It all started when I was browsing through jewelry on Shopbop yesterday. I spotted these earrings (below left), by Giles & Brother: Simple silver studs in the shape of a ship’s steering wheel. Next, I found two more intriguing takes on the nautical charm jewelry trend, courtesy of Rachel Leigh’s necklace and a sea-worthy bracelet by Thea Grant.

 

Giles & Brother studs
 
 My appetite for nautical fashion sufficiently whetted, I went on to find the following cute items from Urban Outfitters
 

 
I’m loving how cute yet simple all of these pieces are, from the little sailboat studs to the authentic-looking cotton rope bracelet (it shrinks to your wrist when you get it wet!) and the adorable, slightly high-waisted sailor pants adorned with buttons at the hips. There were also cute tote bags, perfect for a jaunt on your yacht…or at least a trip to your local swimmin’ hole:
 

 
Which do I love more, the kicky blue and white anchor print, or the striped drawstring bag with the rope handle?!
 
 

J. Crew offers their take on feminine sailor fashion with this cute and comfy-looking navy and white striped shirt dress, at left, and you can put together an easy and affordable little sailor ensemble courtesy of Forever 21 in a nanosecond (striped shirt with ship’s steering wheel applique + worn-in denim capris = summer!). And when it starts to cool down a little? 

 

 
Throw on one of these sweater jackets from the Gap (L) or J. Crew (R). I love the double-breasted cut and the big buttons on both. They’re like little lightweight pea coats!
 
Tips for Rocking the Nautical Look:
  1. Keep the basics in mind: Stripes. Buttons. Navy, red and white. Anything printed with anchors, ships, ships’ steering wheels, etc.
  2. Keep it simple. One or two strong nautical accents at a time, please. For instance: If you’re going to carry that anchor-print tote, perhaps save the charm bracelet for another day. You don’t want to cross over into costume territory.
  3. Keep it flat (your shoes, that is). Sailor looks are tailor-made for simple summer flats! How can you walk the plank in 4-inch heels? Har, har.
  4. Keep it natural. Your hair and makeup should be easy and understated: Clean skin, a touch of mascara, voila. At most, you could get away with a sheer lip stain, but resist the urge to get all done up! It just doesn’t mesh well with the sailor look.
  5. Unless you’re actually going sailing and need one to keep the sun out of your eyes, avoid the bucket hat! Too Gilligan.