Reader Mail: What to Wear to a Sailing Event in Mid-May?

what to wear sailingToday’s reader mail has us totally stumped… readers, please weigh in:

I now have my own professional wardrobe crisis – what does one wear to a corporate sailing event? It is in New England, in mid May so will still be chilly. And they have specifically mentioned we must have boat shoes – sneakers or sandals are forbidden. I’m a manager in my early 40’s, what do I wear to look stylish and professional but appropriately sporty? Can I go with some nice golfwear? Help!

Why must companies choose these inevitably awkward events?  This is the kind of event that seems destined to make the one person there who knows about sailing look like a genius, and everyone else either clumsy and uncoordinated (if you try to help and have no idea how) or lazy and entitled (if you try to just enjoy the sail).  Le sigh.  Thoreau once said to beware of all enterprises that required new clothes; we might amend that for companies that they should beware of all enterprises that require new shoes.  The best advice we can offer you is to call the marina or port and find out what you should wear, exactly. (Pictured: Sailing just off Manatee Public Beach, originally uploaded to Flickr by larry_ami.)

4Now that we’ve hedged, we’ll offer a few observations.  A bit of Googling led us to Nautical Boutique, which does sell ladies’ boating shoes, such as a red crinkle patent.  Zappos also sells Sperry shoes, such as the Sperry Top-Sider – Marina Moc 1-Eye (Black Patent) – Footwear, at right (on sale for $89).  We’re not entirely sure what about this makes it a “boating shoe,” but we will note the similarity to Geox’s very comfortable ballet flats, which you could certainly wear again; you may also want to check out some of the more stylish Crocs.

Apparently, the bottom layer of your outfit should not be cotton — but rather something that wicks moisture away from your body but is still breathable.  Brands like Coolmax and Under Armour will be your friends here; if your golfing stuff is a similar fabric then you’re set — otherwise, check out your local sporting goods store.  We would look for a black t-shirt that fits well (not huge) and looks like something normal; we’d accessorize with two layers:  a cardigan and a stylish raincoat, as well as a brightly colored scarf (both to keep you warm and to look vaguely chic and French).  In terms of your bottoms — L.L. Bean sells skirts and pants out of a fabric that wicks moisture and offers sun protection; this might be your best bet.  (Check out the capris, for $44.50, or the skirts, for $39.50.)  If you can find it, opt for moisture-wicking undergarments for the day as well.

In terms of your hair, unless it’s Annie Lenox short, expect to pull it back.  We’ve been meaning to do a longer review, but The Clever Clip is truly amazing — it held our long, thick hair up very comfortably during high winds in Miami a few weeks ago — a tight ponytail is another reliable way to get your hair out of your face.  Be sure to bring SPF, sunglasses, and possibly a hat as well.

Ok readers, please weigh in — what should our reader wear?

Further reading:


  1. In terms of shows, I would advise to make sure it is comfortable and won’t slip off easily. Some marinas also prefer shoes with a light coloured sole.

    It will be much, much colder on the boat than it is on the shore, especially if it is windy or you get wet. I agree with Corporette that wearing layers is a good idea. The temperature can vary greatly depending on rapid weather changes and the speed of the boat. Having spares of anything, especially a spare sweater and socks could be useful in case your get wet.

  2. Boat shoes have special treads on the soles that help grip wet surfaces. As cute as the backless red ones are, go for ones that will actually stay on your feet. Do not get Crocs.

  3. What kind of boat is it? Is it a partner’s personal boat, or something being rented? If it’s personal, I would follow up on the shoe issue. Dark-soled shoes are often forbidden because they scuff the boat’s deck. But if it’s a really big boat and/or not someone’s personal boat, then it may be less of a concern. FYI, the red shoes above look OK but the black ones look to have very dark soles — on my uncle’s boat, those would be forbidden. :-)

    One more warning: if it’s a smaller boat with a smaller group of people, be prepared to work. One of the partners at my former firm often invited groups of 6-10 people onto his boat for an afternoon of sailing. BUT the afternoon involved actually helping him sail the boat, so you would be up on the deck catching the sail, etc, etc. Skirts would have posed a serious problem in that case.

    Also — bring Dramamine!!! On one of the sailing excursions with the above-mentioned partner, I was with my husband, another associate, the partner, his son and one more person. The other associate got violently ill and spent much of the time barfing below deck. Even I, who doesn’t get motion sickness, was queasy for a bit when the waters got choppy. And we had no motion sickness meds on board.

  4. OK, wearing boat shoes is important not for style, but for practicality – they keep you from slipping. Just go with the classic Sperry Topsider. They come in all kinds of colors, but a brown version is just the easiest.

    As for clothing, the suggestion for non-cotton bottoms is a good one, but it’s not like you’re going to be really actively sailing since it’s your first time, so you shouldn’t get very wet. I would avoid the raincoat as well. You are good to go in a nice pair of khakis and a preppy sweater since it will be colder, with polo or something underneath. The reader’s golfwear instinct is not too far off. Think the scene in Wedding Crashers where they go sailing. Think J. Crew.

    The great thing about preppy sailing clothes is that it doesn’t really matter your age. As for the hair, yeah, pull it back or wear a headband because it does get quite windy!

  5. Oh and as for the Sperry’s, I should mention that they may give you blisters when you first get them, but just get them wet and let them dry on your feet. It’s what they’re made for!

  6. I agree with k; although I’ve only sailed a few times, boat shoes usually are meant to grip wet surfaces and stay on your feet while wet. They also should remain warm while wet, or ideally be water resistent, which is why boat shoes are usually leather and usually cover your foot nearly completely.
    Bass makes some boat shoes that are more affordable and have light-colored soles – unfortunately, it looks like their website isn’t working, so here is a different link:

  7. I think if they made a point of telling you to wear boat shoes, that probably means they want white soled shoes. (coming from someone who has spent a lot of time sailing). that is the “traditional” definition of a boat shoe. I would go ahead and get white soled shoes b/c that would be the most embarrassing outfit faux pas. Boat shoes can be very cute! I wear them all the time on land :)

  8. The most important quality in a boat shoe is a non-marking sole followed by grip. Any Sperry shoe is going to fall into that category, wedges not withstanding. As the fiancée of a competitive sailor and a lawyer by day I’ve been in this situation. I highly doubt they’ll have you leaning over the rail so “wicking” isn’t as important as comfort & professionalism. My go-to sailing outfit is jCrew chinos, a ribbon belt, a crisp white button down & a cardigan or cable knit sweater over my shoulders in case the temperature drops. The only other must haves are a pair of Sperrys & some croakiez with bouyancy for your sunglasses. Make sure your handbag zips up completely so it doesn’t spill everywhere when it is down below during your sail. Wear your hair up & enjoy!!!

  9. Boat shoes with light colored soles are an absolute must – otherwise, you are pretty much ok with khakis, a polo shirt and a sweater/cardigan. Definitely agree with think preppy/golf/Jcrew. I am a diehard not preppy person, but I would probably do fitted khakis (I can’t do regular khakis, I just can’t), light colored boating shoes with light soles, a black polo shirt and a light-grey cardigan. I wouldn’t do the raincoat just because it’s an ease of movement issue if you are asked to be useful on the boat, and I might swap the black polo for a vneck black tshirt with a scarf, but the polo just might be easier. Some more thoughts: dramamine and advil and suncreen are all a must. Frankly, pack an extra sweater and long sleeved tshirt if you are bringing a tote on board with you.

    And Corporette, re: Why must companies choose these inevitably awkward events? – OMG SO TRUE. I have been to so many of these at this point, and really, some get sillier than others. Le sigh indeed.

  10. Ugh, I’d fake a family emergency. My commitment to work events stops far short of spending money on shoes I will only wear once.

  11. NO skirts on a sailboat. One word – wind.

  12. If you’re not used to sailing I would also recommend going on a full stomach. I’ve been sailing less than 5 times and have found my tendancy towards seasickness is directly proportional to how hungry I am while I’m on the boat. It’s been much more enjoyable when I’ve eaten an actual meal shortly before getting on the boat.

  13. Great clothes ideas, but at the risk of being a little off topic, a few additional non-clothing items I’d bring (my brother used to sail quite a bit):

    Second the Dramamine, absolutely.

    Carry a sunblock stick SPF 35 (like Neutrogena) so that you won’t show up with raccoon tan to the office; reapply often as the wind and reflected sun will do a number on your skin and lips. It doesn’t run the risk of making your hands slick like a liquid might.

    Also if you get cold easily, consider handwarmers like those for skiing, if you’re near a sporting goods shop… they’re easy to keep in your pockets and can be such a source of comfort if you’ll be out in the wind freezing for hours. Scarf is also a great idea and very versatile as it can go from hair to neck to belt easily if you’ve got plans for afterwards.

  14. Delta Sierra :

    V – I’m with you. Certainly sneakers (with rubber, or rubber-ish, soles) would be a good idea for your own safety. But after that, there’s a real rudeness in hosting a ‘social’ event and then getting all dictatorial about what guests can and cannot wear. It puts concerns about boat maintenance before concerns about your guests. It’s like hosting a cocktail party and requiring everyone remove their nice shoes and plop around in fluffy slippers to spare your precious floors. Let’s face it, the boat owner’s first idea here is to save money on having the decks cleaned after the party.

  15. I have no sailing suggestions… but I really want to find out more about this clever clip… does it really work??

  16. NOT CROCS — under any circumstances… EVER. They are stupid and will make you look stupid.

  17. I’m with V – the whole event sounds about as unpleasant as it gets, from the need for “wicking” (read: you will get wet while clothed) fabrics to the preppy look (never my thing unless we’re talking a jcrew sundress) and, most of all, those hideous boat shoes. I’m not one to wear stilettos everywhere, but you’ve got to be some hot chicky to look cute in those. My hat is off to anyone who does, but I’d skip the event at (almost) all costs.

  18. On crocs, I’ve never seen them in person and don’t feel particularly compelled to try, but if you wore something like this would people really scream “CRRRRRRRRROCS” and commence ostracization? They seem fairly innocuous.

  19. Mid-may? It will be COLD. Bring a jacket, preferably one that is windproof. Patagonia or similar would be good. Agreed on the classic boat shoes and khakis on the bottom, but please bring something heavier than a sweater. YOU WILL BE COLD otherwise.

  20. Re: Jen’s question on the clever clip, I haven’t actually tried it, but The Daily Obsession reviewed it a while back:

    I’ve been meaning to get one… I think two recommendations makes it a definite.

  21. Agree with all of the comments regarding light-soled grippy shoes. That’s boat shoes….

    Bring something windproof–rainwear, windstopper polar fleece, and perhaps even a hat (think cute skullcap). It can be really cold. All of your layers can fit in a tote bag. Bring one.

    And to the naysayers, unless you get really seasick almost everyone enjoys sailing. It’s really relaxing to go cruising. And if you have to help, in my experience (even though I know how to sail), boys tend to like to “prove their might” when winching sails, etc. They pretty much shove women out of the way to prove their manliness on sailboats. Must be some weird instinct. I’ve never figured this out, but even complete newbie (boys) shove me out of the way when sailing. So funny!

  22. @v (2:17) – I’m sorry, those crocs may not scream “CROCS” at me but I think the ostracization would commence regardless – they look like those big, old-man orthopedic shoes.

    The “Santa Cruz” style, however, would work for a boat shoe – white sole and simple upper? Not bad for a Crocs price point.

    Wear pants that have a bit of stretch – awkward-height steps and clambering may abound.

  23. Anonymous :

    Don’t wear khaki. If they get wet they are see thru. Wear khaki material but opt for navy. Wear a cute white thick polo w/ a cardigan over it. Bring a windbreaker in case you are sitting where the water comes up. DO NOT under any circumstances wear socks with boat shoes. And seriously, don’t worry so much about how you look. Be the girl that is there having fun, not constantly fixing her hair.

    Oh and the poster about crocs probably didn’t mean the ugly gardening shoes but rather their new line of professional and sports stuff.

  24. I asked the original question and a big THANK YOU to everyone who is replying and for Corporette herself who was nice enough to address this. I have been in panic mode ever since the stupid invite came out.

    Of course this is a Male-run event. And it is a certain level of management, it would be career ending for me to miss this. So I’m stuck. And I so appreciate all the empathy from all of you! I will be thinking of you when I am on this boat swearing and muttering to myself. Just to make this a bit more tortuous, you should be aware that the sailing is a team building event! So I will have to do something involving directing the boat, although they won’t say what, and they swear it does not require previous sailing experience.

    Anyway thank you, thank you, thank you for all your advice, it never even occured to me to bring sunscreen, dramamine, etc so I’m definitely doing that. And I think I underestimated the coldness factor, your consensus there and with the rest of the wardrobe advice is really helpful. I hope this does actually turn out to be fun. Okay I’m off to buy some boat shoes!!

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