What to Wear to a “Resort Casual” Business Event in Florida?

resort-business-casualWhat do you wear to an event that calls for “resort casual” business clothing? (Or: what do you wear for business at the beach?)  Key factors: You already look young for your age, you’re at least 20 years younger than any of your colleagues, and you’ll be meeting some of them for the first time. Oh, also: The meeting is in Florida, so to complicate matters further, you’ll probably encounter heat and high humidity outside and frigid air conditioning inside. Reader C wonders:

Can you help me with suggestions on “resort casual attire” for a marketing meeting in Florida? I’ve been on my traveling/remote team for 1.5 years but have yet to meet some of the team. I am not only a young looking 28-year-old but my entire team’s junior by 20-25 years. My first thought when we say “resort casual” is maxi skirts and tropical dresses which doesn’t exactly scream take-me-seriously. I have a few thoughts on do’s and dont’s and was wondering if you had any guidance or additional thoughts. Thank you for any help!

Do’s: Ankle length slacks, flow-y top, colorful scarfs, knit pencil skirts, flats, cardigans
Dont’s: Sandals, maxi skirts/dresses, tank tops, pumps, blazers, tights
On the fence: Jeans, white pants, wedges

Reader M has as similar question, although this one involves a party that’s part of a trade show:

Hi! I live in Roanoke, VA, and am attending a Vendor Show in Orlando, FL, next week. The second day of the show, there will be a “Dinner & Beach Bash.” What should I wear?

We talked about a slightly different dress code, “resort chic” (who makes these things up, anyway?) a few years ago, and also what to wear to an office pool party (cringe), but not this exactly.

I think part of my answer hinges on what your regular office culture is, as well as what your regular workwear is.  Someone who normally wears crisp button-front blouses and fitted sheath dresses will wear something very different from someone who wears asymmetric Helmut Lang-type tops and Theory track pants (the track pant trend is worthy of a post in and of itself!).  Some general tips on what to wear when conducting business at the beach:

  • Figure out what the status quo is.  Ask other women, and/or see if you can find pictures of previous events. If you know the location of a particularly tricky event (such as in Reader M’s case), call the event space for tips on what to wear; they can also give you information on what’s being served.  (Sit down dinner with serious menu vs. buffet-style vs. quirky/fun menu all say very different things to me, fashion-wise.)
  • Think modesty — it’s a business retreat, not a honeymoon.  It sounds like both Reader M and Reader C are already thinking along these lines, but: be mindful of cleavage and hemlines, of showing “unusual” skin (e.g., dresses with odd cutouts) — even of wearing non-opaque white pants.  Reader M may want to review our post on what not to wear to black tie events — if she still doesn’t know what to wear after the first tip (talking to people/looking for pictures), I would get a very modest maxi dress and plan to wear that.  Along similar lines: exercise good judgement with regard to the sun.  You don’t need to have your nose painted with zinc, but I think wearing a hat, rashguard, or other sun protection can be a bit like wearing a Fitbit to the office — it silently conveys a lot about personality traits that are good for business, such as being educated, health-minded, and cautious where appropriate.
  • Make the upscale choice where possible.  For example, while I wouldn’t say flip flops or sandals are totally out, I would say that if you have a choice between your Old Navy flip flops and your leather Manolo flip flops… well, choose the Manolo.  Ann Taylor actually has a whole resort business category (which isn’t to say I agree with EVERYTHING in it, but it’s a good starting point that you can dial up or dial down depending on your personal style and budget).

With the above in mind, let’s take a look at Reader C’s guesses on what may or may not be appropriate:

  • “Do’s: Ankle length slacks, flow-y top, colorful scarfs, knit pencil skirts, flats, cardigans” — I think all of this would be acceptable.  I’d also say that ankle-length pants have gained so much popularity that you can wear those as well, as well as flared dresses or skirts.  Here’s some advice you probably won’t see me give any other time: If you happen to already own a knee-length pair of Bermuda shorts, you may want to pack those as well.  I would wear them ONLY after you’ve seen someone else wear them, and I would be as formal as possible with them — if there’s a choice in footwear, wear them with the same footwear you’d wear with a skirt, not with the footwear you’d choose for jeans.
  • Dont’s: Sandals, maxi skirts/dresses, tank tops, pumps, blazers, tights” — Barring some religious requirement, please do not wear tights to the beach — pants are fine.  I would actually say that some blazers (particularly linen ones or white ones) are totally fine for a formal beach meeting, and would be particularly great to help you cover up a tank top.  Regarding sandals — like I said above, I wouldn’t cross those off the list entirely, but I would try to make the upscale choice where possible.  I wouldn’t cross pumps off the list either — a nude-for-you pair of pumps can be perfect with a ton of outfits and be a great counterpart for bare legs.  One note regarding bare toes though:  while you don’t need to have color on them, your feet and toes should be at least a bit taken care of — no jagged or discolored toenails, identifiably-rough/cracked heels, etc. As for maxi dresses for business… I’m curious to hear what readers say.  I think a) if you’re pregnant or b) you have a work-related dinner and a limited wardrobe, wear the maxi dress (with different jewelry and accessories than you would for a formal dinner).  In reader C’s case — where she’s already feeling young and seems to be coming from a conservative office/personal style — I’d probably avoid them entirely.  For other women in other situations, though… if I already owned one that was modest enough to wear around coworkers, I’d pack it, along with a shrug, just in case after a day or two of meetings I felt comfortable wearing it.
  • On the fence: Jeans, white pants, wedges” — Again, my answer here is that everything depends… I’d avoid wedge espadrille shoes unless they’re brand new (they look old so quickly), but I think leather/cork/wood wedges could be acceptable.  With white pants — there are definitely office-appropriate white pants; just stay focused on how opaque the pant is (and what your undergarment is).  As for jeans… I’d agree I wouldn’t wear jeans, but only because denim is heavy and hot.  It takes up room in your suitcase and it isn’t easy to wear denim comfortably in a hot climate.

Readers, what would you wear in either Reader C or Reader M’s situation?  What do you think of Reader C’s suggested list of do/don’t/on-the-fence items? 

(Pictured: Boca Resort – Boca Raton, Fl, originally uploaded to Flickr by Charlie Anzman.)




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  1. I think almost anything from the Talbots resort collection would be appropriate, and fit in with your older colleagues. No need to buy anything new, but check it out for inspiration.

    • lucy stone :

      Agreed. I go to a lot of these events in the midwest in the summertime, and tend to wear a casual blazer and some variation on a sundress or a skirt with a print shell. I’ve never felt out of place.

  2. I love the made up dress codes. I have been invited to a wedding weekend where the dress code is “resort colorful” and explicitly states “no black.” Rumor has it the idea came from some Pinterest pictures where they look brightly different when there isn’t a spec of black in them.

    • Anonymous :

      If I received this invite, I would purposely wear black. People have a lot of nerve dictating people to wear or not wear specific colors to their wedding. Sheesh.

      • Wildkitten :

        Really? Isn’t that like 1/3 of what people do for weddings? Pick colors and dictate what other people wear?

        • Anonymous :

          I’ve never heard of anyone dictating colors for wedding guests who are not in the bridal party.

  3. LilyStudent :

    I would go for some of the nice Boden dresses like the Easy Day Dress, the Cate Dress, and the Seatown Shirt dress, and pack a couple of neutral or toning cardigans which can go into your bag when you’re outside but over your shoulders when you’re in the air-con. A good hat (you’ll know which type works with your face and hair) and you should be covered (literally, haha).

    Shoes… I have no idea. I’d probably go for flats or wedges?

  4. Anonymous :

    I was in a remarkably similar situation as Reader C a couple of years ago. To add to the confusion, our day-to-day office is quite casual but for meetings like this one – which are usually at standard conference centers rather than resorts – suits or suit separates are the expectation.

    Here’s what was appropriate in my circumstances:
    – Lightweight and generally lightly colored or brightly colored separates that could be dressed business for the meetings and leisure for the dinners and sunshine breaks.
    – Think modest but sleeveless dress (such as a jjill linen dress) with lightweight jacket with pumps and string of pearls during day, with pumps/pearls switched to sandals/scarf in room before wine-tasting and dinner.
    – Or ankle pants, colorful sleeveless shell, and lightweight open cardigan with long necklace and professional wedges for day and cardigan removed for outdoor air breaks.

    The “good” news is that most people seemed equally confused so there was enough variety in dress to allow for some error.

    It wasn’t asked, but I decided to not bring a bathing suit. Instead, I brought a casual, weekend summer dress. I really didn’t want to be in even a modest bathing suit around colleagues and figured I could read pool side in the dress if pool time would be expected. It wasn’t. No one got near the pool.

    I do agree that it can vary so, so much. I’d definitely ask around. Even getting the agenda may help, since it should include evening events, etc.

  5. BankrAtty :

    Perfect opportunity to bust out the seersucker.

    • Yes, seersucker was one of my first thoughts. If you have a suit, you could mix up the pieces. Blue/white jacket with blue linen-like pencil skirt (or pale blue dress) for meetings, blue/white skirt with bright tank top and white cardigan for other events.

      Also, Talbots has a lot of ponte sheath dresses, which I’ve worn with an openwork cardigan.

    • I agree as long as it is seasonal. I’ve never seen seersucker in January, even in Florida.

  6. Must be Tuesday :

    White or light khaki dress pants, brightly colored (orange, hot pink, turquoise) or pastel (mint, blush pink, blue) tops.

  7. I’ve been on pretty much this exact trip. Males wore jeans and a polo. Females jeans and a cute / casual top. Partner to associate level across the board. Casual cocktail dresses in bright colors for evening events. We had free time and people definitely sun bathed by the pool or went to the beach in bathing suits. No one wore shorts to meetings.

  8. Wow, I don’t envy you ladies who have to think so hard about what to wear to a retreat. Isn’t the idea of a “retreat at a resort” is to be in a relaxing environment to discuss work-related issues in a less formal manner? If you have to dress “formally” or appropriately to these retreats then it shouldn’t be called a retreat but work at a place other than your usual office. Not saying that you go in your bikini top and short shorts but gosh, what a pain. Women have it so tough.

    • Yeah Kat’s advice is way over-thinking it. I agree.

    • TO Lawyer :

      I think if you’ve ever overheard the comments that older male lawyers have made about inappropriately dressed younger female lawyers, you would disagree. Not saying that they’re right or excused but considering most of them are at partner level and have some control over your career, I would err on the side of conservative and not to be the subject of discussion.

      • Wildkitten :

        When I’ve gone to work retreats they’ve been mandatory work events where you work longer hours than usual without the reprieve to retreat to your own home and hobbies. They’re not actually a vacation.

        • Anonymous :

          “Retreat” = series of long work days. Argue the logic if you want, OP, but it doesn’t change the reality for the Readers asking.

        • CA Business :

          Exactly WildKitten, perfectly explained.

  9. Anonymous :

    Did retreat in Miami this past November.
    No black. Bright colors.
    Bring something to stay warm – the A/C was on overdrive.

  10. I work for a large software/technology company (think, like, Oracle) whose clients are insurance companies. When we go to or host vendor shows in the warm weather, we get the full gamut of outfits from our clients and colleagues. The best I’ve seen for daytime conference wear is neat, pressed, ankle lenth khaki colored pants, a sleeveless shell with removable (and often off) blazer, nice statement jewelry, and black or similar shoes. Open toe is fine for us, but YMMV.

    For our evening events, some people stay in outfits similar to the above; others put on maxi dresses with sweaters, others do more of a lighter colored linen sheath with big fun jewelry. Our marketing team goes more the colorful dress route while the product and sales teams are a little more formal/boring.

  11. One thing that was not mentioned is a soft wide leg pant. It would be great for an evening or beach bash event. Just accessorize based on the event. Also a Pashmina is a must for travel. Great for a cold conference room and casually throw over a tank.

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