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Vacation Outfits Ideas

Jb and I recently got back from our anniversary trip to Jamaica and we took the kids on our family vacation last week. Eh, I meant trip (vacation with kids, is not a vacation, but a relocation?) Even though we always have a blast, it’s a lot of WORK. Last year I said that family trip may have been one of the most challenging trips with all the kids. We are always on the go and someone always needs something. This year went a little smoother and we decided to not take any technology with us… highly recommend! Aside from all that I had several request for outfits links while on these two summer trips. So I wanted to make sure to round up all my vacation outfits in one place for you to shop whether you are headed on a romantic getaway or family trip, I’ve got you covered. So below you’ll find all my outfits, plus a few tips on WHAT to pack for your next trip!

LEFT PICTURE: one piece / hat / sunglasses
RIGHT PICTURE: top / bottoms

My love for Brasilian brands runs DEEP. I mentioned over on my stories while on vacation that if you have not tried Brasilian swimwear, you are missing out. The quality, how it fits, everything about it is out of the park when compared to American swimwear. I found PH Praia, a Brasilian company now in the US (Miami), and they carry some of the SOFTEST Brasilian swimwear. The unique prints are just ?.


OUTFIT #1: top / bottom / hat / sunglasses
#2: top / bottom / belt

If you don’t want to try Brasilian swimwear, make sure you head to this post, where I tried several different brands and fits that I’m sure you’ll find something! These two above were two of my favorites aside from PH Praia ones from the trip. Both are very different styles, but so cute! The seashell belt too, is the cutest accessory if you’re feeling fancy.

Outfit #1: Swimsuit

Outfit #2: Top // Bottoms



LEFT OUTFIT: one piece / cover-up / sandals / hat
MIDDLE OUTFIT: top / bottom / cover-up (similar)
RIGHT OUTFIT: cover-up / one piece / sandals / hat / sunglasses

My cover-ups the last few years very much have a theme, call me extra, but I LOVED it. Nothing says vacation cover-ups like crochet. I’m SO upset I left my Mumu one at the restaurant in Destin last year and that someone stole it instead of turning it into the lost and found (believe me, I called). I immediately placed a new order and got it in the mail the day after we arrived ? ( I love it that much).




Dress // Clutch // Sandals // Bangles // Earrings

OUTFIT #1: dress (similar) / shoes / earrings
#2: dress (similar) / sandals / earrings / clutch (similar)

When it comes to vacation outfits, I like to pack a lot of dresses and easy pieces to wear. Of course, it’s easier to style and wear dresses, but it’s also easy to pack (that’s my biggest tip)! I didn’t bring any shorts, or denim with me. Just easy, light fabrics to wear. And in the summer, I love to wear bold colors and print, so I usually gravitate to that during summer vacation trips too. I can’t even say I have a favorite look this trip; I loved all the outfits I packed!

OUTFIT #1: top / skirt / shoes / clutch (similar) / earrings
#2: dress (similar) / sandals

Outfit #1: Top // Shorts // Shoes // Purse // Earrings // Bangles

Outfit #2: Top // Shorts // Shoes // Bag

Outfit #1: Top // Bottoms // Bag (similar) // Shoes // Necklace // Earrings // Hat

Outfit #2: Dress // Shoes // Clutch // Earrings


palm earrings / gold bead bangle / all-weather bangles

All-Weather Gold Bangles // Hat // Shoes // Sunglasses // Lip Balm // Sunscreen

Finally, I also try to pack light when it comes to accessories. Neutral pieces, again, I know that match well with different outfits. For example, these TKEES sandals can be worn with anything. This clutch also pairs with any outfit. A straw hat you love can again be worn during the day, or night to cover up the sandy beach hair.

The one thing I will pack more of is jewelry; since they are smaller and lighter, I tend to overdo it there. But only because I think it’s a fun way to dress up your vacation outfits without doing too much. Also, as you can see from all the pictures, I LOVE my all-weather bangles. They are plastic, so you don’t have to worry about swimming in them and they are not loud. I found the dupes to them here (under $10) if you want the look for less! You can also use code UPTOWNWITHELLYBROWN to save 10% off your entire purchase at check out.

Thank you so much for stopping by, I hope you enjoyed my round-up of vacation outfits, and I hope you found some looks and even items you love for your next vacation!

Have a good one!


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