1. It has to go with my boots/shoes
Even though you shed your coat once you come in from the cold, outside, your coat is part of your outfit — which is why it’s critical to pick wisely. I have a really diverse collection of shoes: everything from crazy high 5″ Balenciaga platforms, to sunshine-yellow ankle booties, to everyday flat boots, so I try to find a coat that will transition smoothly from high fashion to low-maintenance. I find that leather jackets, peacoats, and belted puffers make the switch most easily.

2. It has to have at least one look-at-me detail
A good coat can last forever so it only makes sense to invest in a new one if there’s something special about it. I look for details that upgrade the coat from cool to drool such as interesting buttons (vintage-looking, colored, toggles, interesting shapes = LOVE); fun prints & patterns (herringbone, houndstooth, striped, plaid, quilted, unusual = HAUTE); or sharp shapes (right now I’m really feeling funnel necks).

3. It has to be WARM
I am (almost) past the stage where I’ll freeze for fashion. I do not play around with NYC winters, so I go for coats that button/zip all the way up the neck (hence, my interest in the funnel neck coat). The coat should also be in a brrr-fighting fabric like wool, cashmere, down, shearling, or fully-lined leather.

What makes a coat worth your investment?

Part of my rationalization for not being more creative is because I know I’m going to put a coat over everything I wear. If that’s the case, why bother trying?

Well, I should bother because there are lots of fantastic (and warm) winter style options.

1. Wear this adorable toggle sweater over a long-sleeved shirt, with skinny jeans, boots and a bright scarf.
2. Most waterproof and practical winter boots are fairly ugly. However, this cute pair from Target has a tie back so you can tighten the top around your jeans (preventing snow from wetting your socks). They also have a subtle wedge heel, which will glam up your outfit a couple notches.
3. This newsboy hat has a Blair Waldorf-like bow on the side.
4. Fingerless gloves are really practical: it’s easier to drive, text and open your chapstick. These have a cool military-inspired look.
5. Shawl-collar cardigans are chic and so comfortable. They look best with a more fitted look on the bottom (either jeans or a pencil skirt, for instance) and really interesting oversized jewelry.
6. If you have the moxie to try out a funky, faux-fur hat, by all means, wear one like this!
7. A traditional holiday sweater like this looks good with more modern pairings. I would try it with dark leggings, flat-soled boots and a great pair of earrings.
8. I would really like to open these Nine West boots on Christmas morning. I can’t lie: I love them.
9. Wear a spin on the traditional Ugg boot style with these cuffed sweater boots.
10. I really like these London Fog boots: they have a little wedge and are fur-lined on the inside.
11. When it comes to scarves, you can’t go wrong with plaid.

What do you like to wear when the weather turns cold?

Oversized button-downs are hardly a new concept, but this season, designers and buyers alike have warmed to the idea.

FASHIONISTAS

Most trendy stores like Urban Outfitters and H&M offer the look as an oversized shirt or a shirt -inspired dress. As an alternative, go the cheaper route and raid the closets of the men in your life.

Finding these pieces should be relatively easy, but it is often difficult to style them. Use the look with a heavy hand, and being one step away from a hot mess is probable. The first issue is length. If you’re going for a dress look, it should fall about half way above your knee. If going for an oversized shirt look, slim/tapered pants or leggings are a necessity and you’re going to want the length to cover a good six inches of your thighs. Imagine you’re wearing a mini-skirt. The length should go down at least that far. You might want to go a tad longer, depending on the fit of the pants and your individual proportions.

The second issue is silhouette. The sheer volume of an oversized shirt often needs to be balanced by cinching the waist with a belt. Take note — retire your thick wide belts. They are not only often overbearing, but have been killed to death! The new belts are skinny and a fresh breath of air. Just take a look at the belt in the first picture.

Let’s talk accessories. If you are beltless or using a belt that blends well with the color of your top, a gold or silver chained necklace is a great addition. Also, bangles would work with mostly any top. Just keep your color palette in check. To finish the look, throw on a pair of heels or wedges. As a special touch, the right full skirt might pack extra punch if worn under the top…just pay close attention to proportion.

FASHIONISTOS

It’s true. Guys often have it easier than girls. If you do not have the money to pay Henrik Vibskov prices, I recommend sizing up one or two sizes. Any flannel will do. It’s that simple. Now here comes the fun part – finishing the look! My number one style tip is balance. If you’re going to do oversized, you’ll need tapered/skinny jeans.

To complete the look, layering is encouraged. The more layers you can accomplish without looking or feeling heavy, the better. An excellent and easy layer example would be to leave the shirt unbuttoned and worn over a tee. On top of the button-down, wear a thin cotton buttoned vest; think sleeveless cardigan. B.Son offers the perfect vest. To top it off, add a scarf in a solid color or subtle pattern. When pairing multiple patterns, pick one bold pattern and one subtle pattern. Link the patterns with a dominant color. For shoes, I recommend a pair of TOMS or Converse.

Statement accessories:

Metallic flashes (that aren’t over-the-top) like this skirt by Abaete:

And all the pretty dresses!