Right now the weather is starting to make the steady transition from refreshingly chilly to brutally cold. These plummeting temperatures can also lead to a sharp decline in your motivation to put your best fashion face forward and looking cute may soon take a back seat to being comfortable.

Fortunately, you can escape this proverbial style rut by upgrading your wardrobe with a few key pieces that are both functional and fashionable. Keeping your look fun and fresh even when the weather becomes increasingly heinous is definitely one way to bring some light into the long, dark winter days.

The best strategy to freshen things up is to focus on items that will fit into your existing wardrobe seamlessly and help you get more mileage out of those old standbys by providing new ways to wear them.

To help you on your way, we’ve rounded up the top five items worth investing in for effortlessly fabulous, winter-ready ensembles.

1. Poncho

Ponchos emerged as one of the prevailing trends from the Fall/Winter 2011 runways, and frankly, what's not to love? They're comfortable, practical and provide a fresh alternative to your standard pea coat. While they were once considered a staple for only the Bohemian sect, today's ponchos appeal to a much wider audience with a range of styles to choose from: classic American prepster, edgy fashionista, pared down minimalist. Whatever you consider your personal style to be, there’s a poncho out there with your name on it.

Aside from the trend-factor, ponchos are also really practical pieces as we transition from fall to winter. Wear it on top of a tee or tank while the weather is still warmish and then take advantage of its roomy shape when we sink below coldish by wearing it over heavy layers.

Splurge: Missoni Fringe Poncho, $235 

Savel: Gianni Bini Penny Poncho Sweater, $88

2. Duster Coat

A coat is probably the most worthy cold weather investment since it will basically be your outfit for three months—at least, when you're outdoors (or if you work in a freezing office). This season, the hottest trend in outerwear was, by far, the duster coat. There is just something so romantic and glamorous about this floor-sweeping style that renders it thoroughly irresistible. It is also incredibly figure friendly, creating a long, lean, statuesque-like silhouette.

In addition to helping you look thin and beyond fashionable, the extra long length of this will also go the extra mile in keeping you nice and warm--literally from head to toe--when the weather turns especially ruthless.

 (Super) Splurge: L.A.M.B Laser Cut Boil Wool Maxi Coat, $650   

 Save: Anne Klein Long Hooded Coat, $179

3. Maxi Skirt

Coats aren't the only things going to great lengths this season; skirts are also getting in on the fun! The maxi skirt trend has been going strong for a few seasons and continues to get better and better, with new variations of this old standby continuously cropping up to keep things interesting. While this season’s resurgence of the slit up-to-there maxi is definitely tempting, sticking to a more basic version is a more practical choice that will help you get more mileage out of this fantastic staple.

Maxi skirts can be tricky to wear, so be mindful of the proportions of the rest of your layers. If the skirt is flowy, team it with structure pieces on top, like a tailored blazer or fitted sweater. If the skirt is more streamlined, you can either keep the rest of your look body-con or experiment with looser layers and contrasting textures and shapes. To keep from looking (or feeling) frumpy, finish the look with a pair of comfortable wedges. A bit of extra height makes everything all right!

If you don’t want to take it to the max, a midi skirt (one that hits mid-calf) is another way to go long. This style literally exploded on the runways this season so you can be sure to find plenty of options lining the racks. Just be mindful how you wear your midi, lest you wind up looking like a schoolmarm.

Splurge: Vince Maxi Skirt, $245 

Save: American Apparel Interlock Long Skirt, $42 

4. Bright Pants

Pants came in all shapes this season: tapered, flared, skinny, high-waisted--there was no shortage of great silhouettes to choose from to suit your style and figure. The one thing all these fabulous styles had in common was that they came in a bevy of bold and bright shades, marigold, cobalt, fuchsia, emerald—suffice to say Roy G. Biv was well represented this season!

Bright pants definitely make an exciting alternative to your basic black or grey trousers and are a surefire way to stand out from the crowd, but in a good way! You can take your look to the next level by wearing bright-colored layers on top for some color-blocking fun or keep things simple by tempering your bright bottoms with neutrals on top. Stepping slightly outside your comfort zone can be exciting; just don’t go too far over the line, which can be anxiety-inducing!

Splurge: Dolce Vita Jenny Wide Leg Pants, $220

 Save: ASOS Premium Straight Leg Pants, $62

5. Flat Over the Knee Boots

A high-quality pair of classic "OTK" boots is definitely an investment worth making. They make the perfect finishing touch to just about any outfit by adding a shot of polish and sleek sophistication. While they’ve been making the rounds for a few seasons now, there’s still something a bit unexpected about them, which keeps this shoe trend fresh and continuously cutting-edge.

Flat OTKs are best if you want more bang for your buck. In addition to the comfort factor, they’re much more practical and daytime-appropriate, unlike heeled styled which can sometimes seem more working girl than woman going to work. If you’re craving an extra lift, a style with a slight wedge will do the trick without compromising your comfort level.

Splurge: Adrienne Vittadini Shoes, Mac Convertible Over the Knee Boots, $249

Save: Chinese Laundry Night Owl Boots, $99