Let’s be real. A good winter coat can be a major investment. But if you choose wisely, the coat will last forever (or at least a good long time) and remain trend-relevant for seasons to come. Here’s my criteria for buying a new coat:

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.

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It happens like clockwork: each winter I haul out my boots and warmest sweaters and begin to sacrifice style bit by bit in favor of the comfortable and the cozy.

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.

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I know you don’t wanna even THINK about fall right now, but the truth is, September is just weeks away. The good news is, very soon you can start experimenting with some of the coolest trends this month’s fashion mags are featuring. I’m most looking forward to wearing big boxy plaids with cowlneck sweaters (like the look Adam Lippes sent down the runway for fall):

Statement accessories:

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

And all the pretty dresses!