Day Sailor

Day Sailin'

Summer is here!  And with the start of warm weather comes invitations to outdoor functions – beach parties, barbeques and other outings.  Most are pretty casual and it’s easy to put your self together and head out.  Just throw on something cute, grab your bikini and go.

But every once in awhile comes one of those casual but not-really-totally-casual events that demand you bring on your fashion A game.  You know the ones – the boss has invited everyone over for a pool party or the firm’s new partner is hosting a “casual” cocktail party at his beach house or you are heading out for a day sail with business associates on a snazzy boat.  This is still casual, and will in some cases even require a bathing suit – EEK!!! – but it is decidedly NOT run of the mill, wear your oversize university tee, casual.  Moreover, these tend to be the events where you want to feel totally confident and totally fabulous. So, what to wear???

Evening get-togethers are fairly easy to attend looking super chic and appropriate.  It’s as simple as taking one great maxi dress in a sumptuous jersey (I find something amazing from Rachel Pally nearly every season) add a statement necklace or earrings, a bold bracelet, a great pair of sandals and you are good to go. Do consider the terrain you will be on – if you expect the event will be on sand or grass I highly recommend wearing a pair of platform espadrilles that aren’t too high and make sure your dress is easy to move in so that you negotiate uneven surfaces with grace.  Also consider the audience – you may want to keep the plunging necklines, strapless or thigh high slits for other times. 

Things get a bit more complicated when you add water.  Pool or beach side, and even in some cases boats, may require swimwear.  No matter how great your body is, you will really want to think about who will be at the party before you pack that new string bikini.  I would always recommend erring on the side of caution and stick with a one-piece or a two piece with really good coverage.  Especially if the party includes people who pay you or potential in-laws – unless, of course, you know them well, or the boss is married to a Kim Kardashian-esque trophy wife.  Make sure whatever swimwear you choose fits well, is not transparent when it gets wet, and is not prone to wardrobe malfunctions of any kind.  The last thing you want is your top departing when you dive in with your co-workers. 

For poolside you can add a cute cover-up dress or pull on a maxi skirt or pants over your suit.  If you plan on being there through the evening don’t forget some sort of light weight wrap or at least bring clothes that can be worn without your suit.  Sitting in a damp swimsuit as the evening cools is not going to be fun….brrrrrr.    

As for boating, well as a boat owner this one is near and dear to my heart.  Having had a few guests aboard in totally inappropriate clothes getting cold, getting wet, not being able to get around on deck, or getting painfully sunburned; I always try to make suggestions to my guests beforehand.  Boating can be a great opportunity for elegant socializing, but whether you get involved in the actual sailing or not, even just getting around on deck is pretty active.  So practicality is a must – skirts, maxi dresses and palazzo pants are only going to work if all you plan on doing is being carefully handed aboard, and then sitting decorously.   

First and foremost, to win the approbation of every captain – wear appropriate footwear – deck shoes, tennis shoes, or flat sandals with non-marking soles.  Polishing black scuff marks off of fiberglass is no fun.  Also, unless you are very comfortable walking onboard, I would steer clear of flip flops, slides or any other footwear that isn’t securely fastened to your foot.  I have been boating my entire life and I am still too clumsy to trust myself not to lose a slide overboard when I go from dock to deck.  Speaking of securely fastened, this is another place where a one-piece suit with fully functional straps is a good idea, as are a hat that doesn’t blow away (I love close-fitting baseball caps) and either lanyards for your sunglasses or bring along a pair you can afford to lose. 

Okay, now that the boring stuff is out of the way you *can* look super cute and chic.  For boating I love an All-American vibe so I scouted out the best of J Crew for this outfit.  First off, a pair of shorts with a fun sailor button detail – not too short or with too low a waist.  With that I added a tunic tee in a nautical stripe but with some funky embellishment to keep it fresh (I leave the anchor embellished, star-bedecked red white and blue looks for the really cute older ladies I see at the marina).  You can layer these pieces on/off with the swimsuit through the day – I chose this one piece in a bright red to add a pop of color, note the substantial straps (you bend over a lot on a boat, trust me).  As it gets cooler I always throw on my beloved cashmere hoodie – it doesn’t feel as damp as cotton, is wonderfully cozy but doesn’t get too hot – PERFECT!  And then I found yet another pair of awesome Sperry Topsiders – these have fun mesh side panels, still good deck shoes, but super cute too. Add a snappy tote bag big enough to hold your sunscreen, your extra layers, and a small cross body bag for shore-side scouting and you are ready to roll. 

So, with a little planning you will still be casual, just really posh casual.  And you will be one of THOSE women you see at these events, you know the ones – perfectly dressed in a way that makes trudging through sand, stepping across docks, and batting beach balls look fun and yet elegant all at the same time. 

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