When September rolls into its second half, the weather begins to shift—warm days give way to crisp, cooler moments, and the world around us starts to whisper hints of autumn. It’s in these transitional weeks that we start thinking of ways to stay both stylish and comfortable, and charming loafer outfits emerge as the perfect solution.
Loafers have this inherent versatility—they can easily be dressed up or down, making them an essential piece for your wardrobe. I’ll admit, until I became a mom, loafers weren’t even on my radar. Sure, I owned a pair of brogues, but loafers? They just weren’t part of my shoe rotation. That was until I discovered just how effortlessly stylish and comfortable they could be.
While brogues can feel like an acquired taste—loafers are the comfort food of the shoe world, akin to a bowl of pasta or a slice of pizza. Everyone loves them. But despite their universal appeal, I know that styling loafers can be tricky. It’s one thing to include them in your capsule wardrobe, but when it comes to the question of what to wear with loafers, I get asked that more often than you’d expect. So, I’m here to answer that question and help you create stunning loafer fall outfits and cozy loafer winter outfits to guide you through the colder months.
Let’s dive into these charming looks and discover how to style loafers in ways that are both practical and chic. Whether you’re headed to the office, meeting friends for coffee, or running errands, I’ve gathered 13 different outfit ideas to inspire you.
What to Wear With Loafers
Fall Loafer Outfits
Fall is arguably the perfect season for loafers. The weather is just right, not too hot or cold, and the shoes blend seamlessly with the textures and layers we crave in autumn. Here are some ideas to help you elevate your fall style.
1. Classic White Button-Down with Jeans and Loafers
You can’t go wrong with a crisp white button-down tucked into a pair of dark-wash jeans. Add a chunky belt and slip into sleek loafers for a timeless and comfortable look. For an extra layer of warmth, drape a cozy cardigan over your shoulders.
what to wear with loafers
2. Sweater and Trench Coat Combo
Layer a soft, neutral-toned sweater under a structured trench coat. Pair this with cropped trousers and your favorite loafers for a chic, city-ready look. This outfit perfectly marries comfort with sophistication.
3. Blazer with Loafers
Blazers are a fall essential, and they pair beautifully with loafers. Opt for a slightly oversized blazer in a plaid or check pattern, wear it over a fitted turtleneck, and complete the look with straight-leg pants and loafers.
4. Mini Skirt with Loafers
For a playful, slightly preppy vibe, pair a mini skirt with loafers. Add a knit sweater or a button-down shirt tucked into the skirt, and don’t forget the tights if it’s chilly outside. The loafers ground the look, making it casual yet polished.
5. Trouser Skirt and Loafers
If you’re aiming for something a little more structured, a trouser skirt works wonders. Pair it with a fitted blouse or mock-neck sweater. Add loafers with a slight platform for that bit of extra height, balancing both comfort and elegance.
6. Loafers with a Long Dress
A flowy, long-sleeve dress paired with loafers makes for a stunning fall ensemble. Opt for earthy tones like olive, burgundy, or mustard to complement the season’s palette. Add a belt to cinch in the waist and a cropped jacket for a touch of warmth.
Winter Loafer Outfits
When winter arrives, the idea of wearing loafers may seem impractical at first glance. But trust me, with the right layering and pairing, loafers can still be a part of your winter wardrobe. Here are some cozy ideas to inspire your loafer winter outfits.
7. Oversized Coat with Loafers
One of my favorite winter looks is a wool oversized coat paired with tailored pants and loafers. The contrast of the structured pants with the cozy, relaxed coat creates a sophisticated yet comfortable outfit. Don’t forget to add chunky socks that peek out from the loafers for an extra layer of warmth.
8. Wool Tailored Pants with Loafers
Tailored wool pants are a winter staple. Style them with a tucked-in turtleneck or crewneck sweater, and finish the look with loafers. You can even layer a long, belted coat over the top for added sophistication.
9. Loafers with Tights and Midi Skirt
Yes, you can still wear skirts in the winter! Pair a midi skirt with thick tights and loafers for a feminine yet warm look. Add a chunky knit sweater or a tucked-in blouse, and you’re ready for anything winter throws your way.
10. Puffer Jacket with Loafers
For those days when it’s freezing but you still want to rock your loafers, go for a long puffer jacket. Pair it with slim-cut jeans and chunky loafers, and don’t be afraid to mix in some bold colors or textures in your outfit to keep it lively.
11. Knitted Maxi Dress with Loafers
A cozy turtleneck sweater dress is another great winter option. Pair it with loafers and wool tights for a streamlined, minimalist outfit. Add a scarf and a tailored coat, and you’ve got yourself a chic winter-ready look.
12. Layered Knitwear with Loafers
The key to winter dressing is layering. Try a turtleneck under a chunky sweater, paired with tailored pants or wide-leg trousers. Finish the look with loafers for a cozy yet put-together vibe.
13. Loafers with Wool Socks
Want to keep warm while still showing off your loafers? Invest in a good pair of wool socks that complement your loafers. Pair them with cropped jeans or trousers and an oversized sweater or jacket.
Loafers are truly the unsung heroes of transitional dressing. Whether you’re styling them for fall or winter, they offer an effortless blend of elegance and comfort. By mixing textures, layering thoughtfully, and incorporating seasonal staples like tailored coats or cozy knits, you’ll be able to craft charming loafer outfits for any occasion.
The key is to keep experimenting and playing around with different combinations. And remember, loafers are as versatile as they come—so don’t be afraid to think outside the box. Whether you’re pairing them with a feminine skirt or a sharp blazer, they’re sure to become one of your go-to shoes year-round.
