28 VACATION OUTFIT IDEAS FOR YOUR WINTER TRIP!

It’s hard not to fantasize about getting away when the skies turn gray and the temps start to dip below 40. Part of the planning (and dreaming) fun is thinking of your stylish winter vacations outfits. You’ve got a lot to consider, more than just your personal style. It’s about fitting that style into the atmosphere and environment of your destination. Functionality is a huge issue, too. What you’ll pack to sit by the pool is different than what you’ll pack for skiing.

We’ve put together perfect vacation looks based on our dream getaways (whether we will get away is another story), inspired by the spirit of the trip and potential location.

Winter Travel Packing List! For sun or snow we have you covered. From trendy to cozy, traditional to classic, and chic to edgy – get out of your travel fashion rut with these fashion clothes for the winter.

 

*Click on the links Below the images to buy online NOW!

 

For a Resort Getaway

 

Look#1

Winter Vacations Styles 28

Shop the Look:

1. Valentino Tropical Dream Brocade Sleeveless Dress, Black/Multi, $6,650.00Free Shipping + Free Returns

2. Dolce & Gabbana Small Straw Flower Top-Handle Crossbody Bag, Multi, $3,395.00Free Shipping + Free Returns

3. Gucci Pilar Blind for Love Espadrille Flat, Black/Multi, $650.00. Free Shipping + Free Returns

 

Look#2

Winter Vacations Styles 27

Shop the Look:

1. Karla Colletto La Dolce Vita Off-the-Shoulder One-Piece Swimsuit, $288.00. Free Shipping + Free Returns

2. Natura Bisse C+C Oil-Free MacroAntioxidant Sun Protection SPF 30, 1.0 oz., $62.00. Free Shipping + Free Returns

3. Ray-Ban Round Mirrored Sunglasses, $185.00. Free Shipping + Free Returns

4. Balenciaga Bistro Panier Small Straw Tote Bag, Natural/Red, $945.00. Free Shipping + Free Returns

5. Joie Nice Knotted T-Strap Sandal, Platinum, $125.00. Free Shipping + Free Returns

 

Related:

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Look#3

Winter Vacations Styles 26

Shop the Look:

1. Mara Hoffman Waves Tie-Front Coverup Pants, $265.00Free Shipping + Free Returns

2. Mara Hoffman Waves Tassel Sarong, Dusty Rose, $100.00. Free Shipping + Free Returns

3. Mara Hoffman Waves Wrap-Front Swim Top, $125.00. Free Shipping + Free Returns

Mara Hoffman Waves Low-Rise Hipster Swim Bottom, $110.00. Free Shipping + Free Returns

4. Sophie Hulme Cromwell Mini Tote Bag, Rainbow, $695.00. Free Shipping + Free Returns

5. Valentino Rockstud Double Butterfly Espadrille Flat, Denim, $945.00.. Free Shipping + Free Returns

 

Look#4

Winter Vacations Styles 2

Shop the Look:

1. Emilio Pucci Parasol Silk Maxi Coverup Skirt, Rosa/Arancio/Limo, $1,040.00. Free Shipping + Free Returns

2. Emilio Pucci Parasol Printed String Bikini Set, Rosa/Arancio, $395.00. Free Shipping + Free Returns

3. Devon Leigh Turquoise Chain-Link Statement Earrings, $450.00. Free Shipping + Free Returns

4. Chloe Suede Sandal with Colorful Fringe, Reef Shell, Original: $1,190.00, NOW: $797.00, Extra 25% Off : $597.75. Free Shipping + Free Returns

 

Related:

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Look#5

Winter Vacations Styles 25

Shop the Look:

1. Johanna Ortiz Bahama Striped Floral-Shoulder Jumpsuit, Blue/Pink/White, $2,150.00. Free Shipping + Free Returns

2. Henry Beguelin Mina Medium Rumble-Wash Satchel Bag, White, $1,395.00. Free Shipping + Free Returns

3. Tabitha Simmons Lassie Crisscross Flat Slide Sandal, Champagne, $545.00. Free Shipping + Free Returns

 

Look#6

Winter Vacations Styles 24

Shop the Look:

1. Altuzarra Harry Sleeveless Lace Dress, Provence Blue/Red, $1,795.00Free Shipping + Free Returns

2. Fendi Dotcom Medium Hypnotic Satchel Bag, Multi,, $3,450.00. Free Shipping + Free Returns

3. Balenciaga Studded Caged Flat Slide Sandal, Bleu Profound, $635.00. Free Shipping + Free Returns

 

Look#7

Winter Vacations Styles 23

Shop the Look:

1. Missoni Mare Chevron Fringe-Hem Poncho Coverup, $850.00. Free Shipping + Free Returns

2. Akola Gray Druzy & Horn Beaded Bracelet, Original: $150.00, NOW: $112.00, Extra 25% Off : $84.00. Free Shipping + Free Returns

3. Fresh Sugar Sport Treatment Sunscreen SPF 30, $25.00. Free Shipping + Free Returns

4. Rene Caovilla Beaded Lace-Up 45mm Sandal, Orange/Multi, $975.00. Free Shipping + Free Returns

 

Related:

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Look#8

Winter Vacations Styles 22

Shop the Look:

1. Fendi Illusion Wavy-Cutout Peasant-Sleeve Blouse, Cobalt, $1,600.00Free Shipping + Free Returns

2. Fendi Striped Tie-Waist Wide-Leg Pants, Blue/Multi, $1,700.00. Free Shipping + Free Returns

3. Lizzie Fortunato Suede Collage Beaded Necklace, Red, Original: $290.00, NOW: $232.00, Extra 25% Off : $174.00. Free Shipping + Free Returns

4. Gianvito Rossi Strappy Suede 105mm Sandal, Multi, $845.00. Free Shipping + Free Returns

 

Look#9

Winter Vacations Styles 21

Shop the Look:

1. Stella McCartney Sleeveless Smocked Lace Gown, Natural, $2,615.00.. Free Shipping + Free Returns

2. Chloe Faye Medium Perforated-Pineapple Shoulder Bag, Abstract White, $2,290.00. Free Shipping + Free Returns

3. Gianvito Rossi Satin Crisscross Fringe Slide Sandal, 645.00. Free Shipping + Free Returns

 

Look#10

Winter Vacations Styles 20

Shop the Look:

1. Missoni Crewneck Sleeveless Knit Midi Dress, Red/Multi, $1,865.00Free Shipping + Free Returns

2. Nanette Lepore Pretty Tough Goddess Printed One-Piece Swimsuit, $160.00. Free Shipping + Free Returns

3. Ashley Pittman Taaluma Set of Two Bracelets, $295.00. Free Shipping + Free Returns

4. Bottega Veneta Medium Flow Wave Intrecciato Tote Bag, $3,500.00. Free Shipping + Free Returns

5. Giuseppe Zanotti Strappy Suede 110mm Sandal, Blush, $1,150.00. Free Shipping + Free Returns

 

Related:

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Look#11

Winter Vacations Styles 5

Shop the Look:

1. Fuzzi Lace-Print Mosaic One-Shoulder Maxi Dress, $395.00. Free Shipping + Free Returns

2. Norma Kamali Mio Floral-Print One-Shoulder Swimsuit, $200.00. Free Shipping + Free Returns

3. TOM FORD Anoushka Streaked Cat-Eye Sunglasses, Gray/Peach, $445.00Free Shipping + Free Returns

4. Saint Laurent Monogram Blogger Crossbody Bag, Beige, $995.00. Free Shipping + Free Returns

5. Stuart Weitzman Romanflat Suede Flat Gladiator Sandal, Amaretto, $445.00. Free Shipping + Free Returns

 

Look#12

Winter Vacations Styles 1

Shop the Look:

1. Dolce & Gabbana Embellished Long Peasant Gown, Pink Print/Multi, $8,295.00. Free Shipping + Free Returns

2. Trina Turk Ibiza Bandeau One-Piece Swimsuit, $148.00. Free Shipping + Free Returns

3. Lana Nude Fringe Earrings in 14K Yellow Gold, $2,170.00. Free Shipping + Free Returns

4. Givenchy Geometric Butterfly Sunglasses, $295.00. Free Shipping + Free Returns

5. Gucci Barbette Knotted Espadrille Wedge Sandal, Gold, $1,100.00. Free Shipping + Free Returns

 

Look#13

Winter Vacations Styles 7

Shop the Look:

1. Missoni MareZigzag Beach Coverup Dress, Multicolor, $695.00. Free Shipping + Free Returns

2. Dior Diorama Caged Mirrored Sunglasses, Pink, $475.00. Free Shipping + Free Returns

3. Gianvito Rossi Lola Flat Frayed Denim Sandal, Blue, $695.00. Free Shipping + Free Returns

 

Related:

NEED CUTE WINTER OUTFITS? HERE’S 5 WEARABLE WAYS OF STYLISH LAYERING!

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Look#14

Winter Vacations Styles 6

Shop the Look:

1. Valentino Lace Off-the-Shoulder Mini Dress, Metallic Red, $3,380.00Free Shipping + Free Returns

2. Oscar de la Renta Impatiens Flower Drop Earrings, $425.00. Free Shipping + Free Returns

3. Aquazzura Wild Thing Suede Flat Slide Sandal, Red, $475.00. Free Shipping + Free Returns

 

Look#15

Winter Vacations Styles 19

Shop the Look:

1. Oscar de la Renta Pleated Floral-Print Halter Gown, White/Multi, $3,490.00. Free Shipping + Free Returns

2. Oscar de la Renta Long Beaded Tassel Clip-On Earrings, $395.00. Free Shipping + Free Returns

3. Balenciaga Navy Cabas Medium Leather Tote Bag, Red, $1,455.00. Free Shipping + Free Returns

4. Gianvito Rossi Strappy Suede 105mm Sandal, Multi, $845.00. Free Shipping + Free Returns

 

Look#16

Winter Vacations Styles 18

Shop the Look:

1. Johanna Ortiz La Santa Maria Ruffled Floral Gown, White, $3,550.00. Free Shipping + Free Returns

2. Dior So Real Mirrored Iridescent Sunglasses, $620.00.. Free Shipping + Free Returns

3. THE ROW Market Suede Braided Tote Bag, Saddle, $1,890.00Free Shipping + Free Returns

4. Stuart Weitzman Elixir Braided Leather Wedge Sandal, Adobe, Original: $455.00, NOW: $318.00, Extra 25% Off : $238.50. Free Shipping + Free Returns

 

Related:

HOW TO WEAR WINTER FLORALS!

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Look#17

Winter Vacations Styles 17

Shop the Look:

1. Chloe Pintucked Pineapple Eyelet Tunic, White, $1,995.00.. Free Shipping + Free Returns

2. NEST Jewelry Blue Jasper Cluster Necklace, $395.00. Free Shipping + Free Returns

3. Nancy Gonzalez Daisy Medium Japan Landscape Crocodile Satchel Bag, Black, $4,350.00Free Shipping + Free Returns

4. Gucci Carolina Braided-Rope Wedge Sandal, Black/Red, $595.00. Free Shipping + Free Returns

 

 

Planning Winter Getaway?

 

Look#1

Winter Vacations Styles 16

Shop the Look:

1. Nobis Abby Knee-Length Coat with Fur Hood, $995.00Free Shipping + Free Returns

2. Brunello Cucinelli Monili Spinner Wheeled Carryon Suitcase, Gray Pattern, $12,995.00. Free Shipping + Free Returns

3. Burberry Harbor Fur-Cuff Harness Boot, Black, $650.00. Free Shipping + Free Returns

 

Look#2

Winter Vacations Styles 15

Shop the Look:

1. Sofia Cashmere Fur-Trim Cashmere Poncho, Black, $900.00. Free Shipping + Free Returns

2. Versace Monochromatic Pavé Aviator Sunglasses, Black, $490.00. Free Shipping + Free Returns

3. Alexander Wang Rex Rabbit Fur Mini Satchel Bag, White/Gray, $895.00. Free Shipping + Free Returns

4. Frye Jen Shearling Ankle Boot, Smoke, $398.00. Free Shipping + Free Returns

 

Related:

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Look#3

Winter Vacations Styles 14

Shop the Look:

1. Fabio Gavazzi Cashmere-Belt Sable Vest, $18,500.00. Free Shipping + Free Returns

2. Mario Portolano Lambskin Mink-Fur Cuffs, $415.00. Free Shipping + Free Returns

3. La Canadienne Phebe Suede Chunky-Heel Knee Boot, Stone, $495.00. Free Shipping + Free Returns

4. Saint Laurent Cassandre Small Tassel Crossbody Bag, Black, $1,890.00. Free Shipping + Free Returns

 

Look#4

Winter Vacations Styles 13

Shop the Look:

1. Joie Haesel C Speckled Cashmere Poncho, Heather Cacao, $498.00Free Shipping + Free Returns

2. MICHELE Cape Golden Chronograph Watch w/Silicone Strap, Green, $445.00.. Free Shipping + Free Returns

3. UGG Classic Heritage Toscana Gloves, Chocolate, $160.00Free Shipping + Free Returns

4. Pedro Garcia Xadani Shearling Chunky-Heel Bootie, Silt Brown, Original: $650.00, NOW: $455.00, Extra 25% Off : $341.25. Free Shipping + Free Returns

 

Related:

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Look#5

Winter Vacations Styles 12

Shop the Look:

1. Moncler Aphrotiti Shiny Quilted Down Coat w/Fur Hood, $1,895.00Free Shipping + Free Returns

2. Anya Hindmarch Shearling Fur Ghost Crossbody Bag, Black, $1,595.00. Free Shipping + Free Returns

3. UGG Ava Exposed-Fur Knee Boot, Black, $275.00. Free Shipping + Free Returns

 

Look#6

Winter Vacations Styles 11

Shop the Look:

1. J. Mendel Colorblock Horizontal-Mink Fur Coat, Black/Garnet/Mahogany, $29,000.00. Free Shipping + Free Returns

2. Elizabeth and James Cynnie Micro Shearling Fur Crossbody Bag, Black, $325.00. Free Shipping + Free Returns

3. Stuart Weitzman Lowland Suede Over-The-Knee Boot, $798.00. Free Shipping + Free Returns

 

Look#7

Winter Vacations Styles 10

Shop the Look:

1. THE ROW Sua Draped Open Cardigan, $950.00Free Shipping + Free Returns

2. Balenciaga Blackout City AJ Shoulder Bag, $2,950.00. Free Shipping + Free Returns

3. Stuart Weitzman Grandiose Suede Pointed-Toe Bootie, Topo, $525.00. Free Shipping + Free Returns

 

Related:

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Look#8

Winter Vacations Styles 9

Shop the Look:

1. Canada Goose Lorette Fur-Hood Down Parka, $950.00. Free Shipping + Free Returns

2. David Yurman Albion Stud Earrings with Diamonds and 18k Gold, $1,400.00. Free Shipping + Free Returns

3. THE ROW Happy Hour 7 Mink Shoulder Bag, Berry Red, $1,590.00. Free Shipping + Free Returns

4.  Christian Louboutin Who Dances Button 85mm Red Sole Bootie, Black, $1,495.00. Free Shipping + Free Returns

 

Look#9

Winter Vacations Styles 8

Shop the Look:

1. Derek Lam 10 Crosby Fur-Trimmed Hooded High-Low Hem Parka, Loden, $895.00. Free Shipping + Free Returns

2. Shinola 34mm Birdy Moon Phase Watch with Leather Strap, Brown/White, $575.00. Free Shipping + Free Returns

3. Chloe Marcie Suede Satchel Bag, Caramel, $2,350.00. Free Shipping + Free Returns

4. Stuart Weitzman Gofurit Mink-Trim Ankle Boot, Brown, $875.00. Free Shipping + Free Returns

 

Related:

A NEW LOOK AT YOUR CONTEMPORARY WARDROBE ESSENTIALS!

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Look#10

Winter Vacations Styles 3

Shop the Look:

1. Chloe Horizontal-Striped Silk Poncho, Blue/Rust, $1,350.00.. Free Shipping + Free Returns

2. Chloe Silk Turtleneck Top w/Slit Bell Sleeves, Ivory, $795.00. Free Shipping + Free Returns

3. TOM FORD Aaron Trimmed Aviator Sunglasses, $380.00. Free Shipping + Free Returns

4. Saint Laurent Cassandre Small Tassel Crossbody Bag, Black, $1,890.00. Free Shipping + Free Returns

5. Stuart Weitzman Midland Suede Over-the-Knee Boot, $875.00. Free Shipping + Free Returns

 

Look#11

Winter Vacations Styles 4

Shop the Look:

1. Bogner Short Hooded Down Coat w/ Fur Trim, Off White, $1,117.00. Free Shipping + Free Returns

2. Les Petits Joueurs Mini Alex Woven-Leather Bunny Bag, Black/Red/White, Original: $1,150.00, NOW: $862.00, Extra 25% Off : $646.50. Free Shipping + Free Returns

3. Devon Leigh Crystal Teardrop Double-Hoop Earrings, $195.00. Free Shipping + Free Returns

4. Moncler Laetitia Fur Lace-Up Boot, Beige, $835.00. Free Shipping + Free Returns

 

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Hope you enjoyed our vacation outfit ideas for your winter trip.

If you want more inspirations and ideas, check out our last year’s articles on gift ideas for her.

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