3 Ways to Wear a Sailor Dress Without Looking Like You’re Going to a Costume Party

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I saw this Gabriella Rocha Sailor Dress and I wasn’t sure if it was part of the new Halloween costume arrivals or not. Okay, it’s not as over-the-top as some other dresses we have seen, but does it look costume-y to you?

Gabriella Rocha Sailor Dress in Black/Grey and Red/BlackGabriella Rocha Sailor Dress in Black/Grey and Red/Black, $65.00

If your answer is yes, then well, you’re not alone in thinking that. I initially mistook it for a costume too. But then I thought that this dress could have the potential to be pretty, especially when styled with some top fall 2010 trends.

Read on to find out how to make the Gabriella Rocha sailor dress not only wearable but so cute that its fashion style blog-worthy. Check out these 3 cute ways to wear a sailor dress:

1. Casual Prep

How fitting is it that the English prep trend came right when classes started?

Look like you’re ready for school with a cropped schoolboy blazer, a brown leather satchel and a pair of black opaque tights, but still, show ’em that you know how to have fun with menswear oxfords – in 4 1/4″-high wedge heels:

Look like you're ready for school with a cropped schoolboy blazer, a brown leather satchel and a pair of black opaque tights

  1. Sanctuary Schoolboy Blazer, $148.00
  2. Kate Spade New York Solid Opaque Black Tights, $28.00
  3. Lucky Brand Back in the Saddle, $149.00
  4. Twelfth St. by Cynthia Vincent Kole Oxford Wedges, $325.00

2. Military-Minded

Since the military trend is so hot right now, pulling off this look is so easy that it almost feels like cheating. If you’re up for a bigger challenge, try a jacket with faux fur trimming and some military boots in an over-the-knee height:

BB Dakota Manderson Leather Jacket and Sam Edelman Dixie Over The Knee BootsBB Dakota Manderson Leather Jacket; Sam Edelman Dixie Over The Knee Boots

3. Feminine Pretty

Make like Blair Waldorf and girly up everything you’re wearing with light pastel colors, soft fabrics, and of course, sparkly jewels. Throw on a dainty majorette jacket, put on a plush beret, and as for the required jeweled ballet flats, the color is your choice:

How to wear a sailor dress like Blair Waldorf

  1. Free People WTF Majorette Jacket, $148.00
  2. Haute Hippie Deluxe Thigh High Socks, $95.00
  3. Juicy Couture Reversible Knit Beret Hat, $48.00
  4. Report Fernley Ballet Flats, $69.95

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