What to Wear on Your Winter Vacation

Headed on a trip this holiday season? You book the flights, we have your outfits covered. Sharing 10 head-to-toe styled looks that can take you from The Bahamas to Big Sky, and everywhere in between.

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If you are planning a trip out west, then you already know that cowboy boots are a necessity. Pair them with a metallic pant and an elevated plaid jacket to make a fashion-forward statement.

This outfit puts the après back in ski with a bold metallic jacket and muted burgundy pants. It wouldn’t be ski season without a star piece from perfect moment that is sure to make your trip just that!

While this outfit is Paris perfect, it is begging to be worn all Winter long. The tweed dress paired with the matching mini bag is a fresh fashion choice that is sure to receive “beaucoup de compliments”. My french may be limited, but this outfit isn’t. The neutral undertones make these pieces wearable time and time again!

If you are headed on holiday somewhere as cold as London, this dress is the perfect choice to stay warm, while looking tea-ready. To make the outfit more interesting, pair the dress with a similarly toned jacket (in a different texture) and a bright red clutch.

Being in New York during the holidays is magical, but the stress of looking New York ready isn’t. To stay on trend for the big city, opt for a large fur jacket paired with a slinky, silk dress and tall black boots. Mixing in an animal print bag feels fashion forward and the interesting shape of these earrings from Roxanne Assoulin is the perfect finishing touch. All that’s left is calling a cab!

Heading south for December? Good call! This resort piece from Alice + Olivia’s newest collection is the perfect addition to your beach getaway. It is not only flattering, but the material is easily packable. Pair with pale pink accessories and this amazing on sale bag from Marni!

This time of year there are so many amazing summer pieces on sale like this set from Alemais. It is extremely versatile as you can dress it up for dinner and drinks, or pair it with a bikini as a daytime coverup. Add a pair of sandals from Tkees (my favorite simple sandal brand) that you will wear time and time again.

Cala de la Cruz is quickly becoming the “it” brand for resort-wear. This dress is a new arrival and is already selling quickly thanks to its comfortable material and stunning green pattern. Pairing this dress with a similar geometric shaped necklace makes the outfit look intentionally put together, while the raffia bag gives the look a care-free sense of style.

The Bahamas call for easy dresses that look dressed up with sandals. This one from SIR is breathable and the neckline is universally flattering. Pairing this dress with this denim sun hat adds a fun mix of patterns, while remaining pretty neutral. Keep the accessories simple with these gold studs and just add your SPF!

Red has been the color of the year and swimsuit brands are quickly taking note. This amazing two- toned one piece is the perfect statement to make in Mexico. Layer this coverup over top as it ties just above the rosette detail on the swimsuit. Feeling fun? Tie the whole look together with a red shoe!