The Four Most Confusing Dress Codes of All Time

If you’re looking for the difference between formal, semi-formal, black-tie, etc, go read the Wikipedia article – they write it more polite and more concise than I ever could.

This article is not even about the obnoxious dress suggestions I see on invitations now-a-days: festive formal, creative black-tie, urban casual.

No, this article is instead about the common events I see the most panic about; the invitations that elicit a soft oh, shit from even the most dainty or cultured mouth. The moments that cause women (or men) to set down the invitation and stare at it with the realization that they have absolutely no idea what to wear.

There are probably more out there, but these are my four biggest “WTF?” moments I get concerning event invitations: the ladies luncheon, the beach wedding, the garden party, and the ever-dreaded “being invited onto a boat.”


Should you care? Well, if you’re at WhatWouldJackieDo in the first place, you probably do.

Why should you follow a dress code or a dress suggestion? First, let’s assume you’d like to be invited back. Following a dress code is all about respecting your host, hostess, or hosting establishment – it shows that you read the invitation, you paid attention, and your put in some thought. Ignoring the dress code makes it look like you are apathetic, decided to come at the last minute, don’t really care, or worst of all, crashed.

Dress codes are not about restricting people – they’re about giving a head’s up on the tone of the evening; they’re the road map to not feeling out of place.

Can you break the rules? Sure – but you have to know them first to break them later.

Ladies Luncheon Ensemble

Here’s To The Ladies Who Lunch,
Everybody laugh.
Lounging in their caftans and planning
a brunch, on their own behalf.

– Stephen Sondheim, “Ladies Who Lunch,” Company

Boy, is it ever easy to screw this up. I’m just going to put that out there – I have screwed up some ladies luncheon ensembles in my time. Now, to be fair: both the South (my origin) and the Midwest (our current place of residence that Jack perkily refers to as “the flyover country“) are more conservative than, say, the West Coast. But I also feel that, when in doubt, a lady errs on the side of conservatism.

You don’t have to be a “lady who lunches” to attend a ladies luncheon – the luncheons I’ve attended range from awards ceremonies for high powered corporate types to Junior League fund raisers. But across the spectrum, there are a few steadfast and unspoken rules that will carry you gracefully through any type of luncheon.

  1. No strapless dresses. At a luncheon of 200 women, you will probably be hard-pressed to spot a strapless dress, even in summertime – perhaps one or two paired with a cardigan, but largely, the dresses have either sleeves or shoulders.
  2. Conservative hemlines. While this doesn’t mean tea-length or longer, a ladies luncheon is not the time to show off your newest mini.
  3. Suits or jackets. Luncheons during the week take place during the business day, and are usually set to allow professional women to glide in, eat, and dart back out again. This means you’ll see a lot of women in suits or jackets. Does it mean you have to wear one? It does not, but it does make a suit or jacket a safe bet.
  4. Handbags. I see more designer handbags at ladies luncheons than I do cocktail parties, weddings, and galas combined – this seems to be the time to break out your designer stuff. Also, because a luncheon is in the middle of the day, people assume you’ll be coming from something before and going to something after; therefore don’t be afraid to bring your bigger business bag instead of a tiny evening-styled clutch. They know you’re busy.
  5. Space. That being said, ladies luncheons are usually tight on space. Typically, they’re fund raisers in one form or another, and the idea is to maximize the revenue (ahem, the amount of people paying for their butts to be in seats) across the space. This means tables of 10 as opposed to tables of 6 or 8, which means you’re going to be in closer quarters than if you were just having lunch with your girlfriends. Leave the rolling laptop case in the trunk of your car or, if you’re desperate, check it with the concierge.

Casual Beach Wedding

I loathe the phrase “casual beach wedding.” I know getting married on the beach is romantic and all, but there is not a more awkward dress code on the planet. It’s still a wedding, even if the guests are holding lavender and incense and the bride rides a magical donkey to get to the alter. Therefore the gut reaction is to dress up. Yet, it’s on a beach – with sand. And wind. And surf. So the opposing gut reaction is to dress down. What’s a girl to do?

Well, like with all weddings, snag the mother of the bride or one of the bridesmaids well beforehand and ask her. If it really is a formal affair on the beach, then you’re just screwed – wear something nice, with flats. Period. I have been to these weddings – weddings where, as bridesmaids, we were forced to wear heels and formals on rocky outcroppings, or stand in taffeta under 102 degree sun, or try to ignore seagulls unceremoniously dive-bombing everything in sight. As a guest, wear flats and bring sunglasses. Manage the coolest and most comfortable clothing you can while still being dressed up. I have a linen halter post-card print dress from J. Crew circa 2007 that serves this function nicely.

If, however, it really is a casual beach wedding (we have friends this summer who are going down to the JP to get married the week before, and then throwing a huge beach-house reception sans ceremony the next week), then you’ve got a lot more leeway. Regardless:

  1. Trade your flip-flops in for sandals or cute flats. They should be comfy sandals or flats, but still – even a casual beach wedding isn’t the time to break out your ADIDAS flip-flops you used in the communal shower at college.
  2. Stick to light fabrics. This should go without saying, but many a time have I stroked a wool or tweed dress in my closet in June, thinking “…but it’s so cute.” Don’t do it. Stick with cotton or linen, which breathe and absorb sweat.
  3. Choose flowy over body-hugging. Now, I am not a woman who looks particularly good in flowy empire-waist dresses – I am not an earth-mother or gypsy or hipster or any of those types that can pull off “flowy” like it was made for them.  But on the beach, I do flowy, because it’s comfortable, and you should too, especially at weddings. You never know when you’ll be enlisted into impromptu seashell collection, rounding up someone’s rogue puppy, or engineering the arrangement of tiki torches. Always be prepared.
  4. Let your hair go. Just let it go. It will be wind-blown. It will have sand in it. It will have sweat in it. Style it in a way that is appropriate for these eventualities.


Garden Party Ensemble

I went to a garden party to reminisce with my old friends
A chance to share old memories and play our songs again
When I got to the garden party, they all knew my name
No one recognized me, I didn’t look the same

– Ricky Nelson, “Garden Party”

If beach weddings are the most confusing of dress codes, garden parties run a close second. If you’d asked me ten years ago, “Who throws garden parties anymore?,” I would have responded with a resounding “NO ONE!”

But this is just not true. Museums with courtyards, families with large backyards or country houses, urban comrades lucky enough to have a large garden space, fund raisers on the sprawling lawns of estates – garden parties never left.

Like a beach wedding, you need to dress in preparation for being outside, but there is less wiggle-room in wardrobe choices. A garden party is not a BBQ.

  1. Keep your hemlines down. We know it’s hot. Hell, if it was up to me, people would be able to go around in their underwear everywhere in summer. But it’s not up to me – if you have to ask how long your dress should be, stick with knee or tea-length.
  2. The question of shorts/pants. A pair of sharp-looking khakis is never out of place at a garden party. Shorts are a grey area – if you do wear shorts, keep them modest and tailored. Or better yet, opt for capris, petal pushers, or skimmers. Leave your jeans at home.
  3. The question of sleeves. Sleeves are tricky. Like hem-lines, if you have to ask the question, then err on the side of conservatism. Sleeveless is fine, strapless can be questionable.
  4. The question of sunglasses. I am a big proponent of sunglasses at outdoor weddings – you know you’re going to be sitting quietly for anywhere from 30 minutes to two hours, facing forward, eyes on the bride-and-groom. Wear sunglasses. Parties, however, are a different animal – you’re going to be interacting with people, talking, meeting new people, and sunglasses create a barrier between you and others. It’s flippant, it’s dismissive, it’s just damn impolite. Trade them in for a dashing hat with a brim if you’re concerned about glare.
  5. Shoe choices. Just wear flats. Just do it. No one wants to you aerate their lawn with your stilettos, and even if you’re not on lawn, it’s likely to be stone or pavement, which is just as hazardous in heels. If you simply must wear a heel, keep it to a kitten height. Do not wear flip-flops, no matter how cute they are or how adorable you think the giant daisy glued into them is. If they’re in danger of getting dirty (like canvas shoes), keep the color dark – there will certainly be dirt and grass stains. Men can wear loafers.
  6. Layers. Even in the hottest of climates, it can get cold when the sun goes down. There’s nothing worse than wearing an adorable flouncy blouse and then realizing at 8:00pm that you’re sporting neon high-beams – bring a cardigan or a tailored jacked.

Being Invited on a Boat

I’m on a boat and / it’s goin fast and / I got a nautical-themed Pashmina afghan. – The Lonely Island, “I’m on a Boat”

There are a varied and sundry list of reasons you might be on a boat. Maybe your class reunion is being held on a boat (*shudder*), in which case, wear what you’d wear if it was being held anywhere else + sensible shoes. Maybe your office Christmas party is being held on a boat (*double-shudder*), in which case, see my previous suggestion.

But if you’ve been invited out to a yacht social, a yacht party, or just on your friend’s boat for the day – any time where the idea is to actually spend time on a boat – then you’ll want to behave and dress accordingly.

  1. Shoes. Regardless of the reasons for your being on said boat, wear sensible shoes. If this is actually someone’s boat (as opposed to a ship rented out for a function like a reunion), you’re going to want to wear white, rubber soles, so you don’t scuff the deck. Discard the heels – don’t even try it. Not only is it disrespectful to the deck, but it’s a recipe for disaster: you will look like a land-legged, stumbling moron.
  2. Layers. Layers go for any time you’ll be outside, exposed to the elements. Not only can it get chilly once the sun sets, but weather can always change quickly. Bring a sweater, cardigan, or jacket that you can put on and take off when the temperature changes.
  3. Nautical styles. Red, white, and blue; stripes and solids. Do you have to stick to these styles? You do not, but they are easy suggestions. You can wear whatever as long as it’s ladylike, comfortable, and not a safety hazard concerning the rigging. (No long flowy skirts or complicated dresses here.) Be sensible. And remember: even if it is nautical-themed, that doesn’t mean it’s nautical-appropriate – there are a ton of tiny sailor dresses and four-inch cork platforms out there that should never see the ocean.
  4. Pay attention to the specifics. There are different levels and functions of being on a boat – if you’re going on a riverboat to gamble the afternoon away, the dress code is a little more lax. If you’re on someone’s yacht, however, they may have a “no open-toed shoes” request (for your safety!), or the suggestion that you wear/not wear a bathing suit because there will/will not be swimming. When in doubt, call the hostess or the captain and just be frank about your boat inexperience – people with specific types of knowledge usually like to share it (especially boat owners), and they’ll let you know what’s appropriate and what’s not.
  5. Don’t wear or bring anything you absolutely can’t part with. Now is not the time for Grandma Sophie’s four carat diamond cluster ring or your $700 Hermes scarf – anything you lose on a boat is never coming back. (Besides, do you really want to be that woman screaming to turn the boat around because you knocked your Prada handbag off into the Atlantic? You do not.)
  6. Hair. Appropriate boat-hair is much like appropriate beach-hair: you need to come to terms with the fact that it will not be your best hair ever, and make peace with that. The boat caveat is this: your hair can not be all over the place. Try a french braid, try a twist or a bun, but keep it off your face and away from things and people. Not only does it suck to eat a mouthful of someone else’s hair at high speeds, but it equally sucks to have some bimbo accidentally yanked overboard because she decided this would be her day for Cher-worthy hair.
  7. Behavior, traditions, and customs. Want to know a little bit more about what to expect? The always-charming and painfully honest K. Cooper Ray over at SocialPrimer.com has a tidy little article on Yacht Party Rules.

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  1. […] Expand your wardrobe reasonably (don’t spend money you don’t have), but optimistically – there’s nothing worse than getting invited somewhere, like onto someone’s boat, and realizing you have nothing appropriate to wear. (Been invited to a ladies luncheon, a garden party, or an equally stressful function? Peruse my article on “The Four Most Confusing Dress Codes of All Time.”) […]



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