30 Best Classy + Cool Loafers Outfit Ideas (2023)

There’s something about an outfit with loafers that my preppy heart can’t resist! 

Loafers are super comfortable shoes with a casual but sharp and sleek, tailored look. Dress them up with a skirt, dress or trousers. Or dress them down with jeans and even shorts. They easily go from work to weekend and you can even wear them with your favorite workout pants!

They’re a perfect option for fall and transitional weather since you can wear them with or without socks. And these slip-on shoes are a great option for busy mornings because you can just slip them on and go! 

Plus, there are a ton of different types of loafers so you can choose the style that best fits your personal style. From a classic loafer with timeless leather or suede. To penny loafers, tassel loafers, and “bit” loafers with a metal horse’s bit across the front. To more trendy platform loafers with a chunky lug sole heel. To casual open-back mule loafers, and shiny patent leather loafers. You’ll see brown loafers, white loafers, black, and traditional burgundy or “oxblood” loafers. And this season you’ll even see two-tone loafers, and ballet loafers as a hybrid of ballet flats and loafers with a rounded toe, low heel, and soft leather. 

Here’s a roundup of the best loafers for fall. 

SHOP THE LOAFERS

Are loafers in style fall 2023?

Loafers are definitely in style in 2023. Wear them with everything from wide-leg jeans to cropped jeans, to pleated wide-leg trouser pants, dresses, long skirts, pleated skirts, and denim skirts.

If you’re looking for loafer outfit ideas, I’ve got you covered! This post shows 30 looks with jeans, pants, skirts, dresses, and even shorts. 

I’ll be using my two favorite pairs of loafers, patent leather loafers with a chunky lug sole and creamy white loafers with a tassel and a black lug sole. 

Patent leather loafers, with their shine, draw the eye down to the end of the foot and grab attention in a sleek way. 

White loafers and boots are very current right now. White boots feel a bit too trendy for my personal style. But I can get behind white loafers. And especially white loafers with tassels and black soles. The black sole makes it easy to tie these loafers into a black outfit. 

In case you’re wondering about wearing white shoes after Labor Day, that’s a fashion rule that you don’t need to worry about anymore. If you love white you can wear it whenever you want, and that includes after the beginning of September. 

What outfits do loafers go with?

Loafers go with casual outfits from shorts and a tee, to jeans and a sweater, and even workout pants. Pair loafers with coated jeans and a cardigan for an edgy preppy look. Or trousers and a cardigan or double breasted blazer for a work look. Try a pair of loafers with a sweater dress and trench coat for a classic look or a denim skirt and blazer for a stylish look. 

Ready to dive into some outfits? Grab your loafers and let’s get started! 

Let’s start with loafer looks with jeans and pants. 

With jeans and pants

Pair your loafers with all styles of jeans and pants, from rolled boyfriend jeans to wide-leg jeans to flare jeans, bootcut jeans, kick crop jeans, straight-leg jeans, and even skinny jeans. They also work with wide-leg and straight trousers, and wide-leg and flared cropped styles of pants. Let’s take a look at outfits with a few of these styles of jeans and pants. 

A monochromatic look with white cropped wide-leg jeans, a cream sweater, and cream loafers

Call it cream, ivory, or ecru but it’s definitely having a moment. An outfit in all-one tone is super chic, slimming, and sophisticated. When I took the plunge and ordered these ivory tassel loafers, I knew I wanted to do an all-cream look. And this is so good! If you’re ever not sure what to wear, a monochromatic outfit is a great option. Notice how the black soles on these loafers draw the eye down to the foot. 

Similar Sweater | Loafers

With wide-leg jeans, a chambray shirt, and black loafers

Speaking of all one tone, here’s another look with a chambray shirt and wide-leg blue jeans. Wide-leg jeans have a laid-back and cool vibe. Do a relaxed roll on your shirt sleeves. The black loafers allow the hem of the jeans to casually spill long down over the top of the shoes not quite puddling on the ground. They create a preppy vibe with these laid-back jeans that creates a fun contrast. A black belt and bag ground the black loafers in the look. 

Loafers | Jeans | Belt | Bag | Similar Shirt

With a cream sweater, kick-crop jeans, and cream loafers

Here’s another laid-back preppy look perfect for a casual day. Notice how the long draping sleeves of this slightly oversized sweater and the cropped jeans create a laid-back vibe. Nothing is preppier than tassel loafers and I’m here for it. A black bag pulls in the black from the sole of the loafers. This pair of chunky loafers doesn’t get lost in this neutral outfit. Thanks to that black sole. 

Loafers | Sweater | Jeans | Bag

With wide-leg jeans, a long sleeve crewneck tee, a sweater vest, and black loafers

I’m all about finding new ways to wear pieces that I love. And this high neck short sleeve sweater vest is one of those pieces. I’m layering a crewneck long-sleeve white tee underneath for some visual interest. Black loafers and accessories round out the look.

Loafers | Jeans | Shirt | Sweater Vest | Bag

With coated wide-leg jeans, a cardigan sweater, and black loafers

Here’s an edgy preppy look, combining coated wide-leg jeans, a cable-knit cardigan worn like a top, and black patent leather loafers. The loafers are kind of unexpected here but they add a fun finish to the look.

Loafers | Bag | Coated Jeans | Belt | Similar Sweater

With kick-fit cropped jeans, a white tee, a striped button-down shirt, and black loafers

This is one of my favorite easy laid-back looks ever. I’m wearing kick-crop jeans with a white t-shirt and a navy-striped button-down shirt left open and untucked. Rolling up the sleeves adds to the easygoing look. But then the belt, loafers, and bag add a tailored and elevated look. It’s so good!

Loafers | Jeans (Regular fit, long length) | Bag | Shirt | Tee | Belt

With kick-fit cropped jeans, a black tee, a plaid trench coat, and black loafers

I can’t resist a trench coat and loafer look for double the classic goodness! This is a plaid houndstooth trench coat layered over a simple black tee and kick-crop jeans. A belt pulls the look together. 

Loafers | Jeans | Coat | Shirt

A red v-neck sweater, black cropped flare pants, and cream tassel loafers

This sweater is actually a deep red color and not orange at all. If you’re wondering what colors to pair with your cream loafers, of course, try a neutral color like gray or tan. But red, black, and cream totally work together too. The black soles tie into the black pants. Quilted bags are coming onto the scene for fall. I love how the quilting adds visual interest. And this one is a nice change from the smaller belt bags I usually wear. 

Loafers | Pants | Bag

With kick-crop jeans, a chambray shirt, a black utility jacket, and black loafers

I don’t know about you, but I spend a lot of time in the fall wearing my casual utility jacket. I’m stealing that monochromatic chambray-on-denim look from above. And this time pairing it with a black utility jacket. Notice how I’m casually rolling the sleeves of both the shirt and jacket to create a laid-back look. When you wear a column of color with a different color over top, the eye is drawn to the vertical column of color in the middle of the body. That draws the eye up and down and creates a slimming effect.  

Loafers | Jeans (Regular fit, long length)| Belt | Bag | Similar Shirt | Jacket

With straight jeans, a white button-down shirt, a brown leather jacket, and black loafers

This outfit is full of classic pieces. You’ve got the white button-down shirt, classic straight-leg jeans, and patent leather loafers. And then an edgy brown leather jacket and crossbody tote bag. Altogether it makes a fresh look. You can absolutely swap out straight jeans for skinny jeans if they feel more your style. 

Loafers | Bag | Jeans

With black cropped track pants, a half zip sweater, and cream tassel loafers

This casual outfit is so much fun and a great way to wear your workout gear in off hours! I love these cropped black track pants with a cream stripe up the side. I’m pairing them with these casual loafers and a pullover zip-up sweater. Wear this out to meet a friend for coffee. Or to casual outings like running errands around town. What can I say, I love combining sporty and preppy pieces together for an unexpected and fun look. Because we don’t have to do what’s expected of us. Right? Plus, these are such versatile shoes, they can be dressed up or down.

Loafers | Pants | Bag

With black wide-leg trouser pants, a white tee, a black and white striped cardigan, and black loafers

This good-looking striped cardigan from J.Crew never gets old! Here’s a perfect work look with black wide-leg dress pants, a white shirt, and this cardigan. With a pair of black loafers, they create a business vibe. 

Loafers | Similar Pants | Bag | Similar Shirt | Sweater

With black wide-leg cropped pants, a striped shirt, a trench coat, and black loafers

Here’s another work look with black wide-leg cropped pants, a striped shirt, and a trench coat. Black loafers are perfect here for creating a business vibe. Add a work tote bag and a black belt to finish the look.

Loafers | Similar Trench Coat | Bag | Pants

With black wide-leg, cropped pants, a striped button-down shirt, and black loafers

If you read my blog regularly, then you know that this is my favorite shirt of all time. This navy and white striped button-down from J.Crew is one that I wear all four seasons because it instantly creates a sharp and good-looking outfit. I’m tucking it into these black wide-leg cropped pants, adding a belt, loafers, and a work tote bag for a sharp look.

Loafers | Bag | Pants | Shirt

A chambray shirt, black cardigan, kick crop jeans, and black loafers

Adding a chambray shirt underneath this black cardigan creates a fresh look. You have a column of denim in the bottom layer with the jeans and shirt. Then pops of black in the accessories and the sweater. It’s a casual chic outfit!

Loafers | Jeans (Regular fit, long length)| Belt | Bag | Similar Shirt | Sweater

With a gray sweater, crop jeans, a navy coat, and black loafers

This is such a simple outfit. It’s a gray turtleneck sweater and kick-crop jeans. But there are two things that make it a look that pops. First, there’s a classic shoe with a touch of shine from the patent leather that draws the eye down to the loafers. And this navy double-breasted long coat makes a statement. It’s “extra” and eye-catching without being showy. We’re seeing statement coats quietly elevate simple outfits this season. And the understated refinement is so good!

Loafers | Jeans (regular fit, regular length) | Coat

With a black striped cardigan, black kick crop jeans, a white t-shirt, and black loafers

Here’s that black cardigan one last time. This time I’m pairing it with casual kick-crop jeans with a raw hem and black loafers. Notice how the gold in the buttons on the sweater matches the gold in the belt buckle and the gold hardware on the purse. That’s intentional and helps create a cohesive look. This is a perfect smart casual look!

Loafers | Jeans | Belt | Bag | Similar Shirt | Sweater

With a Breton stripe sweater, black wide-leg cropped pants, and cream loafers

Here’s another two-tone look, but this time with a collared Breton stripe sweater and wide-leg cropped pants for an easy fall work look. Yes, I’m kinda obsessed with Breton stripes. Stripes add easy visual interest. And since I’m smaller up top than on the bottom, stripes draw the eye across and my body looks more proportional. 

Loafers | Bag | Pants | Sweater

Now let’s take a look at skirt and dress outfits, and 1 shorts outfit. 

With skirts and dresses (+ 1 shorts look)

With a Breton stripe dress and cream loafers

One of the best ways to wear your cream loafers is with a Breton stripe. And in this case, I’m wearing them with my Breton stripe sweater dress. With black soles, it’s like they’re meant to be paired together. Adding the quilted crossbody bag creates a fresh, fun, and modern look.

Loafers | Bag | Dress (order “Tall” for knee length)

With a denim skirt, a white tee, a plaid blazer, and black loafers

This denim midi skirt reads like a pencil skirt and creates a classic silhouette paired with a white tee and Houndstooth Blazer. Black loafers and a black belt and bag add to the preppy look.

Loafers | Bag | Belt | Similar skirt | Tee

With a black skirt and a striped long-sleeve shirt, and black loafers

This next outfit is a simple look but it’s so sharp. Pair a white and black striped tee with a simple slip skirt and black, shiny patent leather loafers for a classic and good-looking work look.

Loafers | Bag | Shirt

With a black skirt, a puff sleeve sweater, and cream loafers

Here’s that same black skirt again but this time with a cream puff sleeve sweater and modern cream loafers making an eye-catching two-tone look. 

Loafers | Bag | Similar Sweater

With a shirt dress, a trench coat, and black loafers

I’m always looking for new ways to wear my favorite black shirt dress. Throw a trench coat over the top and these black loafers make the perfect work outfit that you could even wear to a casual business meeting. Grab a work tote to finish the look. 

Loafers | Similar Trench Coat | Bag

With a striped button-down shirt, denim skirt, and black loafers

Here’s another work look with that striped button-down shirt tucked into a denim midi skirt. The loafers, belt, and tote bag create a business vibe without being too stuffy.

Similar skirt | Belt | Loafers | Bag | Shirt

With a black mock neck sweater, denim skirt, and black loafers

Here’s an outfit that you can wear for transitional weather before the days get too cold, but when you still want a warmer sweater up top. Do a front tuck with the black sweater into a denim midi skirt. Add those loafers and a black belt to have an easy work look.

Similar skirt | Belt | Loafers | Bag

With a black shirt dress, a white blazer, and cream loafers

Here’s another two-tone look, but this time with my favorite black shirt dress, a white blazer, and those cream tassel loafers. Such an easy work look!

Loafers | Bag

With a belted black t-shirt dress, a Breton stripe sweater, and black loafers

I love to find all the unexpected ways to style a simple, black T-shirt dress. And here’s a good one. Belt the dress and add some black loafers and a black bag. Grab your Breton stripe sweater and throw it across your shoulders and you’re ready to go. This look is a little bit preppy from the loafers and a little bit country club thanks to the sweater around the shoulders. 

Similar dress | Similar sweater | Similar belt | Loafers | Bag

With a black turtleneck sweater dress, a trench coat, and black loafers

A trenchcoat is one of those classic pieces that make a look. Throw one over top of a simple black sweater dress, add some loafers and you have a smart look for work or an easy outing with friends.

Loafers | Similar Trench Coat

With a floral midi dress and cream loafers

Don’t count floral dresses out with your cream loafers! This floral midi dress has a Boho vibe that gets an unexpectedly classic finish with these cream tassel loafers. A cream belt and bag ground these classic shoes in the look.

Loafers

With a white blazer, white tee, black shorts, and cream loafers

Here’s another black-and-white two-tone look. But this time with a white blazer and a black pair of shorts. You can wear loafers in the summer months with shorts for a sharp look. And you can also wear an oversized blazer if that feels more like your personal style. This quilted black bag is a fresh and fun accessory.

Loafers | Bag | Tee

Loafers are a great addition to any wardrobe thanks to their stylish and sleek look and versatility. They are sure to be a hardworking member of your wardrobe!