How to Wear Loafers in the Winter

Hi there and welcome! Between recent trips to the UK and Massachusetts, I’ve been wearing loafers with a lot of winter outfits. Shoes are one of the most important parts of an outfit when it’s cold outside. Loafers can make your entire outfit stylish and still keep your feet warm! I’m so excited about this post because loafers are a major part of my own wardrobe, and I always get questions about how to wear them when it gets cold outside. They’re actually a practical choice for winter!

I use affiliate links throughout this blog post, which means I might make a commission if you use my link and then make a purchase. This commission comes at no cost to you.

Today, I’m sharing a roundup of ways to wear loafers in the winter and keep your feet warm. If you’re looking for general tips on how to style loafers, check out my blog post on that topic!

How to Wear Loafers in the Winter: Tips, Thoughts, and Outfits

If you want to wear loafers when it’s cold but you aren’t exactly sure how to style them, you’ve come to the right place. You can style loafers with socks, sock tights, or tights to keep warm. If your loafers need to be broken in before they’re comfortable, socks or sock tights typically act as the perfect barrier to protect your feet from blisters. Below are socks and sock tights I wear or would wear with loafers.

First of all, Can You Wear Loafers in the Winter and When To Wear Loafers In the Winter

There are so many ways to wear loafers through the winter, and stay warm and stylish! Whether you prefer to wear jeans, a dress, or a skirt, loafers work with all different types of outfits when it’s cold.

Work Outfits

Loafers are obviously perfect for the office because they are the definition of a work appropriate shoe. They look nice with different types of work outfits, so you’ll get a lot of wear out of them. Plus, even loafers with a heel are more comfortable and practical than stiletto heels.

Travel Days

Travel outfits are meant to be comfortable in my opinion. Loafers can actually be just as comfortable as Ugg boots or sneakers, especially if you wear them with socks. I also love to wear loafers on travel days because it helps save room in my suitcase! It’s kind of like wearing your coat on the plane instead of packing it in your suitcase.

Weekend Outfits

Loafers are one of my go-to shoes for the weekend all year. They always help me feel a little more put together than most sneakers, and you can still keep your feet warm with socks.

Let’s Discuss Different Types Of Loafers

There are lots of different styles of loafers, and they’ll all work for your winter outfits! Some loafers look better with socks and some look better with tights. So, choose the loafers you love and just try them with different socks and tights. Here are just a few styles that are versatile for year round outfits.

Classic Loafers

Classic loafers are the style of loafers I recommend if you’re unsure if loafers work for you. They have a traditional, fairly flat sole and nothing too crazy on the top! Penny loafers are a great example of this style. Classic loafers go with most everything in your wardrobe, whether you’re getting dressed for work or something on the weekend.

Croc Loafers

Croc loafers are kind of a specific style of loafer, but I’m singling them out because of how they instantly elevate your outfit. They’re perfect to dress up a simple weekend outfit, but they’re work appropriate too. Croc loafers are that versatile – they honestly look nice with a maxi skirt as well as lounge pants. I’m wearing croc loafers in a lot of outfits throughout this post.

Loafers with a heel

These are perfect for work outfits or if you want to wear loafers with a dress. They’ll look best with sock tights or just regular tights. I’ve also worn the first pair with denim overalls, so you can definitely style them more casually or use them to elevate a casual outfit. If I were to wear this outfit in cold weather, I’d wear it with sock tights.

I’m wearing the first pair I linked below – the Rosie.

If You’re Wondering How to Style Loafers in Winter, Here Are 11 Outfits

Okay, here are full outfits!

Two-Tone Loafers And Matching Socks With Jeans

This is a go-to winter outfit for me, and it’s a classic look you can wear for a casual work day or out for holiday fun with your family like I am here. The cashmere socks I’m wearing in the photo below are the perfect thickness to wear with loafers. They aren’t too thick for shoes, but they’re really warm and soft. You can still wear socks with your loafers even if your loafers are two-tone like mine or have details on them. I’ve even worn the loafers below with fun salmon color cashmere socks. You can see that outfit here.

Gray Cashmere Socks and Croc Loafers

A gray sweater goes perfectly with brown or black loafers and gray cashmere socks. I chose these croc loafers to add a little texture to the outfit. I love how these gray socks and a gray top go with black or brown shoes. You can bring it all together by accessorizing in the same color as your shoes.

Lounge Pants and Loafers With Cashmere Socks

Loungewear and loafers might not seem like the most obvious pair, but it’s one of my favorite ways to wear sweatpants out of the house! This is what I wore for a long travel day from the Cotswolds home to DC.

Sock Tights And Croc Loafers

These sock tights are a wardrobe staple for me. In addition to actual socks, sock tights are the perfect solution to wearing loafers and flats throughout colder days. In this outfit, I’m wearing black sock tights with dark brown loafers, but the colors work together seamlessly!

Loafers And Sock Tights With Jeans

It’s also okay to have fun with sock tights! These are white with white polka dots, and they’re a fun detail to an otherwise classic outfit. Again, these are my go-to sock tights with loafers and ballet flats when it’s cold.

Black Loafers And Black Socks

Black patent loafers look really nice with black socks. I love how the patent stands out even more when you’re wearing socks. These black socks are a great option if you’re looking for socks that aren’t too thick.

These are black patent loafers I’d wear with this outfit. I own the second pair in a different color, which you can see in the first photo of this post.

Loafers And A Trench Coat

You can never go wrong wearing two iconic styles together: loafers and the trench coat. This is the perfect type of outfit for mild winter days or those days when it’s kind of rainy. I wanted this outfit to feel casual but elevated, so I just threw on these loafers with plain white trouser socks. This would also look cute (and probably better) with brown socks. I’m wearing my croc loafers that I’m wearing throughout this post, but this is a classic outfit that goes with any pair of loafers.

Winter Whites With Loafers And Sock Tights

You can also wear these sock tights with cream jeans or work pants for a monochrome outfit. This is my most worn button up! I’d go with the white polka dot sock tights I’m wearing above or the black pair. This outfit would be so cute with black patent loafers!

Patent Brown Loafers With Brown Socks

Brown patent loafers are the perfect option to wear with brown socks for a monochrome look. Don’t be afraid if they aren’t an exact match. It’s fun to mix and match different shades of the same color, whether that’s brown, green, grey, or another color.

Blazer And Loafers

Styling a blazer with loafers and jeans is another timeless outfit. You can wear this anywhere, including to work, a day out with your child’s school, or for a casual day-to-night look. This blazer has wool in it, so it’s pretty warm. You can easily wear this mockneck instead of a t-shirt to make sure you add another layer of warmth. I own this sweater and wear these together! I wear it under most of my blazers. I’m wearing suede mules in this photo, but this is an outfit I wear with loafers all the time.

I own these exact loafers in a different brown, and they’re super comfortable. If you’re walking a lot throughout your day, these loafers are my top recommendation. These loafers also come in navy, which would be so cute with these navy socks!

Business Casual Outfit With Socks And Loafers

This outfit is several years old, but it’s still one I wear today. Classic black loafers and black trouser socks will never go out of style. A tweed blazer jacket makes the outfit look more elevated. This type of outfit is perfect for work if you work in a business casual office or any office where you can wear jeans.

Final Thoughts: Can You Wear Loafers With A Dress In the Winter?

Loafers do work with a dress when it’s cold. Here are a couple of tips to help style them together.

Choose Full Tights Instead of Sock Tights

I’ve talked a lot about socks and sock tights in this post when it comes to loafers. But, if you wear a dress in the winter with loafers, I’d go for full tights for the most warmth and for style. Full length tights will ensure there isn’t a space between your dress and your legs, and they’ll help keep you warm.

Choose a Loafer With A Heel

Flat shoes and tights can be difficult to style with a dress in the winter. Sometimes it works but sometimes it leaves you feeling frumpy. So, a loafer with a heel is the perfect solution. As someone who doesn’t love high heels, I do love how many loafers come with block heels. So, your outfit will be chic and comfortable.

Did you find a way to wear your loafers when it’s cold outside? I hope you found some tips on how to style loafers and keep your feet warm! Let me know what you think in the comments.