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If there’s one fashion dilemma I fully understand, it’s the ugly but warm shoe dilemma. It hits every winter when you don’t want to suffer frostbite, but every winter shoe option feels clunky and ugly. If you’ve never dealt with this before, congratulations on living somewhere with year-round warm weather. But if you’re anywhere that gets snow, you know exactly what I mean.
Luckily, fashion has caught up with cold weather girls, and there are finally some good chic winter shoes options.
What Actually Matters in a Chic Winter Shoe
Now that we know that a chic winter shoe exists, what do you actually need to pay attention to when choosing your winter shoes?
Shape
I know that considering the shape of a shoe might sound weird, but trust me, you already do it when you’re shoe shopping. The shoe shape means what the toe of the shoe looks like (round, pointy, almond, etc.), how the heel is structured (flat, stiletto, block heel, etc.), and the pressure points of the shoes (is it evenly distributed, do you feel like all of the weight is going into your toes). For many of these, it’s personal preference, but it is important when it comes to picking a chicer winter shoe.
Sole
If you’re only going to pay attention to one this in this post, let it be the importance of the sole of your shoe during winter. Have you ever put on a pair of shoes with no traction and your foot just slides across the floor? Yeah, you don’t want that during winter, especially when there is a high chance of ice. The sole of your shoe needs to have some sort of traction on it, so it grips to the floor. The best way to understand this is to look at the bottom of your workout shoes. See how there are grooves along the bottom of the shoe? That’s what helps to create the traction. If you look at the bottoms of many flats, you’ll see a flat, smooth surface. Those shoes have no traction and you’ll slip immediately on ice.
Material
Material is important because it’s what will keep your feet warm and dry. You want a fabric that’s sturdy and preferably waterproof (or it can at least be sprayed to make it water proof). So those mesh flats that you wore all summer? Don’t wear them during the winter. If you look at the tag of your shoes (sometimes the inside tongue of the shoe), it’ll tell you what materials the shoe is made of. Also, most brands will tell you if the shoe is waterproof or not. Unfortunately, if it doesn’t say it, it most likely isn’t.
Proportion
Remember how we talked about proportion in this post? Well it’s important for your shoes as well! You want your shoes to balance out the rest of your winter outfit and actually fit. Not overwhelm it or get lost in the shuffle. For example, skinny jeans with a a platform loafer are going to make your feet look much larger in comparison to the rest of your body. It’s better to pair them with something like a ballet flat or high boot.
The Most Flattering Winter Shoe Styles
Need a cheat sheet for picking the best winter shoes for women? I’ve got one for you.
The three styles below are the most flattering for the majority of your winter shoe needs.
Row 1: Black Boots, Brown Boots, Taupe Boots
Row 2: Brown Ankle Boots, Black Boots, Loafers
Row 3: Black Flats, Loafers, Mary Janes
Sleek ankle boots
Sleek ankle boots are a perfect option for a few reasons. First, they cover your entire foot (important). Second, even though they’re often fitted, you can still wear warm socks under your boot (which is key). Finally, the slimmer silhouette allows you to easily pair them with most outfits. They don’t contrast with skirts or dresses, and most pants can easily fit over them.
Lug Sole Boots (Sometimes)
I had to put the caveat of sometimes with lug sole boots, because it’s easy to go wrong with these. A lug sole boot has many of the perks of a sleek ankle boot, but the added benefit of extra traction on the sole. The trick to making sure that you don’t go wrong with these is to make sure that the lug sole isn’t so big that it’s turned your shoe into a platform. There should still be a break in between the heel and the front of the boot and the sole shouldn’t be taller than the toe part of the boot. Additionally, the more fitted the boot is to your foot, the easier it’ll be to pair with more outfits.
Dressy flats for winter
Dressy flats have a weird place in winter. If it’s snowy, wet, or slushy outside, you aren’t going to want to wear them outside. But if you’re someone who brings shoes to work to change into, you don’t want your foot to freeze. The way to avoid these dilemmas is to focus on three things: how thick is the fabric, how much of your foot does the shoe cover, and how sturdy is the sole? You want to make sure that your foot is decently covered by the shoe and that the fabric is a thicker and sturdier. You also want the sole of your shoe to be supportive enough that you’d be fine if you had to wear them outside with tights or socks on.
Winter Shoes That Age an Outfit (And What to Choose Instead)
To avoid shoes that are going to age your outfit, it’s important to avoid two things: overly sporty and poor proportions.
We’ve already talked about picking the right proportions for your shoes, so let’s talk about going overly sporty or trendy. Sporty styles can be fun, but the more the style is for working out, the less you’re hitting the chic side. For example, remember when those “dad” sneakers became popular? They were great for running or playing a sport, but would you want to wear them with a nicer outfit? Basically, if it looks like your feet are going to the gym later, those might not be the best shoe option. If you want to wear sneakers though, don’t worry! There are options that are sleeker and go with more than just your gym clothes.
How to Style Winter Shoes So They Look Intentional
Now that you’ve got the shoes, how do you style them?
Pant Length
Pant length is way more important than you would think. It’s not just that you want to avoid your pants dragging in the snow (I still have nightmares about when people did that in high school), but you want to make sure that the hem is hitting at the right spot. The problem however, can be that the correct spot can be different on different people.
So let’s make it easy, shall we?
First, I’m going to focus on skinny (or straight leg) ankle length pants and wider leg, full length pants. If you’re wearing a skinny or straight leg pair of pants with your ankle boots, then your best bet is to have the hem of your pants skimming the top of your boots (or even have a small gap between the two). However, if you’re wearing a flat, the easiest option is to have the hem hit right above your ankle bone. Next, for full length pants, you want the hem to either hit right below the ankle or rest between your ankle and toes. The bottom of your pants should NOT be touching the ground. If you’re really stuck, then take your pants and shoes to a tailor. They’ll be able to help you figure out where the best stop for the hem to hit is. (Harper’s Bazaar has a great article here about jeans and boots.)
Sock Strategy
You NEED to wear socks during the winter, but, it feels like sock strategy/trends changes so often that it’s hard to keep up. For instance, when I was growing up, you would only wear socks with your flats if your mom made you. But now, it can be cute to pair socks with your flats. Also, I grew up wearing no show socks with my sneakers, but now people like to have their socks showing (can you tell I’m a millennial?).
What you need to do here is whatever truly works best for you. If you feel ridiculous having your socks show, then don’t have them show. Stick to shoes where your socks are fully covered. If you want to ease into it, wear darker, solid colored socks with black flats.
Outfit Balance
Figuring out your outfit balance is much easier than your sock strategy. With your outfit balance, you can look at two things. First, do your shoes match the dressy/casual level of the rest of your outfit? Second, do the proportions balance out? Remember, a clunkier shoes with skinny pants can make you look like you’re starring in a 90s Steven Madden ad.
How Many Winter Shoes Do You Really Need?
Depends on who you ask! Not the answer you wanted, right?
If you’re really stuck on how many winter shoes you need, you can turn to capsule and packing logic. Packing (and capsule) logic say that at the end of the day, you really only need three pairs of shoes. What three pairs of shoes can be different depending on your lifestyle, but if you need a starting place, I would say that a good place to start is a pair of heavy snow winter boots (like bean boots), a sleek ankle boot you can wear to work, and a pair of flats that could be work or casual (so a sneaker or a loafer). Those three options will probably get you through the majority of winter with no problems.
Obviously, three shoes isn’t a hard and fast rule, so at the end of the day, pick whatever number works for you!
Are you still stuck on where your pants hem should hit? Do you want to try having your socks show? Do you need help figuring out what boots work best for your wardrobe? If the answer to any of these questions is yes (or if you have any other questions), let’s talk! You can sign up for a FREE consultation call with me or check out my styling services to see what works best for you.
