Men’s Loafers Outfit Inspiration: 25 Cool Looks For 2023
Here's what to wear with all your loafers, whether they're penny, tassel or chunky lug soled versions.
Loafers are a timeless and versatile footwear option that can be dressed up or down, adapting to any occasion. But while they might seem simple to style, the way you wear your loafers – and what you wear them with – will make or break your look.
One of the key debates when it comes to loafers is whether to wear socks or not, and here we will explore both options, offering guidance on how to pull off both looks. In addition, we’ll showcase a variety of stylish and on-trend outfit ideas featuring loafers, from business-casual ensembles to more laid-back weekend getups.
Whether you’re a seasoned loafer-wearer or just starting to incorporate them into your wardrobe, this article will provide you with the inspiration and guidance you need to get the most out of this classic shoe.
Do you wear socks with loafers?
The question of whether to wear socks with loafers comes down to personal preference and the occasion. While traditionalists will argue that loafers should never be worn without socks, going sockless is not only more comfortable and appropriate in warm weather, but has also become an extremely popular look over the past decade. (You can thank those well-dressed Italians for that.)
That said, for formal occasions and professional settings – think the office, business meetings and the majority of weddings – socks are best worn. Going without can look sloppy and unprofessional and fall foul of many dress codes, so if you’re in any doubt, it’s best to pull on a pair.
Confusingly, ‘sockless’ doesn’t mean wear no socks at all, however. Going without is not only unhygienic, seeing as socks act as a barrier between your feet and the shoes, preventing sweat and odour build up, but encourages blisters and other foot irritations due to your skin rubbing directly against the sole and upper. The trick is to wear ‘invisible’ liner socks, which offer a layer of protection but still give the appearance of going sockless and allow you to feel the breeze on your ankles.
Loafers with jeans outfits
With roots in American college campuses and Ivy League institutions, it’s no wonder the loafer works so well with another preppy staple: jeans. Yes, loafers have long been the perfect punctuation to a preppy outfit, working with every type of wash from pale through to raw denim.
When creating outfits with jeans and loafers, you should look to reference this collegiate heritage, teaming them up with sporty attire and traditional fabrics such as wool and tweed.
Quarter-zip sweater with jeans and loafers
The quarter zip is a smart casual go-to for lovers of preppy style, looking just as great layered over an Oxford shirt as it does a tee. Here we take a tonal approach, combining a navy version with mid-wash jeans to set a blue base that most men should feel comfortable wearing.
With a slight turn up and the socks left at home, the black penny loafers add a nice contrast to both the model’s skin colour and the lighter denim above it.
Jeans with a blazer and loafers
A blazer worn with jeans can look a little middle-aged dad if you don’t get the balance right, but this outfit does just that. Opting for a well-fitting sports coat in a thicker, heavyweight fabric like wool complements the rugged nature of denim, meaning it looks purposeful and not like you threw on the nearest jacket you could find.
Finishing off with relaxed pieces like a T-shirt and burgundy penny loafers also ensures that the jeans don’t stand out like a sore thumb.
Jeans, varsity jacket and loafers
Taking an athleisure approach to preppy style, this look takes the humble mid-wash jean and elevates it using a luxurious varsity jacket in silk and ribbed cotton as well as rich chocolate leather tassel loafers.
It’s ideal for those times where you want to look laid back yet still put together, such as weekend dates or drinks with friends. The definition of quiet luxury.
Raw denim jeans, shawl cardigan and loafers
This is an outfit that transcends time. It’s the type of look that references the style icons of the past – guys like Steve McQueen, Robert Redford and Daniel Craig’s Bond – yet still looks completely modern and of the moment.
Not only that, it’s a fit that all men can pull off, no matter their age or confidence levels. Simply take a pair of straight-cut raw denim jeans and a crisp white T-shirt, throw on a rugged cream shawl collar cardigan and finish with dark leather loafers.
Simple, timeless, masculine – what more could you want?
Workwear with jeans and loafers
Jeans have long been closely tied to workwear, so if you’re not a fan of Ivy League style and would prefer something more rough and ready, look to team up your denim with other workshop staples such as flannel shirts and canvas chore jackets, as shown here.
This time, the softness of the suede loafers offers a nice counterpoint to the rugged items above, helping elevate and polish the aesthetic slightly.
Loafers with shorts outfits
For many, loafers are considered the ultimate summer shoe, which makes them the perfect fit with a pair of shorts, whether you’re tackling a heat wave at home or jet setting off on vacation. Below you’ll find some outfits that are ideal for both, with the slip ons bringing a sense of sophisticated Riviera flair to each look.
Light separates with loafers
Whether it’s a garden party, high summer work event or a Caribbean wedding, a pair of tailored shorts with a light-coloured blazer is an excellent combination that looks smart and sophisticated but keeps you from overheating.
Here, the beige shorts contrast nicely with the bright white sports coat, with the similarly striped tee tying top and bottom together perfectly. Meanwhile, the rich leather loafers bookend the outfit, setting off any tan you may have.
Breton top with loafers
The Breton stripe top is a summer perennial that will never go out of style. Team a classic navy and ecru sweater like this with white chinos shorts and you have a modern, nautical-inspired look that’s ideal for relaxed lunches or alfresco dining on the marina.
Slip into a pair of brown leather penny loafers for a refined finish.
Swim shorts with loafers
If you’re on vacation and unsure exactly where the day may take you, go for a pair of mid-length, tailored swim shorts. As proven here, they can be dressed up or down depending on what you’re doing, taking you from pool to bar and back again without the need for a change.
Loafers are a smarter, chicer option than slides or flip-flops, yet just as comfortable and practical.
Preppy shorts with loafers
Loafers are an Ivy League go-to, and this outfit is the embodiment of warm-weather preppy style. The pastel blue shorts and pink vertical striped shirt are a bold combination, sure, but they work well together and are grounded by the chocolate brown leather tassel loafers.
Note how the shirt being tucked keeps it from becoming overbearing, while the belt perfectly complements the colour of the shoes.
Pleated shorts with loafers
This outfit takes what is quite a simple base – off-white shorts, white shirt, brown suede loafers – and turns it into something altogether more interesting and individual.
The green chunky shawl collar cardigan is on trend and makes for a great makeshift piece of outerwear on dry spring and summer days, while the addition of a pleat to the shorts gives them an elevated feel that chimes perfectly with the loafers.
Loafers with a suit outfits
Although Derby and Oxford shoes might be your first choice for matching with tailoring, the loafer is just as adept at being worn with a suit. Whether it’s highly polished leather penny loafers combined with a classic charcoal two-piece, or a pair of suede tassel loafers providing the finishing touch to unstructured separates, slip-ons shouldn’t be disregarded for your next formal event.
The key when wearing loafers with tailoring is matching the formality; the outfits below get the balance just right.
Blue lounge suit with loafers
Everything about this outfit is classic and office friendly: the blue sharkskin material, the perfectly tailored fit, the classic white shirt and patterned tie combination. The only thing that sets it apart from the rest of the rat race is the choice of shoe.
It just goes to show that a structured, well polished leather loafer can be worn with even the smartest of two pieces without taking anything away from the ready-for-business aesthetic. We love the addition of a turn up, which finishes just above the shoe, allowing the loafers to shine (literally and figuratively).
Green suit with suede loafers
Any unconventional suit colour is better matched with slightly more relaxed footwear, as proven here. Ideal for a summer wedding, this striking green two-piece is perfectly fitted and makes an impression on its own, which is why you don’t want to try too hard with your surrounding items.
A white shirt, tonal plain silk tie and dark brown suede loafers ensures there will be no vying for attention.
Corduroy suit with loafers
A loose, unstructured suit like this needs to be teamed with equally relaxed pieces, which is where the loafer steps in. The simple white Oxford shirt and black leather penny loafers help anchor both the top and bottom half of the look, allowing the rich blue corduroy fabric to take centre stage.
With cord traditionally associated with fall and winter, the addition of textured wool socks (again neutral) offers a nice point of interest that contrasts yet complements the overall aesthetic.
Navy blazer, grey pants and loafers
A navy blazer worn with grey tailored trousers is an all-time great separates combo that never fails and looks great on every man, which is why it’s so popular.
But it’s the finer details that set this look apart, such as the navy tie and socks tying together the top and bottom halves, and the rich navy leather loafers offering a point of difference to classic brown and black options. Classic with a twist.
Summer separates with loafers
Opting for a light, earthy palette in summer is a foolproof approach that always works. Here, shades of white, tan, beige and cream are used to create a coherent outfit that requires very little thought when combining all the pieces together.
Being a hot-weather look, suede is the obvious choice for your footwear, and leaving the socks at home keeps things breezy and relaxed.
Chunky loafers outfits
Chunky soled loafers are a key men’s shoe trend for 2023, with many prominent brands strapping huge commando lug soles to what is traditionally a sleek, low-cut silhouette. The addition of an oversized sole is not only practical, offering extra grip in the wet, but it transforms the loafer into something different altogether. No longer is it the streamlined, sophisticated shoe you’d see strolling along the boardwalk of the Cote d’Azur; instead, it oozes attitude and brings an edge to any look.
With that in mind, you should should be looking to wear chunky loafers in casual, grungy or streetwear fits – they will jar against anything too tailored and ‘proper’. Here are some examples to get the creative juices flowing.
90s grunge outfit with chunky loafers
You don’t have to go down the American prep route when wearing loafers with jeans. A chunky-soled black pair is the ideal choice for a grungy spring outfit consisting of distressed acid wash denim, a white tee and black flannel shirt, bringing a touch of 90s grunge to your look.
Club night chunky loafers outfit
An all-black outfit is ideal for wearing to a club – it looks slick, it’s effortlessly cool and it conceals any spilt drinks, making it both a stylish and practical approach.
Here we have a perfect summer night out getup: slim black jeans and a knitted polo shirt set a smart casual base, keeping you the right side of any dress code, while a pair of black chunky loafers (sans socks) brings a welcome edge to night-time attire.
Preppy staples with chunky loafers
Here we bring the preppy aesthetic bang up to date by subtly tweaking the core components of the look: the khaki chinos have been cut wider and are slightly cropped, which show off the the on-trend, chunky sole loafers beneath. These two minor adjustments give the look a more contemporary feel that’s more Aime Leon Dore than Brooks Brothers.
Up top, a fitted quarter-zip sweater keeps things presentable and offers the chance to play with your neckline silhouette.
Modern skatewear with chunky loafers
Taking its lead from the likes of Noah NY and the aforementioned Aime Leon Dore, this elevated take on streetwear sees a relaxed washed hoodie and MA-1 bomber jacket counterbalanced by a pair of sharply cut chinos and chunky loafers to create a high-low fit that feels particularly of the moment.
The earthy, tonal palette helps tie everything together, while the addition of stark white socks and a wallet chain introduce the skate-inspired elements that keep the look authentic.
Rockabilly outfit with chunky loafers
This superb outfit harks back to the rockabilly and greaser era with its all-black palette, bowling shirt and Michael Jackson-esque white socks.
Ideal for the spring and summer months, particularly nights out, the addition of the chunky sole loafers, white sport socks, minimal penchant necklace and wallet chain take the fit to the next level, transforming what would be quite a basic getup into something that has points of interest from top to bottom.
Smart casual loafers outfits
Aside from a Derby, the loafer is arguably the best smart casual shoe there is. Bringing a relaxed yet elegant finish to any look, they’re able to be dressed up or down for any occasion.
Below we prove the versatility of this must-have slip-on by showcasing a range of put-together outfits that will take you from business casual office to first date to drinks with friends.
Summer smart casual
When temperatures rise, how do you stay looking smart without self-combusting? The answer lies in the materials you choose. Here, a lightweight, short-sleeved cotton shirt is tucked neatly into a pair of breathable green linen pants, creating a sharp, sleek fit that won’t have you overheating.
Finish with a pair of relaxed brown suede penny loafers (sockless, of course), your favourite sunglasses and a straw fedora and you have a sophisticated high-summer outfit that works for beach weddings and garden parties alike.
Business casual loafers outfit
Although you may not have considered them before, loafers can be office appropriate. Pick a smart penny silhouette in a dark rich leather, like above, and they can be teamed with all your business casual staples, including tailored wool pants, Oxford shirts, cashmere knitwear and unstructured blazers.
Don’t forget your socks, though.
Riviera-ready loafers outfit
Suede loafers evoke images of well-dressed Italians vacationing in Monaco and Saint-Tropez. And you can introduce a touch of Riviera refinement to your summer looks by combining a pair of suede loafers with nautical-inspired pieces, as shown here.
White pants are easier to wear than you might think. Make them the focal point of your look by combining them with dark surrounding pieces – such as this navy/white striped shirt and navy shawl collar cardigan combo – for a sophisticated approach to holiday attire.
Cold-weather smart casual loafers outfit
Loafers aren’t just for summer. Worn with socks they can work all year round, even in the colder months. For example, team a tassel design with navy pleated wool pants and a merino wool turtleneck, like above, and you have a fit that will take you from office to bar without the need to change.
Drawstring trousers with loafers
Drawstring trousers are the item you didn’t know your wardrobe needed. Fusing the clean, sleek lines of dress pants with the comfort of a sweat pant, pull on a pair and you’ll wonder how you ever managed without them.
Ideal for dressier off-duty occasions, team them with other athleisure pieces such as heavyweight tees, polo shirts, crew neck sweats and slim-fitting overshirts to create relaxed fits that look smart, not sloppy.