I cannot stress enough just how important layering up during the colder months is. Layer EVERYTHING UP. Layer sweaters, blouses, tights, leggings, pants, ANYTHING. If you're worried about being fashionable and cute, there are definitely fashionable and cute ways to work layering into your daily winter outfit. You can use thicker spring and summer dresses by layering thick knit sweaters over them and layering tights under the dress. Worried about your feet getting cold? Layer thick socks, preferably wool or cotton socks. And if they're longer socks, you can scrunch them down over the tops of boots or keep them nice and high for added warmth. You can do that technique with shorts even, just make sure that the shorts are at least thicker, I'd recommend thick wool shorts or lined pleather shorts. If you're more of a jeans girl, you can always layer patterned button ups under knit sweaters and you can still layer thick socks over your pants, just make sure they're not over-the-knee or knee-high socks, and you can layer that over the tops of ankle boots. When you've got your core outfit going, throw on a thick knit infinity scarf on and a waterproofed or lined coat on, preferably one with a hood. You can layer a simple peacoat or a nice cargo jacket. If you don't have a hooded jacket, carry an umbrella since those are always helpful in a pinch when you don't have a hoodie or anything.
For the winter, you're obviously going to be wearing different kinds of shoes from the shoes you'd wear in the summer and in the spring. For this winter, while most people are still fond of tall riding boots, I think that ankle boots, moto boots, and boots that stop midcalf are incredibly cute. If you're someone who'd rather wear sneakers, I suggest wearing waterproofed oxfords and for cute sneakers, I think Puma makes some cute sneakers and Asos has a cute collection of oxfords, although you might have to waterproof your oxfords yourself (it's not that hard!). Now you might be wondering why tall riding boots are not on my list of winter essentials and I get the confusion, I do, but I also feel like boots that go up to the knee or past it or just under the knee aren't universally flattering on everybody. I feel that that particular style of boot is flattering on a very particular body type, one that I know most people don't have and that particular body type is that of society's favorite body type for women: skinny. As someone who is short and has chubby legs, tall boots go completely against my body, at least in my opinion. Where I want to elongate my legs, tall boots stunts them, and where I want my legs to appear slimmer, tall boots make them appear chunky. So, I've found a cute alternative: ankle boots, moto boots, and just short boots in general. I can still stay warm in them, they're incredibly in and fashionable this season so every store is selling this particular style, and I think they can very easily transition from fall to winter to spring and even in the summer. It all just depends on how you style the boots which goes together very nicely with layering.
This is the part where I talk about socks, tights, scarves, and beanies. Honestly, the way I dress during the winter depends A LOT on the kinds of socks and tights that I wear under my clothes so I'll talk about that first. With socks, you always want thicker and longer socks. I've found that wool and cotton socks are the best during the winter and I've also found that if you have any ankle socks, it helps to layer those guys on top of tights and under the thick socks for added warmth and protection. And if you have longer socks, you can pull them up and over your knees for stylistic purposes and/or just to cover more of your legs. With tights, it's all about getting those great thick tights. These are the tights with high denier count (100, 120, and 200) hence the thickness. This year, I've found out about fleece-lined tights with a high denier count and while I only borrowed a pair and have yet to invest in a good pair for myself, that one day I borrowed those tights was incredibly cozy and warm. If you're worried about having to order online for tights, no need to worry, plenty of stores sell high denier count tights at affordable prices. My first pair of winter tights were from Target and they were $10 and lasted me 6 years before they started getting any sort of runs in them. With socks, you can shop for them at stores like Tilly's, H&M, Forever 21, and Asos. Now, scarves and beanies, you need both to be knit or made of a very warming fabric. I prefer infinity scarves just because they're very easy to throw on just before you're out the door and very easy to take off when you get inside. With infinity scarves, there are also less chances of any part of your neck area getting exposed to the winter air. With beanies, thick knit is always good because it's a good investment in something that you could be wearing a lot. And there are multiple styles you could buy the beanies in, you can get them with cute animal ears on them, with ear covers, or with tassles on the ends so you can pull down and tie your beanie (or hat at this point) more snuggly to your head. And sometimes, what tights, socks, scarves, and/or beanie you wear can determine just how warm and nice you look during the winter.
This one is less how to keep warm and more how to keep cute. For myself and a lot of other people, my skin takes a weird turn during the colder months. Where my skin is usually oily, it becomes dry and flaky during the winter so I have to change up my moisturizer and my make-up. With the rain and the cold hitting your face during the winter, you need to make sure that your eye make-up is waterproof. So always make sure to have primer under your eyeshadows so that your eyeshadow looks vibrant and bright against the starkness of winter's color palette. If you're wearing winged eyeliner, make sure if you're using liquid, that it dries matte and that it's a waterproof formula in case it rains and in case the cold wind blowing against your face makes your eyes water up, which brings up mascara which again, make sure it's a waterproof formula like Maybelline's The Rocket Waterpoof mascara. But if you're using a gel or a cream liner, make sure the formula is creaseless and that it really sticks to your skin. A good cream liner is the Urban Decay cream liner. I just recently invested in it ($22 D:) and it's a very nice and creamy liner that when used on top of eyeshadow primer, stays put. Water alone can't take it off, so I actually have to use a make-up remover to take it off, which is A+ in my book. For any sort of face make-up that you wear (concealer, foundation, blush, powder), you want to make sure that the makeup is moisturizing and that it doesn't settle into the fine lines and cracks of your skin, especially if you're applying concealer to your under-eye area. With your foundation, you want something, again, waterproof. Now, for things like blush and lips, most people get beautiful natural blush from the wind biting at their cheeks and most of the time, their lips will end up being the same shade. For those like myself however, I have to rely on blush to get any sort of color on my face. I'm really fond of cream blushes so I've been relying on my Stila Convertible Color in Dahlia and my Korres Cream Blush in Chara Crimson to give me that "windswept" color in my cheeks. Both cream blushes are hydrating and while the Stila one is a bit more dewy (I set it with a tiny bit of theBalm's powder blush in Toile), the Korres cream blush dries matte but is still moisturizing so I don't have to worry about my cheeks getting dry. With my lips, I rely on Carmex Lip Balm. I slather that stuff on any dry spots on my face at night after I show and moisturize which is normally my lips. When I get up in the morning, my lips are nice and soft and I apply some more Carmex while I get dressed and put my liner and blush on. Then when I'm ready to leave is when I apply any lipstick or lipstain. If you've noticed from my blog, I'm fond of plums, reds, and oxblood-type shades. Basically, for me, I rely on my cheeks and lips to get color into my face. If lipstick and lipstains aren't for you, there are a lot of fantastic tinted lip balms out there and a lot of them you can buy from your friendly neighborhood drugstore.
The other tips won't help if you don't take into account your daily life and where you are throughout your day. For example, if you're mostly indoors and only outside for a short period of time before hopping into your car or entering another building, you probably won't need to layer as much or take into account waterproofed makeup. However, if you're constantly outside for work, for school, etc. then you should probably pay attention to how much layering you've got going on or if you're going to need to wear waterproofed makeup. For example, I'm indoors most of my day. I'm either in class, at work inside, or inside at home or at my boyfriend's. I only ever have to be outside for when I'm getting in and out of my car. So make sure to take into account how often you're outside versus how much you're inside. It definitely helps so that you don't end up sweltering in class/at work or shivering while outside.