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Vacation Inspiration: 4 Looks Inspired by Key West


Key West Beach

A few weeks ago, I went on a small vacation to Key West, Florida. Although I had visited before, this time I found myself completely inspired by everything around me, from the laid-back, eclectic residents to my gorgeous surroundings.

That’s why I decided to share my vacation experience with you: My hope is that you’ll also be inspired by this small Florida island and perhaps motivated to find fashion inspiration on your next vacation. In order to get the creative juices flowing, here are 4 outfits inspired by the sights, history and atmosphere of Key West:

1. Sunset Celebration at Mallory Square

Mallory Square Sunset

Mallory Square is an area located right on the waterfront of historic downtown Key West. Every night, residents and tourists alike gather to watch the sun sink into the Gulf of Mexico. However, people often arrive two hours before the sun goes down, because every evening Mallory Square turns into a mecca for musicians, street performers and artists, creating a fun and unique atmosphere for watching a beautiful sunset.

Key West Outfit 1

Product Information: Skirt, Top, Bracelet, Bag, Flats

For this first outfit, I wanted to create a look inspired by the colors of a sunset, which are captured in the gradient pattern of this skirt. When paired with a slouchy tee, the two pieces make a cute yet casual outfit for a warm summer night. Comfortable flats in a bright color are perfect for walking around all night long, while the matching woven bracelet adds some interest. Finally, add a simple drawstring bag for a sleek look.

2. Duval Street

Duval Street

Duval Street is the main drag in Key West and the place for shopping, interesting attractions and amazing restaurants. There’s always something going on here, and once it gets dark, this is the place to go for nightlife as well. There’s tons of unique bars and dives in Key West, which are definitely worth checking out if you’re over 21.

Key West Outfit 2

Product Information: Top, Shorts, Necklace, Bag, Sunglasses, Sandals

For the Duval Street-inspired outfit, I created a daytime look that could easily transition for a casual night out. A simple white top and fitted shorts are two basics that can easily be dressed up or down with accessories. A nautical-inspired necklace and fun fringed bag are unique pieces that add interest to the look, while the sunglasses protect your eyes while adding a bright pop of color.

Finally, for footwear, I chose a true Key West favorite– Kino’s. You can actually watch as artisans create these sandals by hand in a shop just off Duval Street. They’re super comfortable, last forever, and are really inexpensive–perfect for college girls on a budget!

3. The Hemingway House

Hemingway House

Of course Key West isn’t all about beautiful sunsets, interesting bars and great shopping– it’s also a town full of rich history. Countless artists, musicians and authors have called Key West home over the years. One of the most well-known residents was author Ernest Hemingway, who lived there for most of the 1930s.

You can visit his gorgeous Key West home (seen above) today, which is on a huge lot filled with gorgeous, winding gardens. Hemingway’s house is also home to dozens of cats, (did you spot the one drinking out of the fountain in the photo above?) which are decedents of Hemingway’s original 6-toed cat. These are some of the friendliest felines I’ve ever met, so if you’re a cat person, this place is for you!

Key West Outfit 3

Product Information: Dress, Necklace, Bag, Bobby Pins, Oxfords

The interior of the home is filled with lots of wordly treasures and interesting photos of Hemingway’s travels, which is why I chose this dress– it reminds me of something you would wear on a safari, but still speaks to the home’s breezy, casual feel. The menswear-inspired oxfords and green messenger bag both have a 1930s feel with a modern touch, while the cat necklace is an adorable nod to all the felines that call the Hemingway House home. Finally, I added some simple bobby pins that mimic the lush foliage that surrounds the house.

4. Hemingway’s Writing Studio

Hemingway Writing Studio

Since I was so inspired by the Hemingway house, I wanted to create one more look, this time using Hemingway’s writing studio as inspiration. The room is located above an old carriage house on the property, and Hemingway wrote For Whom the Bell Tolls, as well as three other novels and numerous short stories in this room.

For the last look, I wanted to create an outfit for all the amazing guys that read CF (we know you’re out there!), or just for the girls who want to pass a tip along to their boyfriend, guy friend or other fashion-conscious male their lives. For this look, I was inspired by Hemingway himself, as well as the masculine feel of his writing studio.

Key West Outfit 4

Product Information: Chinos, Henley, Fedora, Watch, Sperry’s

At the base of the outfit are some casual chinos and a comfortable henley, which are both lightweight enough to wear on a warm summer day. Some classic Sperry’s mimic the rich tones of Hemingway’s writing desk, while the wrap-around watch adds a vintage touch. If you’re one of those guys that wears a baseball cap 24/7, why not switch it up with a straw fedora? The hat adds an element of cool that looks straight out of the 1930s.

So, what do you think?

Have you ever felt inspired by a vacation? Have you ever visited Key West? What do you think of these outfits? Be sure to leave a comment and let me know your thoughts!

Posted on on August 8, 2010 / Filed Under: Inspiration / Tags: , , , , , ,

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18 Responses to “Vacation Inspiration: 4 Looks Inspired by Key West”

  1. 1
    August 8th, 2010 at 8:26 am

    Ooh, this might be one of my most favorite posts of all time! I adore Key West. I went there on a family trip when I was younger and we visited all the places you list here. The atmosphere there is unreal – amazing! Bravo for including a guys outfit, too, it’s so chic.

  2. 2
    August 8th, 2010 at 9:41 am

    I love this post! I went to Key West a couple of weeks ago and it was so much fun. All these outfits fit a vacation to KW perfectly! (And I love that you included the Kino’s Sandals… I am obsessed with them!)

  3. 3
    August 8th, 2010 at 9:47 am

    How fun! Hemingway writes some depressing stuff, so who knew his house was so cheerful?! Love the cats. This article is awesome, but why no Key Limes??
    Key West is definitely going on my Future Adventure List…And now I’ll know what to wear. :)

  4. 4
    August 8th, 2010 at 9:52 am

    this is such a clever idea!! i love the idea of taking a bit of culture home with you from the places you visit!

  5. 5
    August 8th, 2010 at 10:02 am

    I LOVE this! I visited Key West this past June for the first time since I was a little kid and absolutely adored it. I came back relaxed, tan and with three pair of Kino’s (Including the ones in look 2)!

  6. 6
    August 8th, 2010 at 10:05 am

    I absolutely love every outfit you featured in this article. I’ve visited Key West in the past, and can imagine wearing each of these outfits there. Darn, this is making me crave the Blond Giraffe’s key lime pie on a stick!

  7. 7
    August 8th, 2010 at 10:10 am

    This was such an amazing post! I loved all of the outfits. I really want to go there and see Hemingway’s house- it looks so interesting.

  8. 8
    August 8th, 2010 at 10:35 am

    Love these looks! I esp love the kino’s!!!!!!!!!


  9. 9
    August 8th, 2010 at 12:09 pm

    You should do one on St. Augustine!

  10. 10
    August 8th, 2010 at 12:33 pm

    i’ve never been, but these outfits are REALLY well put together! i love it!

  11. 11
    August 8th, 2010 at 3:00 pm

    Now I have to visit Key West! It looks totally awesome. Earnest Hemingway is the big man on campus, he rocks!

  12. 12
    August 8th, 2010 at 3:45 pm

    This so awesome!! Ashley, your posts are always some of my favorites. I haven’t been to Key West in ages, but this makes me want to go back so badly!!! The outfits capture the initial inspiration perfectly! Oh, and I second Paula’s suggestion. Great post :)

  13. 13
    August 8th, 2010 at 6:25 pm

    Such a great idea! I was just in Key West a few months ago (and actually used to live there!)… I wish I had seen this post though, it definitely would’ve inspired me to dress a little better :)

  14. 14
    August 8th, 2010 at 7:47 pm

    I have visited Hemingway’s house several times in the past and have since always considered it just about my favorite place in the universe. Love the veranda that wraps around the entire house!! Your pieces work together beautifully, thanks for the post!!

  15. 15
    August 8th, 2010 at 9:40 pm

    I LOVE these outfits! I wish i had them on vacation! I especially like the dress in the last outfit..I think i’m going to order it. I’ve never been to the Hemingway House, but i think its definitely worth a trip.

  16. 16
    August 28th, 2010 at 9:17 pm

    Key West is one of my favorite places to visit. My family lives in Florida and every so often we hit up Key West for a quick vacation. It’s our home away from home. Everything about it is so calming and perfect. I wanna go right now=(

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