How To Wear Loafers With Jeans: 18 Outfits That Get This Combo Right
This once maligned duo has become a key part of sartorially inspired off-duty wardrobes, thanks to the rise of preppy 2.0. Here's how to nail the look in a modern way.
Loafers and jeans, once considered an unconventional pairing, or at least not cool, have seamlessly evolved into a stylish and acceptable combination in the world of men’s fashion. This fusion of classic and casual elements has found its home in the preppy corner of a modern sartorial renaissance, spurred on by a cabal of representatives seen biannually at the Florentine menswear shindig, Pitti Uomo.
It represents the epitome of versatility, making it a go-to choice for those seeking a refined yet relaxed appearance. The inherent elegance of loafers, characterized by their slip-on design and sleek profile, juxtaposes beautifully with the laid-back nature of jeans.
But let’s not forget that jeans have had something of a reawakening in recent decades, with the proliferation of Japanese selvage denim almost turning jeans in works of art in some cases. Yes, jeans have transcended their original utility as tough workwear pants, opening the door for smarter, cooler ways to style them.
When executed correctly, a loafers and jeans combo exudes the perfect blend of sophistication and comfort, making it a contemporary classic in men’s style.
When to wear loafers with jeans
If your wardrobe leans towards a sartorial aesthetic – that is, you like the bulk of your clothing to have been born from the hands of a tailor – then the combination of loafers and jeans is a sensible one for your off-duty, laid-back requirements.
The loafers bring the nonchalant dressy elegance to the party, while the jeans radiate a rugged charm. Whether you opt for classic penny loafers, tassel loafers or more contemporary chunky-soled designs, loafers can complement a host of different jean styles, from slim-fit to relaxed, making them adaptable to different preferences.
At the very least, loafers bring a sense of discernable craftsmanship to the look, with the ability to dress up a pair of jeans and make them look a bit more polished and considered. They bookend your outfit with a slim leather profile, adding a contrasting texture to denim. It seems your dad was on the money in the 70s all along.
How to wear loafers with jeans: general guidelines
Before you reach for the first pair of jeans you find in your wardrobe, there’s something of a skill in teaming them with loafers. Firstly, the correct fit is essential. Most traditional loafers are quite slender shoes so you want to choose jeans that have a slim tapered fit to create a clean and streamlined look. That said, contemporary chunky versions are able to accommodate a much more expansive baggy leg, but such a jean would drown a classic loafer.
The wash of your denim matters, too. Dark-wash jeans offer a more polished appearance, suitable for dressier occasions, whereas lighter washes or distressed jeans can lean towards a more casual, laid-back style.
That doesn’t mean that all light washes can’t be smartened up or that all dark indigo denim can’t be made to look casual, but as a rule of thumb, the darker the jeans, the smarter the look.
The type of loafer matters
Not all loafers are created equally, or with the same purpose, with some being smarter than others.
The classic penny silhouette is a pretty versatile shoe and will work well with a range of jeans. They are a good option for when you want a clean and traditional look with slim-fit and straight-leg jeans. They often come in modern chunky styles, too, giving you the option to wear straight-leg and even wide-leg fits.
Tassel loafers add a touch of flair to your outfit and are well suited for smart-casual looks – with a shirt and blazer for example. Both dark-wash and medium-wash jeans go nicely with the leather tassel loafer, while lighter jeans will be better suited to the more relaxed suede tassel loafer.
Horsebit loafers are a touch more difficult with jeans as the contrast can be jarring. Chunkier takes are the safe play, allowing you to wear them with contemporary, looser-fitting pieces.
Socks or no socks
The length of your jeans plays a very significant role in the end result of the look, because it will largely determine whether you wear socks or not. For full-length jeans where the hem comes to rest on the shoe, we would typically recommend wearing neutral-tone socks that don’t catch the eye.
For cropped jeans or jeans where you have a large turn-up, the sockless route is a good one to take as it creates a nice separation that makes more of the loafer. Alternatively, you can wear a statement sock, which might borrow from another color featured elsewhere in your outfit.
If you do opt for no socks, just make sure you’ve broken in the loafers, because there’s nothing worse than seeing heels that are a blistered, bloody mess. If you can find a pair of no-show socks that are actually invisible to the naked eye, then snap them up immediately – they will not only ensure your comfort but also help with hygiene.
18 stylish loafers with jeans outfits
Tan suede tassel loafers with white jeans
A great light tonal outfit for summer with a tonne of relaxed sophistication. The white jeans, although a demon to keep clean, are a great match for the beige polo, while the tan suede tassel loafers add a textured element that perfectly finishes the look.
Smart yet casual – what more can you ask for?
Black penny loafers with black jeans
We’re big fans of monochromatic fits just because they look great on just about everyone and are easy to style up.
Where most people falter is in their choice of shoes, but the inclusion of black penny loafers ensures this look remains polished, even though the silhouette is quite casual.
You could just as easily throw on a black blazer to dress it up a notch.
Black penny loafers with straight-leg jeans
While this look could just as easily have been bookended with some variant of sneakers, the leather penny loafers elevate it a notch, making it a touch more formal.
The turn-up on the jeans and the no-sock policy keeps the look feeling modern.
Suede grey loafers with light-wash jeans
Personally, we prefer the loafer option, especially in this case since the white soles combine nicely with the cream shirt.
Black penny loafers with grey slim-fit jeans
Combining the three non-colours of black, white and grey is always an excellent idea when trying to achieve a low-key level of casual elegance.
The slim silhouette throughout this outfit meant that some sleek black penny loafers were the obvious choice.
Chunky black penny loafers with dark-wash jeans
Understatement is sometimes the biggest statement when it comes to dressing with impact, as this look perfectly shows.
Shades of navy throughout complement the addition of the black loafers. The fact that they’re chunky gives the look some modern gravitas and places more emphasis on the shoes.
Chunky black horsebit loafers with straight-leg jeans
A super simple contemporary look that anyone can pull off: combine a plain white T-shirt with grey jeans and some chunky horsebit loafers.
Again, statement dressing is not always about garish colors or patterns. The addition of white socks works well here, coordinating with the tee and rounding off the look nicely.
Brown suede penny loafers with dark-wash jeans
A sophisticated approach to denim, this look utilizes a swish pair of tapered jeans with a dark indigo rinse and combines them with a regular beige cashmere crew neck.
Suede penny loafers were the correct choice, adding to the textural input of the sweater.
Oxblood penny loafers with straight-leg jeans
Oxblood is such an underrated shoe tone, doing the same sterling job as black or dark brown but with a little more character.
In this case, these oxblood loafers help to balance the vibrant blue tone of the relaxed straight-leg jeans and provide a nice contrast with the lighter tones up top.
Black penny loafers with cropped straight-leg jeans
It wasn’t that long ago that the fashion mob would have taken you to the woodshed if you’d been caught wearing white socks with loafers, but it has become a bit of a ‘thing’ in recent years.
This combo works well thanks to the complementary colors in the right of the look, plus the cropped trousers make the foot of the ensemble look like a style statement rather than an accident.
Black penny loafers with light-wash jeans
This combination of striped cotton shirt and regular jeans with a turn-up would usually call for a pair of suede tassel or penny loafers, but the choice of black loafers is a strong one, creating a solid contrast to tie up the look.
The preppy touch with the draped sweater hasn’t gone unnoticed either.
Black penny loafers with relaxed light-wash jeans
Cool as you like. You might be surprised to cast your eyes over this outfit and see it punctuated with a pair of loafers. Most guys would usually opt for sneakers or maybe chukka boots with a look like this, but the addition of black penny loafers makes a stronger statement.
A quality black leather tote bag is the glue that binds it all together.
Suede beige penny loafers with cropped white jeans
Tonal alert! Not coming to an Italian restaurant any time soon is this wonder in beige, beautifully concocted to show off the inherent richness of nude and neutral shades.
Of course, the suede loafers are the perfect fit, being both tonally perfect and texturally interesting. This is how to do old money style in 2023.
Black horsebit loafers with light-wash jeans
There’s a lot to love about this outfit. Straight off the bat, the combination of Prince of Wales check blazer, jeans, crew neck and shirt is manna from preppy heaven, then the black horsebit loafers seal the deal with a touch of high-end elegance and class.
Black penny loafers with black jeans
Minimal and understated, the combination of the black straight-leg jeans and chunky black loafers gives you a tonne of styling options to go in every direction.
In this case, it’s a low-key, dark-tone vibe thanks to the navy tee and autumnal cotton shacket.
A straight-up everyday casual look.
Oxblood penny loafers with slim-fit jeans
Oxblood penny loafers in their element. The combination of the smart tapered jeans, navy tee and beautiful brown blazer could have been finished off with any number of brown shoes or boots, but the oxblood loafers bring something different and more interesting to the party.
Black penny loafers with indigo selvage jeans
Heavy selvage denim is the holy grail when it comes to jeans but many struggle with what shoes to wear with those bold turn-ups.
Boots and high-tops are often the first port of call, but as this look demonstrates, a pair of black penny loafers is just the ticket, especially when they’re complemented by a shawl-collar cardigan.
Brown tassel loafers with slim-fit jeans
Slim-fit jeans are the perfect shape for slimline loafers since they taper perfectly into the contours of the shoe.
These regular-wash jeans provide just enough of a contrast to make the loafers stand out, while the cream bomber jacket keeps the whole outfit looking modern.