Wondering how to style loafers this fall and winter season? Be inspired with this curated list of simple, chic, and classy loafer outfits for chilly days!
How To Style Loafers In Fall & Winter
Loafers may be trending for 2025, but this classic shoe style never goes out of style. Loafers add a chic and preppy touch to any outfit and are a great sturdy flat shoe for fall and winter when you want to wear something besides boots. These shoes are incredibly versatile, but avoiding the prep school aesthetic relies on careful styling, especially in chilly weather.
Ahead, I’m sharing 16+ stylish loafers outfits for women that are chic and easy to recreate. I’ll also walk you through the ins-and-outs of styling them for cold weather so you can start creating amazing looks from your own wardrobe!
Cardigan + cargo jeans.
get the look:
For a casual loafers outfit, take a page from Christal’s styling book. Above, she’s paired her fave Gucci Horsebit Loafers with an easy black cardigan and Agolde cargo jeans for an everyday look you can wear from Monday to Sunday! Elevate a simple outfit like this with a crossbody bag and dainty jewelry.
Style tip: Black loafers and white socks are equal parts academic and cool girl. It’s also a trendy and practical way to style your loafers in colder months.
White jeans, denim shirt + bomber jacket.
get the look:
Who says you can’t wear white in winter? White jeans and a white tee make the perfect neutral base to wear throughout the year, even during the cold months.
For chilly weather, layering with a denim shirt is practical and adds a subtle pop of color. Laman’s Source Unknown Bomber Jacket (here’s an affordable look-alike) perfectly complements the loafers and gives the outfit a vintage vibe. Just add a belt and a chic tote bag (like this Goyard one) to finish off the look.
Barrel jeans + chunky sweater.
get the look:
Loafers pair perfectly with the structured, tapered fit of barrel jeans. Gold details from Christal’s loafers, Chanel bag, and sunglasses complement the neutral turtleneck, giving the overall look a cohesive, polished feel.
I would totally wear this outfit to work, out for dinner, or for brunch on the weekends. Can’t wear jeans to the office? Simply swap them with a pair of trousers.
Mini skirt with tights.
get the look:
Wearing loafers with a mini skirt is a cute combination that you can make more fall and winter appropriate by adding thick black tights, a cozy turtleneck, and a long wool coat. Grab your chunkiest loafers for this look.
Chunky loafers bring an instant cool factor to any outfit, but they’re also practical for winter weather since the lug sole adds extra traction when walking through rain, snow, or slush.
Barn jacket + straight-leg jeans.
get the look:
For a fall trip to the farmer’s market, meeting up with friends, or window shopping, this next loafers outfit is one to copy. This look strikes the perfect balance between casual and elevated—I’m obsessed.
Here’s the breakdown: Start with a chunky turtleneck and a pair of straight-leg jeans. (If it’s really cold, layer a long sleeve underneath your sweater!) Next, add a barn jacket, this season’s “most-sought after outerwear” trend according to Glamour.
This trendy but ultra-practical piece is perfect for transitional weather and can be worn by country girls and city-slickers alike. The whole look comes together with a pair of loafers and a chic handbag.
With an oversized blazer.
get the look:
It doesn’t get much preppier than wearing your loafers with a blazer. Enter this next loafer outfit idea!
On cold days, layer a thick sweater underneath your blazer with cold-weather accessories like a scarf and leather gloves to stay warm. Laman kept this look from feeling too “corporate” with faded black jeans and a unique bag.
Style tip: Wearing black socks with black loafers will help keep your feet warm and elongate your legs.
Suede jacket + white denim.
get the look:
Get inspired by this next loafers outfit.
Pair classic loafers with white denim and a cozy sweater for a refined, minimalistic look. A suede jacket—a fall and winter must-have—adds texture and interest to an otherwise simple look. Likewise, a trench coat or leather jacket would also look amazing!
White tee + trousers.
get the look:
When in doubt, pair your loafers with pleated trousers for a classic yet cute ‘fit. A white tee shirt and black loafers make an elevated pairing you can dress up for work or down on casual days. Wearing a cropped (yet oversized) trench and a striped sweater over your shoulders perfectly complements the loafer’s preppy aesthetic.
Red sweater + jeans.
get the look:
In my opinion, there’s no better time to wear red than fall and winter. This season, team your favorite red sweater (like this cherry-colored cardigan) with a loose-fitting pair of denim and loafers.
The result is a chic but comfy outfit you can wear to everything from errands and coffee runs to late-night dinner dates. These Gucci loafers lend a more elevated vibe, while chunkier loafers would make it more casual.
Don’t forget to throw on a chic trench or wool coat before heading out the door!
Baggy trousers + chunky loafers.
get the look:
I love a loafer and trouser combo. But if you want a ‘trendier’ take on this classic combination, recreate the outfit above. Ting chose some baggy trousers from Cos and styled them with a plain white tee and a buttoned-front gray sweater.
Adding a chestnut suede jacket and mixed metal jewelry breaks up the cool-toned base and gives the whole look a trendsetter vibe. When it comes to loafers, opt for a chunky style. The chunkier, the better!
Sweater + trench coat.
get the look:
I adore this next loafers outfit. Keep it simple with straight-leg jeans, a gray sweater (layered over a white tee for an elevated touch), and a trench coat.
Add loafers and chic accessories and you’ve got the ideal look to take you from day to night.
Leggings, hoodie + wool coat.
get the look:
The unexpected shoe theory is an easy way to create cool, fashion-forward outfits. Essentially, the idea is that instead of going with the obvious shoe choice (in this case, sneakers), wearing an unexpected style like these Prada loafers will create a more stylish ‘fit. I love how loafers bring an elevated twist to a laid-back look of leggings and a hoodie.
Round out this street-style look with long socks, a cute shoulder bag, and oversized sunnies.
Jeans, sweater + denim jacket.
get the look:
If you want an easy-to-style everyday shoe, the Milan Loafer from Poppy Barley will become an instant favorite in your collection. They add a classic, slightly masculine touch to an outfit—not to mention they’re insanely comfy. Above is a great example of how Christal styles them in the chillier months.
This jeans-and-sweater-outfit has a casual feel, especially when paired with a denim jacket. But adding a pair of loafers instantly makes this go-to ensemble more elevated. Complete the look with a leather tote, your favorite sunglasses, and a latte in hand.
90s vibes.
get the look:
I can totally picture Monica from Friends wearing this outfit—it has a total ‘90s vibe! Recreate this Pinterest-worthy outfit by layering a black sweater over a white tee and grabbing your fave vintage jeans. Felicity’s jeans are the perfect light wash to contrast the black knit and oversized wool coat. Next, add a sporty element with a baseball cap.
I love how she mixed black and brown by adding a chocolate suede bag and these brown loafers from Alohas. Because both the bag and shoes have black details, it works perfectly!
Style tip: The pop of white from the socks brings additional interest to the outfit, but you could also swap them out for a cool pair of blue or burgundy socks that add a fun twist.
Vintage jeans, sweatshirt + trench.
get the look:
In my humble opinion, this is the perfect everyday outfit. This Anine Bing sweatshirt worn with vintage jeans is laid-back yet elevated. Using the sandwich method, Christal added a trench coat and coordinating tan suede loafers to round out the look.
Wear this combo on repeat by switching up the accessories and swapping the main pieces with other similar styles you have in your closet.
With brown accents.
get the look:
If you own a pair of brown loafers, this next outfit is a must-try.
I always recommend starting with an all-white base of a tee shirt and jeans if you don’t know where to start. From there, you can add different textures, colors, and silhouettes to build a trend-forward look. I love how Monika doubled down (okay, tripled down) on brown suede, accessorizing with a chocolate trench, matching suede loafers, and a tan bag.
Style tip: Pairing black socks with brown loafers seems like it shouldn’t work, but it totally does! This unexpected match adds contrast to the outfit and is a seamless way to pull in subtle black details from what you’re wearing.
Leggings + turtleneck.
get the look:
Wearing leggings with an oversized sweater is a timeless chilly weather formula that’s comfy enough to lounge in but chic enough to wear out and about.
Heading outside? Grab a black coat and coordinating accessories to make it look more sophisticated. If your sweater is in a neutral shade, like this gorgeous tan one, try matching your loafers to your sweater!
If you loved this article, don’t miss 21+ Chunky Loafers Outfit Ideas and 18+ Modern Womens Gucci Loafers Outfit Ideas for more inspiration!
