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Edited by on May 26 2011 at 3:49 PM

Fleet Week has officially dropped anchor in New York, meaning that from now until May 30th the city’s streets will be flowing with seamen.  To bag your very own sailor, here are 5 Navy-inspired ensembles that will put some wind in his sails.

Hey Sailor: 5 Naughty Nautical Looks to Get Your Fleet Week Flirt On

Look 1Slutty Preppy:

From the Ivy League to 20,000 Leagues.

Hey Sailor: 5 Naughty Nautical Looks to Get Your Fleet Week Flirt On

 

 

Hey Sailor: 5 Naughty Nautical Looks to Get Your Fleet Week Flirt On

Sweater cardigan
$80 - generalpants.com.au

 

Hey Sailor: 5 Naughty Nautical Looks to Get Your Fleet Week Flirt On

Betsey johnson
$250 - betseyjohnson.com

 

Hey Sailor: 5 Naughty Nautical Looks to Get Your Fleet Week Flirt On

Giuseppe zanotti boot
530 GBP - selfridges.com

 

Hey Sailor: 5 Naughty Nautical Looks to Get Your Fleet Week Flirt On

TopShop print handbag
$152 - topshop.com

 

Hey Sailor: 5 Naughty Nautical Looks to Get Your Fleet Week Flirt On

 

Look 2Chic Week:

An officer and a gentlewoman.

Hey Sailor: 5 Naughty Nautical Looks to Get Your Fleet Week Flirt On

Hey Sailor: 5 Naughty Nautical Looks to Get Your Fleet Week Flirt On

Sheath dress
$795 - barneys.com

 

Hey Sailor: 5 Naughty Nautical Looks to Get Your Fleet Week Flirt On

Alexon ivory bolero jacket
99 GBP - debenhams.com

 

Hey Sailor: 5 Naughty Nautical Looks to Get Your Fleet Week Flirt On

 

Hey Sailor: 5 Naughty Nautical Looks to Get Your Fleet Week Flirt On

Judith Leiber gold handbag
$4,830 - net-a-porter.com

 

Hey Sailor: 5 Naughty Nautical Looks to Get Your Fleet Week Flirt On

Miriam Haskell pearl flower necklace
$1,400 - charmandchain.com

 

Look 3Funny Girl:

People who need sailors are the horniest people in the world.

Hey Sailor: 5 Naughty Nautical Looks to Get Your Fleet Week Flirt On

Hey Sailor: 5 Naughty Nautical Looks to Get Your Fleet Week Flirt On

Sonia by Sonia Rykiel sailor dress
$495 - net-a-porter.com

 

Hey Sailor: 5 Naughty Nautical Looks to Get Your Fleet Week Flirt On

Anna Sui microfiber tight
$14 - zappos.com

 

Hey Sailor: 5 Naughty Nautical Looks to Get Your Fleet Week Flirt On

Miu Miu platform heels
$445 - net-a-porter.com

 

Hey Sailor: 5 Naughty Nautical Looks to Get Your Fleet Week Flirt On

Shoulder bag
539 EUR - styleserver.de

 

Hey Sailor: 5 Naughty Nautical Looks to Get Your Fleet Week Flirt On

Pedre bangle bracelet
$105 - endless.com

 

Look 4Shore Thing:

Bling it out Jersey style for some sailor smoosh time.

Hey Sailor: 5 Naughty Nautical Looks to Get Your Fleet Week Flirt On

Hey Sailor: 5 Naughty Nautical Looks to Get Your Fleet Week Flirt On

Tommy Hilfiger tie front top
100 GBP - houseoffraser.co.uk

 

Hey Sailor: 5 Naughty Nautical Looks to Get Your Fleet Week Flirt On

TopShop animal print top
$20 - topshop.com

 

Hey Sailor: 5 Naughty Nautical Looks to Get Your Fleet Week Flirt On

Milly cotton short short
159 EUR - stylebop.com

 

Hey Sailor: 5 Naughty Nautical Looks to Get Your Fleet Week Flirt On

Alexander mcqueen heels
$1,028 - bluefly.com

 

Hey Sailor: 5 Naughty Nautical Looks to Get Your Fleet Week Flirt On

Kate Spade clutch bag
$225 - zappos.com

 

Hey Sailor: 5 Naughty Nautical Looks to Get Your Fleet Week Flirt On

By Malene Birger shell jewelry
$170 - 25park.com

 

Hey Sailor: 5 Naughty Nautical Looks to Get Your Fleet Week Flirt On

Missoni turban hat
98 EUR - jades24.com

 

Look 5Boys Just Want to Have Fun:

Don’t ask, do tell for the boy hoping to get his deck swabbed.

Hey Sailor: 5 Naughty Nautical Looks to Get Your Fleet Week Flirt On

 

Hey Sailor: 5 Naughty Nautical Looks to Get Your Fleet Week Flirt On

 

Hey Sailor: 5 Naughty Nautical Looks to Get Your Fleet Week Flirt On

PRADA LINEA ROSSA Sailor pump
$358 - farfetch.com

 

Hey Sailor: 5 Naughty Nautical Looks to Get Your Fleet Week Flirt On

ROBERT GELLER Linen dock hat
$350 - farfetch.com

 

Hey Sailor: 5 Naughty Nautical Looks to Get Your Fleet Week Flirt On

las jewelry fish ring
$108 - oaknyc.com

 

Hey Sailor: 5 Naughty Nautical Looks to Get Your Fleet Week Flirt On

Wavy Stripes Tank
$13 - forever21.com

 

Hey Sailor: 5 Naughty Nautical Looks to Get Your Fleet Week Flirt On

NAVy Anchor Motif Chino Shorts – Mens Shorts – Clothing – TOPMAN
topman.com

Now that you’ve got some style pointers, just make sure you wear your wetsuit when you go diving for love during Fleet Week. Scurvy might be a thing of the past, but a high seas romance can leave you scraping barnacles off your hull for the next few months.

 

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Story by Lester Brathwaite

I was center square from 1969 to 1978, during which I perfected the art of the zing as well as a crippling cocaine addiction. Bea Arthur was responsible for both. @LesFabian lester dot brathwaite at gmail

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