How To Wear Men’s Loafers With Pants AND Shorts: 5 Outfit Ideas!

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Trying to figure out how to wear men’s loafers? They do look dressy, so you might think they should be reserved for suits and other formal outfits. But that’s not true at all!

Loafers are actually on the more casual end of the formality spectrum, when it comes to leather shoes. In this article, I’ll show you exactly how to wear loafers, and give you five different outfit ideas you can try (with pants, and yes, shorts too).

The loafers we’re thinking of for the outfits we’re laying out in this post are the Beckett Simonon Roy loafer.

These are the ideal style of loafers if you’re new to wearing them in general. They can swerve more dressy thanks to the slim silhouette, yet they’re inherently a bit more casual.


Well… it’s a loafer, not a classic dress shoe. (Refer back to our Spectrum of Style Formality post for a refresher.)

While black leather is certainly an option, the rich medium brown color you see here (and a heck of a lot of other places) is more casual and ready for spring / summer, or any time of the year, really.

Tan, or Cognac, is another great option, as it’s an even lighter shade of brown.

How To Buy The Right Size Leather Loafers

In my experience, loafers run fairly true to size compared to, say, a big pair of winter boots. Though it can be tricky sometimes, because you have a lot of options as far as how you’re wearing your loafers.

You can go sockless, you can do no-shows, you can wear absorbing insoles, or you can wear standard cotton “dress” socks. That’s something to consider.

Many of the outfits we feature in this article are geared towards warmer weather, so you’re gonna be going with no-show socks or absorbing insoles.

How Loafers Should Fit

The best way to tell if your loafers are too big for you is if your heel slips out of them when you take a step.

Another way to tell is by paying attention to the amount of room around your foot inside the shoe. Too much room, and you’ll be slipping and sliding, which means they’re too loose… Too tight, and of course, that’ll be uncomfortable in the long term.

Grey suede penny loafers and light wash denim with a linen shirt, loafers with no show socks
Grey suede penny loafers and light wash denim with a linen shirt

Also keep in mind that your feet expand throughout the day (due to blood flow, being upright, standing, eating, drinking, etc.) So if you’re shopping for loafers, try them on in the afternoon when you’ve already been out and about for a while.

That way, you can be more certain that the loafers you choose will be comfortable even when your feet are slightly larger in size.

How To Care For Your Leather Loafers

Caring for your leather loafers is pretty straight-forward, and you’d treat them like you would any other leather dress shoe.

Step 1: Make sure to condition and shine them regularly.

This will keep that leather rich and supple – perfect for wearing those bad boys in dressy situations.

Brands like Kiwi offer inexpensive, easy-to-use shoe shine kits that come with everything from brushes to shoe shine towels. But if I were you, I’d go with the kits from Saphir; they’re a much higher quality option.

I’d say a good brush once a week to get rid of any dust and dirt buildup, and a condition + polish every 3-4 weeks. It really depends on how often you use your shoes, but that’s a good place to start.

five ways to wear the chukka boot
Have you read the rest of this series?

Check out all Five Ways To Wear One posts

Step 2: Always use cedar shoe trees.

Putting cedar shoe trees in your shoes after a long day will help your loafers keep their shape while minimizing any odor and moisture.

So, that’s all sorted. Ready to step into some outfits? We’ll keep the style turned up and the puns turned down.

Men’s Loafer Outfit #1: Crisp And Continental


At first glance, it might seem like this outfit has too much going on – loafers, printed shirt, plus a denim jacket?

Hear me out.

If you’ve never given garment-dyed denim a look, spring and summer is the best time to do so. The color is a change of pace from dark denim and pairs nicely with a sturdy denim jacket.

A printed short-sleeve shirt in a slim fit is always a sure move for warm-weather style. Smart accessories like a heritage-quality belt and wallet complement the loafers perfectly.

Working loafers into ensembles that lean more casual are a good way to take advantage of that high / low style.

Men’s Loafer Outfit #2: Sharp & Suited

Five Ways to Wear One: Leather Loafers

Here we combine sharp tailoring with an equally sharp pair of loafers. It’s a step away from rocking sharp wingtips. This look will come off perfect at an outdoor wedding or a day at the office (don’t forget loafer socks, though).

For the spring and summer months, a classic navy suit serves you just as well as it would the rest of the year. Ditching the tie gives the whole ensemble a slightly more casual vibe, particularly with that crisp white shirt.

Stylish touches like an outstanding dress watch finish off this outfit quite well. Keep in mind that when you go with simple, tailored basics, it’s perfectly fine to rock a bit more of an eye-catching timepiece.

Men’s Loafer Outfit #3: Easygoing Summer’s Day

Five Ways to Wear One: Leather Loafers

Think stylish leather loafers can only be rocked with a suit or chinos and a blazer? Step outside the box and pick up a few upgrades over standard casual fare.

An upgraded casual T-shirt is a subtle way to switch things up from a slim pocket tee (although that would also work here). Tailored khaki shorts tie the look together with spring and summer vibes.

Clean sunglasses and a go-to casual watch are the finishing touches that make this outfit work. Add a sharp spring jacket if you need something extra.

Men’s Loafer Outfit #4: High-Low Style


Combining navy shorts with leather loafers is nothing new. The supporting pieces take this casual ensemble up a notch, another great example of high / low.

A baseball tee offers old-school athletic inspiration, while a navy quilted jacket (optional, of course) adds a monochromatic factor and hybrid style—part field coat, part rain coat.

A clean, simple watch with a striped NATO strap splashes some color in an unexpected place. The classic Aviators are always a good sunglasses option.

Oh, and the loafers stand out just enough. It’s tough to beat white sneakers in this case, but loafers are a much more refined (and unique) option.

Men’s Loafer Outfit #5: Travel-Ready

Five Ways to Wear One: Leather Loafers

When you’re traveling between climates or seasons, sturdy, solid layers are your saving grace. Once again, these handsome loafers complement a classic pair of dark denim perfectly.

Easygoing staples like a clean white Oxford and a washed indigo crewneck are layering pieces that play off the dark denim perfectly. The grey linen jacket is simple and stylish; it’s also effective at keeping out chilly breezes as you move from place to place.

Mix things up with a webbed stripe belt and finish with a timepiece. This just might be the only watch you’ll need for a quick trip – it’s that versatile.

The Take Away

Don’t forget: one essential item – in this case, really well-built loafers – can help tie together an entire outfit.

That goes for casual ensembles as well as seasonally appropriate suits. And for those in-between situations, a crisp leather loafer can act as a casual middle ground just like a simple white leather sneaker.

Don’t be afraid to push the boundaries and mix some of the above pieces together—a baseball tee under a slim chambray suit, for instance. Or a graphic tee under a denim jacket. A good pair of loafers grounds each look (pun very much intended).

Loafers with an upgraded silhouette and rich leather tones deserve a place in your spring/summer footwear rotation. It will be a relief to finally slip into them after months of thick boots and chilly temperatures. Start with these outfits to create your own stylish ideas.

Was that helpful?

Hopefully this article proves that learning how to wear men’s loafers (with both pants and shorts) isn’t as tough or confusing as it seems!

Tell Us: What outfits would you put together with these loafers? Are there any looks you’d add or switch up?

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