See Hatsie Travel / See Hatsie Wear

Wear: My Key West Suitcase

Key West Packing

By now you should be adequately convinced that Key West Florida is a destination that should be on your Travel list.  It’s full of great food, there are plenty of things to do for any type of traveler, and the weather seriously can’t be beat.  It was beautiful every single day.  

It was hard for me to put together a packing list for this trip.  Being smack in the middle of Winter in the Northeast, it’s difficult to imagine a land where the weather isn’t even a little bit cold in January, even at night.  I was also pretty set on not buying anything new for the trip, aside from a solid “key west color” outfit for our family pictures and a new swimsuit, as I avoided them like the plague last Summer.  Using what I had, I packed free-flowing breezy tops, shorts, and a couple of pairs of pants.  Open toed flats and comfortable walking shoes were a must.  Most of the things I brought could easily be worn for day or night, as neither were really fancy in Key West.  Even “fancy” restaurants are decidedly casual.

Here’s what was actually in my suitcase.  The things I couldn’t find exact matches for, I found something similar that is currently for sale.  I tried to pack light, and I definitely could have gone lighter, but even so, I think this could get you started when you’re planning your trip to paradise!


Key West Packing Shirts


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I didn’t pack hardly any dresses–in fact I only packed one for New Year’s Eve.  If I had done a lot of shopping prior to the trip, I probably would have tried to find some cute and tropical maxi dresses, but as I said, I tried to use what I had (which was plenty.  I need to pare down, not buy more!)

Because of this, I packed mostly separates that could be dressed up or dressed down or worn with pants or shorts.  I brought a couple of t-shirts, some flowy tops, and a couple of button ups that could be worn a few ways.  I know black doesn’t seem like the most “island” color, but I wear a lot of black in real life and so I wear a lot of black in vacation life too.

On any given day, we could be walking around, participating in some sort of water activity, and then enjoying a dinner out, so a change of clothes were necessary.  I probably could have made do with a few less tops, but I will say I wore each of these at least once.


Key West Packing Bottoms


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I showed up in Key West wearing Jeans, sneakers, and a short-sleeved T-Shirt.  Within 30 minutes I was so hot and sticky I was miserable and severely needed a dip in a pool.  I knew right away I was so glad I packed the shorts that I did; pants were simply too hot to wear during the day.  During the day, I lived in either swimwear or one of three pairs of shorts I brought, mixed with any of the tops above.  I wore pants some nights, mainly those white jeans, but those olive chinos were light and comfortable as well.

Each of these choices were appropriately casual–I mean it when I say that even on New Year’s Eve, most everyone was in shorts and sandals.


Key West Packing Accessories


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I brought a couple of lightweight scarves mostly for travel days, but also for hanging around the house, which we kept really cool.  I brought my favorite “vintage” yankees hat for walking around and hanging by the pool.  I also brought jewelry, but I feel like jewels are pretty personal, so you bring what you think you’ll wear!


Key West Packing Shoes


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I lived in sandals, especially since we were walking pretty much everywhere.  I was glad I brought those sneakers too, especially on days when we walked far, like when K and I explored the Key West Cemetery.  I brought a pair of heels for night-time, but only wore them once or twice.  I embraced the open-toed, flat-heeled freedom at all times of the day.

Those gold ones are really comfortable and were great for daytime outfits, and those jeweled sandals spruced up an otherwise casual night time outfit.  You can’t go wrong with leopard, ever, anywhere.


Key West Packing Swim


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Our condo had a pool area which we all loved.  Mostly I wore a suit and my white cover-up with sandals if I was staying in, and if we were heading out I’d throw on a button up and some shorts over my swimsuit so I’d be dressed but could easily transition into beach wear if needed.

My mom bought me a monogrammed fishing shirt for our fishing excursion, because a trip is nothing if it doesn’t include the appropriate costume.  Turns out, it’s now one of my favorite cover ups–those fishermen know what they’re doing.

New Year’s Eve




I packed my favorite and most comfortable cotton black maxi dress.  It was perfect for New Year’s Eve–it looked polished and dressed-up but still casual and comfortable.  It was the only dress I brought, but really it’s because I didn’t want to go buy something just for this trip.  My sister in law wore comfortable and casual dresses all week and she was adorable.

Other things I packed included:

  • Loungewear/work out wear
  • Toiletries and hair styling tools
  • Jewelry

And that’s about it.  It all fit into one large roller-board suitcase, and it was only a couple of pounds overweight (but that’s because on the way there I packed a really special bottle of wine that I had been saving to drink with my mom and sister in law).  As I said, I probably could have pared this list down even more, although once I was there I was glad for the options, especially since it was 23 degrees when I left New York, and I couldn’t even fathom what 78 degrees and sunny felt like.  (Spoiler alert, it feels like heaven.  Pure heaven).

Our week in Key West was so beautiful and restful and exciting and fun.  I loved every minute of it and even though we were there a full week, I absolutely could have stayed longer.  I hope that you and yours take a trip there soon.  I also hope that you take me with you!  I’m a fun travel partner, promise.  I hope you enjoyed Key West Week.  I sure did!

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