How To Style Loafers For Fall And Winter

There’s one shoe in my closet that has truly stuck around for years. It’s the classic and timeless loafer. A slim-style leather or suede loafer, is truly one of those shoes that can stand the test of time. While sometimes chunkier options come in and out of fashion, or fun colors to make a bold statement, the loafer is a shoe you can truly invest in and wear for years to come.

Whether you’re into the traditional loafer or ones that are more trendy and chunky, loafers are truly a classic that have been around for nearly 100 years. It’s a timeless staple that’s great for dressing up or down from the office to business casual or just with jeans and a tee.

With so many style options, especially now from penny loafers, to platform loafers, or classic loafers, I wanted to share how to style loafers for fall and winter. And yes, you can 100% wear loafers in the winter when it’s cold. Let me show you all my favorite ways to style this closet staple.

How To Style Loafers

Layer With A Trench

Classic loafers pair perfectly with a trench coat. When it comes to style pairings, this is simply a classic. I find that loafers are ideal for that fall weather and a trench is a perfect coat to layer with it. It’s a smart casual combination that can take you to the office or the weekend.

Pair With A Cropped Pant

Whether it’s cropped trousers or denim, showing off your loafer with a shorter hem is perfection. Or style them with a skinny jean or straight-leg jean. I think they should be shown off whenever possible.

Style With Socks Or Tights

When wearing your penny loafers with a pencil skirt, shorts or skirts, try adding tights for a truly classic vibe. A cute ankle sock is such a 90s vibe too and can be a fun way to make them feel more trendy and less like a shoe for the office.

Not sure how to rock socks with your shoes? Check out my big guide on which socks to wear with what shoes.

More Fall And Winter Outfit Ideas With Loafers

How To Wear Loafers With Jeans

Jeans paired with loafers is hands down one of my go-to outfit formulas in my everyday life. You can wear this in the spring with a pair of light wash denim and a tee or tank. Wear this combination of a loafer and straight leg jean with a shirt and blazer for fall, or a cozy sweater. And for winter, just add a warm sock or a pair of tights under your jeans to keep those ankles warm. You can then add layers, coats and more for a winter outfit in jeans and loafers.

With Your Everyday Jeans

You can truly wear your laofers with everyday jeans for a casual and cool outfit. Simply pair straight leg, slim leg, or even a wide crop and full length option wtih loafers. Keep the rest of the look casual and you’ve got a great outfit formula.

Jeans And A Button Up

One of my go-to outfits for fall is simply my favorite pair of straight-leg jeans styled with loafers with a good button up. I love this oversized button down with it for a smart casual look that still feels put together yet a bit casual.

Styling loafers with your go-to jeans and so simple and easy. Try a straight leg jean, kick crop, or even a wide leg fit.These Coach loafers are a closet staple. I style them with so much and they are insanely comfortable.

Classic Loafers With A Blazer And Jeans

This is anoutfit formula I rely on constantly. Classic loafers, good jeans and a blazer. Dress up the top underneath or keep it casual, that can really play up or down the vibe here.

Loafers with jeans can easily be dressed up or down, it’s just all about the styling choices here. Add dressier tops or third pieces to make them feel more dressy and polished. Or go a little more casual in tees and light jackets. The style of loafer also doesn’t really mattter. You can opt for a lug sole loafer or a classic slim style loafer.

How To Wear Loafers In Winter

Winter Coat And Scarf – Just Add Socks

Come winter, you may think you need to only reach for boots. But loafers are a great shoe choice even when it’s quite cold out. When the temps drop, and your ankles may be showing, just add a warm cozy sock. This is a great way to add color and texture to your outfit too. You can also do a pair of tights so that you’re getting an extra layer under your jeans too.

Classic Loafers With A Blazer Coat And Jeans

My go-to look if I’m going to wear a loafer. Easy jeans, love a good straight leg, and a blazer coat. Camel is classic paired with black loafers, but you can play around with prints and colors here if you like!

Loafers With Pants And Suits

Loafers With A Houndstooth Suit

I am loving this 9-5 look of a perfectly fitting houndstooth suit with a straight cigarette leg. It’s so flattering and pretty. Instead of pairing your suit with yet another high heel, I’m loving a great loafer with it instead. Such a professional combination that also feels a bit more stylish and edgy.

You can also pair your loafers with a longer length trouser that hits the ground. I would opt for a slimmer style loafer again so taht there isn’t any bulk at the bottom.

Barrel Utility Pants And Loafers

The barrel pants trend is quickly becoming a must have bottom in your closet. Whether you go with a denim pair, or a utility option, these pair nicely with a loafer. I prefer a slimmer style here to balance out the weight the barrel can sometimes have in the leg. Add a third layer and you’ve got a complete outfit.

Loafers With Skirts And Dresses

Anytime I want to wear a fall dress or skirt, I swear that loafers are one of the best pairings. You can also add a little sock to the look to make it feel even more styled and interesting. Here’s some favorite looks of loafers paired with skirts and dresses from spring to fall and even winter.

Platform Loafers With A Fall or Winter Dresses

For that in-between fall weather, a sweater dress is perfect. And if the weather is a bit too chilly, just add some textured tights to complete the look.

Get The Look

Loafers With Mini Skirts

A great fall transitional outfit is to pair your loafers with mini skirts. Add a little black or white ankle sock to make it feel a bit more on trend.

This leather mini skirt paired with a blazer and turtleneck is such a classic look for fall and winter. You can also swap the sock for a pair of tights to add some warmth for the cooler winter months.

These are also great for spring too. I find myself reaching for loafers with mini skirts and light jackets all the time when the weather is in that in-between cool and warm stage.

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