IF YOU’RE PLANNING A KEY WEST TRIP SOON AND WONDERING WHAT YOU ACTUALLY NEED TO PACK, THIS IS EVERYTHING I BROUGHT, WHAT I ENDED UP WEARING THE MOST, AND A FEW THINGS I WAS VERY GLAD I HAD WITH ME!
KEY WEST IS DEFINITELY ONE OF THOSE PLACES WHERE YOU WANT TO PACK CUTE OUTFITS, BUT YOU ALSO HAVE TO REMEMBER IT’S HOT, HUMID, SUNNY, AND VERY WALKABLE. COMFORT MATTERS JUST AS MUCH AS THE AESTHETIC HERE.
BETWEEN RESORT DAYS, COFFEE RUNS, DUVAL STREET NIGHTS, AND SUNSET WALKS, HERE’S EVERYTHING I’D RECOMMEND BRINGING FOR YOUR KEY WEST GETAWAY!
RESORT & POOL DAY ESSENTIALS
Most of our trip was spent either by the pool, walking near the beach, or exploring around the resort, so lightweight pieces were an absolute must!
I lived in:
breezy dresses
linen pieces
matching sets
swimsuits with oversized button downs
flowy skirts
lightweight tanks
Trust me… Key West heat is no joke! The more breathable your outfits are, the happier you’ll be.
I’d also highly recommend packing:
multiple swimsuits
a beach tote
sunglasses
a cute cover up
lots of SPF
a hat for walking around during the day
The sun there is STRONG!
NIGHTS OUT ON DUVAL STREET
At night, Key West is super casual but still fun to dress up for. I definitely overthought outfits before the trip and quickly realized nobody is wearing anything super fancy. Most people are in sundresses, sandals, matching sets, or casual vacation outfits.
Go to outfits for the best night out:
lightweight dresses
sandals you can actually walk in
cute tops with flowy skirts or shorts
small crossbody bags
minimal jewelry because of the heat
Comfort is key because you’ll end up walking way more than expected.
SHOES I WAS SO GLAD I PACKED
This might be the biggest thing I’d stress for Key West… bring comfortable shoes.
The island is incredibly walkable and between Duval Street, restaurants, resort exploring, and sunset spots, we were constantly on our feet.
The shoes I reached for most were:
white sneakers
comfy sandals
flat slip-ons
I would honestly skip heels completely unless you know you’ll only be sitting at dinner.
MY BEACH BAG ESSENTIALS
A good beach tote ended up being one of my most used things during the trip.
I always kept:
sunscreen
lip balm
sunglasses
portable charger
water bottle
hair clip
mini makeup bag
camera
A portable charger is an absolute MUST because between maps, photos, restaurant searches, and being out exploring all day, your phone battery disappears FAST.
THINGS YOU CAN LEAVE AT HOME
A few things I packed that I barely touched:
heels
heavy makeup
denim
jackets
complicated outfits
The vibe in Key West is very relaxed and effortless. The simpler the outfit, the better.
MY BIGGEST PACKING TIP FOR KEY WEST
Pack for comfort first and cute second! The best outfits ended up being the easiest ones to throw on after a pool day or before walking to dinner. Key West has such a laid-back island energy and honestly that’s part of what makes it so fun.
You really don’t need over the top outfits to fit in there. A cute sundress, sandals, salty beach hair, and a frozen drink in hand is basically the Key West dress code!
🩵 ✨ 🌺 🐚
This Key West packing list is definitely coming with me on every future trip back because honestly… there were a few things I was SO glad I packed and a few things I definitely didn’t need at all. Hopefully this helps make planning your own Key West getaway a little easier so you can spend less time stressing over outfits and more time enjoying the island.
Be sure to follow along for more Key West blogs, resort stays, travel guides, outfit inspiration, and all my favorite little finds from the trip!
- Travels By Dawn
GET ALL YOUR KEY WEST OUTFITS!
FAQ | WHAT SHOULD I PACK FOR A KEY WEST VACATION?
When packing for a Key West vacation, the biggest thing to focus on is lightweight and breathable clothing. Key West is hot, humid, sunny, and extremely walkable, so comfortable outfits are essential. I’d recommend packing sundresses, swimsuits, sandals, linen pieces, matching sets, sunglasses, SPF, and lightweight tops you can easily rewear throughout the trip.
FAQ | WHAT SHOULD I WEAR IN KEY WEST?
The overall Key West style is very relaxed, tropical, and casual. Most people wear breezy vacation outfits like sundresses, sandals, linen shorts, tank tops, and flowy skirts. Even at night on Duval Street, the vibe stays pretty laid back, so you definitely don’t need overly fancy outfits.
FAQ | WHAT SHOES SHOULD I BRING TO KEY WEST?
Comfortable shoes are probably the MOST important thing to pack for Key West. Since the island is so walkable, I wore sneakers, flat sandals, and slip-ons the entire trip. Between walking Duval Street, exploring local restaurants, and spending time near the waterfront, comfortable shoes make such a difference.
FAQ | HOW MANY OUTFITS SHOULD I PACK FOR KEY WEST?
I’d honestly recommend packing more lightweight outfits than you think you’ll need. Because of the heat and humidity, I ended up changing outfits more often than expected after walking around during the day. Extra tank tops, swimsuits, casual daytime outfits, and easy vacation dresses definitely came in handy.
FAQ | IS KEY WEST CASUAL OR DRESSY?
Key West is definitely more casual than dressy. Even the nightlife on Duval Street feels relaxed and effortless compared to bigger cities. Most people are wearing sundresses, sandals, tropical prints, matching sets, and easy vacation outfits rather than heels or formal clothing.
FAQ | WHAT SHOULD I NOT OVERPACK FOR KEY WEST?
I’d skip heavy fabrics, jackets, uncomfortable shoes, and overly complicated outfits. Key West has a very effortless island vibe, so simple lightweight pieces end up working best for almost every part of the trip.
FAQ | WHAT BAG SHOULD I BRING TO KEY WEST?
A beach tote and a small crossbody bag were definitely my most used bags during the trip. The tote was perfect for pool and beach days, while the crossbody made walking around Duval Street and exploring Key West at night super easy.
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