap black pants in her size, if you think it’s something she won’t be able to wear again.

    4. You don’t happen to have a cousin who lives in Phoenix, do you? Same circumstances. Either way, my condolences to you.

  6. I’m in Vegas for a training that starts tomorrow morning. I have all day today to myself and then I’m supposed to meet my supervisor and other coworkers for dinner. I’m not sure where we’re going. Would it be awful if I wore a maxi dress with a cardigan to dinner? I brought biz casual stuff for the training but didn’t bring not a whole lot of casual stuff.

    2. I probably would not wear a casual maxi dress to a dinner out in Vegas, but if it is on the elegant side it’s probably ok. If the dress is casual, I think better to wear your biz casual stuff and accessorize. Or go shopping today!

    3. YMMV but this happens to me all the time. I just text my boss or someone else that would know and ask where we are going (or what type of place). If clients are going, I ask specifically about dress code if I’m not sure.

    4. I second pregomama. I would just check with your boss or co-workers and see what they are wearing. If you are concerned about not being dressy enough for whatever restaurant you wind up at, a maxi dress is perfectly fine for 85% of the restaurants in town.

  7. I was once asked to attend a company sponsored trip to a farm. Activities were to include milking cows, baking bread and “bog hopping.” So glad I had a reason to say no,.

    1. That honestly sounds like a lot of fun. Great way to rawr at the hilarity sure to ensue.

        1. I also grew up on a farm and would love something like this. In fact, now I really want to go walk through the freshly tilled garden.

  8. Our local bar association has an annual combination event that is golfing in the morning, and target shooting in the morning! 16 different types of weapons, from six-shooters to an M16, with a local law enforcement or military “handler” for each weapon … even as a bleeding heart liberal I get excited to brag about how I’ve won the handgun competition for a few years now! (Not trying to start a political debate, just acknowledging the humor in it…) :)

    After a few years of trying valiantly to figure out the dress code, I now wear jeans, sneakers, and a (nice) polo or t-shirt.

  9. I always struggle with this. I travel for work and a lot of us will change after work and meet up for dinner later. It’s not that complicated until summer hits and it could be 90-100 degrees wherever we are. Then I just want to wear shorts but I don’t want to wear them around coworkers. I’ve settled for jeans or cropped pants and a light flowy top.

    We also have a summer outing every year that’s outdoors and very laid back. Lots of girls in maxi dresses last year which is fine, provided they have straps imo. I just wear something trendy but not over the top. Still avoid shorts unless I find a longer inseam that looks okay on me. What’s the shortest inseam that’s acceptable? Is 4″ too short?

  10. We have a firm retreat coming up. I am bringing a modest tankini. I wouldn’t wear a bikini anyway (stretch marks) but even then, I am dreading the idea of wearing a swimsuit anywhere near my colleagues.

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