Stylish Outfit Ideas for a Winter Beach Vacation

Hi Ladies, Are you going on vacation after Christmas and need something cute and tropical to wear?

Whether you’re jetting off to Mexico, cruising the Caribbean, or driving down to Florida, I’ve found that Tommy Bahama has some really nice things!

Here are some new beach vacation looks from this relaxed, colorful brand that makes winter travel down south more fun!


Tommy Bahama - black floral maxi dress

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Chic Floral Maxi

I don’t wear maxi dresses much at home but always take one on vacation. They’re perfect for when you want to feel relaxed and comfy, and when they blow in the breeze, you get that great relaxed vacation feel, which is what we’re all after!

This pretty floral maxi feels slightly more sophisticated than the typical Hawaiian punch ones you usually see in bright, loud colors.

I like the simple, elegant because it just slips over your head. I also think those artsy-looking, oversized botanicals look very classy on that slimming black background.

Some maxis can admittedly look a little frumpy on gals our age,  but the simplicity of cut, the low-key colors, and the artistry of the high, low hem make this dress feel very modern and chic.

Accessories help, too. See how this straw Fedora instantly adds a youthful look to this outfit. I always love a touch of glam, which is why I picked these beautiful sandals with gold discs. A few more accessories and you’ve got a very chic look


green top Tommy Bahama

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Relaxed Tops

I’m giving top marks to Tommy Bahama this season for all the fabulous tops they are showing. There’s plenty to choose from, like cotton t-shirts with 3/4 length sleeves ( so hard to find), upscale beachy sweatshirts, and soft, light-textured sweaters like this one above.

When I travel south, it’s always a thrill to leave behind winter’s dark, cold, hard colors and slip into something light and pastel-like. This mint green hooded top is a beauty. (It also comes in 3 other colors)

You need something like this for breezy days or evenings when a sleeveless tank top or blouse will not do. I love pairing this nubby chenille top with white jeans for an eye-catching vacation look.


blue sundresses for winter beach vacation


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Perky Sundresses

Yay for sundresses! Step out of those heavy jeans into something like this to keep cool and get a little sun on your legs.

I love blue because it reminds me of the ocean and looks light and fresh, worn with white and natural woven accessories. These sundresses are both very cute. It’s hard to choose. Both are a bit flirty, but not too bold. Wear them with cute white sandals, and have lunch by the pool!


black one piece bathing suit Tommy Bahama

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Sexy Swimwear

I don’t think any of us are trying to look like a sex kitten at the beach, but no one wants to come across like a frumpy old lady, either!

This swimsuit is a nice choice. It’s classic, modern, and alluring with that interesting cinched tortoiseshell clip neckline.

Do you see the ruching across the belly? This is fabulous – something I always look for in a swimsuit because it does wonders to camouflage a midlife jelly belly!

Like a bit of color? – Throw on a colorful coverup. Anything goes with chic black.



green cargo pants with crochet top

Cool Cargos

Pants are a must when I go on vacation. I usually take at least one pair of white jeans/pants, but having a second pair is nice. I thought these classy, cropped, wide-leg cargo pants would be great to pack.

These types of pants naturally go with neutrals, but that doesn’t have to mean a boring utilitarian look. Try pairing them with something off-white and textured, like this pretty crochet tank. The feminine look and feel of this tank top balances out the masculine military think of the pants. The result is a modern adventurer kind of look.

Add a slouchy straw bag, rope-like gold bracelets, and fun sandals; you’ve got an upscale-looking, casual, warm-weather look.


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Blue ikat print dress

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Breezy Ikat Print Dress

This gorgeous Ikat midi dress looks as comfy as it is pretty and makes me want to jump on that boat and sail away! It’s always good to pack one dressy that feels a bit dressier for special dinners or events. It would be very easy to dress this one up or down! Try layering on a jacket or playing around with different belts.

Are you ready to hop on the plane? I am! What will you be wearing on your warm-weather winter vacation?

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