This is the time of year when a lot of people make like migrating birds and head south for the winter. If a much-needed tropical getaway is in your horizon, check out a few of our picks below for resort-ready style.

Now you’re ready to set sail to the land of sunshine and relaxation!

1. LAUREN Ralph Lauren Tie Dye Stripe Tubini, 2. Havaianas Slim Flip Flops in Fuchsia, 3. Nanette Lepore Hula Gal Tropical Wrap Dress, 4. Max and Cleo Camille Floral Print Shirt Dress, 5. Lilly Pulitzer Peachie Bandeau and Surf's Up bikini bottom, 6. Ella Moss Portofino Cover Up Hooded Tunic, 7.Brighton Flamingo Tote, 8. Goorin Brothers Macey Floppy Hat, 9. Stuart Weitzman Sanjuan

Since my team and I are off to Costa Rica once again for our Spring 2012 style shoots, I thought it was only fitting to start off the year’s first Style Destination post with where else—Costa Rica!

With its lush, green landscape and gorgeous coastline, Costa Rica is definitely a tropical playground. Being comfy and cool is top priority when packing for any tropical destination. Here are a few of my essentials for this trip:

1. Goorin Brothers Malibu Hat: Humidity and hair just don’t mix. This lightweight fedora is a must for easy, fuss-free hair!

2. Reef Butter 3 Flip Flops: I love how cushy and comfy these sandals are! They’re perfect for walking along the beach or sightseeing around town.

3. Ella Moss Rhapsody Cover Up Hooded Poncho: A sheer coverup is perfect for throwing on while you enjoy a little poolside cocktail!

4. The North Face Women’s Horizon Tempest Pant: A pair of lightweight and breathable roll-up pants is perfect for those sudden downpours.

5. Oakley Dispatch II Polarized: These oversized shades keep the glare away while looking totally glam.

6. Keen Whisper Sandals: We do a ton of walking around in different terrain during our shoots, and these durable waterproof sandals are a lifesaver.

7. Gabriella Rocha Alika Bikini Set: An adjustable bikini doubles as a great layering piece underneath those slinky tank tops and summer dresses. I like to bring a few during my trips!

Women: 1. Sprit Hoods Forest Fox, 2. Echo Design MSoft Ruched Echo Touch Gloves, 3. Prana Tassel Beanie, 4. Prana Dela Pocket Scarf

Men: 1. Echo Design Marled Neck Warmer, 2. Prana Murphy Beanie, 3. Goorin Brothers 20 Guage Hat, 4. Fossil Trent Colorblock Convertible Gloves

Kids: 1.Levi's Kids Buff Check Convertible Gloves, 2. Neff Yo Gabba Gabba "Plex" Beanie, 3. Nike Kids Stripe Beanie & Mitten Set, 4. Roxy Kids Glacier Texting Gloves, 5. Roxy Kids Arctic Scarf, 6.San Diego Hat Company Sock Monkey Beanie

Give the gift of stylish warmth this holiday season with some of the coolest winter accessories around. From cozy knit scarves for him and her, to colorful beanies for the little ones, give them a reason to want to brave the winter cold with these perfect accessories all wrapped up underneath the tree!

We’re seeing a slew of lush and luxurious velvet popping up everywhere this season! Whether it’s with jeans or accessories, adding a dose of velvet to your fall ensembles lends fabulous texture and richness to both evening and daytime looks.

Check out a few of our current faves:

1. Free People Rose Velvet Bustier: We love this underneath semi-sheer blouses or low-cut top to add a bit of “vintage boudoir” style. 

2. Matt & Nat Hendrix Convertible Clutch: Edgy meets luxe with this utterly chic handbag.

3. Vans Viral Skinny Belt: Cinch in your sweater dresses with a pop of rich velvet!

4. Goorin Brothers One Shoe Cloche Hat: Wear this retro-inspired hat with your favorite tweed coats for an ode to the glam ‘20s.

5. James Jeans Twiggy Velveteen: There’s something so positively opulent and upscale about these ravishing velvet skinnies.

6. Cole Haan Morgan Ballet Slipper: Too fabulous to just wear in the house, these plush flats are the epitome of understated luxury.

7. Vince Camuto Single-Breasted Walker Coat: Touches of velvet do wonders in giving this classic coat a distinguished flair.

Howe PJ Tech Cotton Blazer, Obey Revolution Nubby Tank, Obey Recon Cargo Shorts, Steve Madden Lande sneakers, Goorin Brothers Hammond, Ray-Ban New Wayfarer

He’s ahead of the curve, trend-savvy and not afraid to take style risks. The Trendster is always on the lookout for the coolest style pieces and coming up with interesting ways to wear them.

Our stylists put this particular Trendster outfit with fresh urban style in mind. The fashion-forward combo of a blazer, graphic tank and camo shorts are punctuated with sleek high top sneakers. Throwing on a cool fedora and classic Wayfarers rounds out this neo-urban look perfectly.

To see even more outfits for your specific style, check out our new and improved Shop by Personality page.

Modern city slickers.  

Left: Ben Sherman Cardigan, Calvin Klein V-neck tee, Calvin Klein Jeans Army Herringbone Modern Chino, Converse Chuck Taylor All Star Slim Ox, Fossil Monroe belt

Right: Fred Perry Gingham Shirt, 7 for All Mankind Slimmy Slim Straight-leg Jeans,Lacoste Osier 2 oxfords, Fred Perry Twin Tipped tie, Goorin Brothers Bad Boy fedora

Casual city dressing is a study in subtleties and refinement. The modern city slicker is all about merging classic looks with modern simplicity. There’s no reason why you can’t rock a pair of blue jeans or khakis to the hottest restaurant uptown. Just make sure you stick to understated classics that exude effortless style.