The Ultimate Guide to Styling Penny Loafers for Men (12+ Outfit Ideas)

Undoubtedly, loafers are one of the best footwear ever that every man must own.

Although it has gained popularity, you may desire to have one. More than any other styled loafers, we’re especially mentioning the Penny Loafers for Men.

How can this uniquely styled slip-on become one of the must-have wardrobe staples for men? Because of the minimal style, attractiveness, and versatility, it offers. 

The stand-out option can be the Penny Loafers in a crowded place of oxfords, derbies, and chukka boots.

This classic slip-on goes with any outfit, whether a tailored suit or a smart casual outfit.

If you are about to try them for the first time, this blog post will help you. 

With a little styling, your penny loafers will soon be your favorite finishing touch for outfits that make you stand out while staying true to your style.

Penny Loafers Style – How it Looks

Just because of the unique style of penny loafers, it got so famous. But what does it look like? Usually, loafers are slip-on style so does the penny loafers.

Though there is a vast range of loafers for men available, you can find easily penny loafers with:

• You can see a small leather strap across the top of the vamp area (shoelace area), typically with a diamond-shaped cut-out.
• It’s a slip-on style shoe with a rounded-toe front
• The Mossain-style construction (Without heel and made of leather)
• Low heel and flat sole, provide comfort all-day

For your reference, here is the image of Penny Loafers:

It’s uniquely styled and versatile and allows you to wear it with any outfit you choose for any occasion.

That’s the specialty of Penny loafers, making it one of the must-have shoes for men to incorporate into their wardrobe.

Why you need to Incorporate Penny Loafers in your Wardrobe

My favorite footwear is penny loafers, I can start a debate if you ask me so Leave my words behind, Just consider surfing through the social media and Pinterest platforms for once.

You will see the popularity of Penny loafers.

From famous lifestyle YouTubers to style influencers, everyone incorporates penny loafers, making it their go-to style shoe for any outfit.

Even if some stylist wears shorts, they may be paired with penny loafers.

More than just pairing with a formal outfit, the penny loafer’s versatility allows you to wear it with any outfit you wear even if it’s a tailored suit or polo shirts and shorts.

Even if you have a limited budget invest in a nice shoe that goes with most of your outfit, you can choose penny loafers.

This is why you must consider incorporating penny loafers into your wardrobe. Moreover, it’ll never go out of style for sure.

Rules to Style Penny Loafers for Men

Though it’s just a slip-on style shoe, there are a few rules to style. Knowing these rules and style accordingly will for sure effortlessly make you look stylish.

Know When to Wear Socks

When you are wearing loafers, you should know when to wear socks and when to not. 

Mostly, everyone who opts for penny loafers won’t wear socks except if it’s a suit or professionally formal outfit. If you wear a dress shirt tucked into tailored trousers, you don’t have to wear socks.

Feeling comfortable without a sock means you can choose a loafer sock. And if you are opting for a suit, socks are a must as the skin will ruin your suit’s appearance.

Showcase the Right Way

Loafers are not like other types of men’s shoes. It needs to be showcased the right way to style. 

How to showcase? Let’s say, for instance, you are wearing chinos that have covered the loafers. Wrong, this is not the right way to showcase. 

You need to cuff the chino bottom to make the penny loafer style fully visible.

So, whatever bottoms you are wearing, you should cuff the bottom or crop the pants.

Leather Material

Leather is the ideal material for penny loafers. It’s quality and durability speaks volumes when you wear it. So, choose finely crafted premium leather or suede leather penny loafers.

Choose the Right Color

Finally, choose the right color penny loafers that compliment your outfit. However, you may be required to wear a belt. So, choose the belt matching penny loafer color.

How to Style Penny Loafers (Outfit Ideas for men)

You decided to style penny loafers but don’t know what to wear with them. 

No worries, here are the 12 Penny Loafers outfit ideas that go with any occasion.

Whether you are dressing up for professional office space or suiting up for business meetings, these men’s penny loafers outfit has everything you are looking for.

Penny Loafers with Dress Pants

One ideal way to style penny loafers is to wear them with dress pants.

Usually, dress pants are tailored to perfectly fit you. Where can you wear dress pants to? Office space, semi-formal settings, dinner, date night, or any other related environment.

Most commonly, dress shoes suit the dress pants. But to make an unusual option and add versatility to your dress pant outfit, you opt for the Penny loafers.

Choose a crisp white striped dress shirt, pair it with well-fitted grey dress pants, and finish the outfit with Black or white penny loafers. 

Although, you can layer it up with a cardigan or sweater. Also, you can play with colors like a maroon dress shirt paired with black dress pants, and finish off the outfit with black penny loafers.

Or a Blue dress shirt, and brown dress pants, and finish off the outfit with suede brown leather penny loafers. So, these men’s penny loafers outfits can be worn for any dress-up occasion.

Penny Loafers with Cuffed Jeans

Wearing jeans with penny loafers can be tricky to put together for men.

But, instead of wearing jeans like the old ways, you need to cuff the bottom of the jeans. This is the right way to wear penny loafers with jeans.

The straight fit of the jeans will cover your loafer style, limiting its style showcase.

So, when you decide to wear jeans with penny loafers, you need to consider a few things:

• Choose ankle-fit jeans or well-fitted jeans
• Cuff the jean’s bottom twice to reach above the loafers
• Make sure the penny loafer style is fully visible

In this way, you can style the penny loafers with jeans. You can pair the jeans with t-shirts, a polo shirt, or a casual shirt, and finish off the outfit with penny loafers.

You can opt for penny loafer for casual occasions like friend outings, casual dinner dates, social gatherings, informal events, shopping, and more.

Penny Loafers with Cropped Pants

Wearing penny loafers with cropped pants. It’ll completely showcase the penny loafers style and doesn’t require folding the bottoms.

Commonly, you have to tailor the cropped pants. How does it look?

It’s nothing but a shorter length than the classic one. Usually, it is cropped above or right equal to the ankle bone. This style of pants can fully showcase the penny loafers style.

Cropped pants can be worn for casual as well as formal occasions that don’t require you to be completely formal and professional. This style of pants will show your skin in a larger size unsuitable for formal. 

So, you can wear cropped pants with polo shirts, tucked-in dress shirts, and sweatshirts, and finish off the outfit with black or brown loafers. 

When you choose black penny loafers, make sure to try different color cropped pants. 

It’s fine to wear black with black but to enhance the look and make it different, you can try colors like khaki, tan, beige, navy blue, and so on. While choosing cropped pants, look out for a fit one.

Penny Loafers with Tailored Trousers

Alright, tailored trousers with penny loafers. Usually, tailored trousers can be worn for formal outfits but we’ve already seen many usual above.

Let’s play with some colors, textures, and patterns here. 

Instead of choosing random common trouser colors, try different colors like tan, olive green, maroon, khaki, white, beige, pebble, red, and patterns like stripes, checked, and textured.

Choose dress shirt colors that complement the trousers like white usually goes with any colors you wear, tan, navy, maroon, grey, olive green, khaki, and stripe dress shirts.

You can style penny loafers differently here, instead of choosing regular black, brown penny loafers. Choose double colors, suede brown, light brown, white, polished brown, navy blue, and so on.

Whether you are going to a professional office space or dinner date, you can opt for this outfit as it’ll make you unusual in a formal look.

Penny Loafers with Suit

I see people asking, “Can you wear penny loafers with a suit” Of course, yes, its versatility allows you to wear anything with it. So, you are suiting up for the professional business meet. 

Imagine wearing a nice navy blue tailored suit with a sleek white dress shirt underneath. Adding a brown leather belt and finishing off the outfit with well-polished brown penny loafers.

However, you may not only wear a suit for a business meeting. How about a nice dinner date with your Love? It’s not just about wearing a suit for a dinner date. 

If someone wants to know if you are a well-dressed guy, they will look at your shoes. It speaks volumes.

Wearing a nice tailor-made black, navy, and grey suit and finishing off the outfit with polished penny loafers for a dinner date showcases that you are respecting her presence.

It’ll make her instantly like you. Other than wearing normal shoes, wear well-polished penny loafers as they’ll enhance your look to be more well-refined.

Choosing colors, you have polished black, brown, maroon, blue, and more.

Penny Loafers with Straight Fit Denim

Wearing penny loafers with straight-fit denim can be tricky. 

Because the straight-fit denim will cover your penny loafers style. However, you can cuff the bottom of the denim and wear it in style with penny loafers.

But let’s break the rule for once here. Instead of cuffing the denim, leave it as it is but you need to make sure it doesn’t fully cover the penny loafers style.

Let’s go with a layering outfit here – Opt for White straight denim jeans and tuck in the t-shirt as a base layer. Add an overcoat or overshirt to layer up. 

Choose black, brown, beige, or navy. Finally, finish off the outfit with stylish penny loafers colored suede brown, light brown, dark brown, and black.

Add a few accessories to your outfit to enhance the style look. You can wear this outfit as streetwear, casual outing, or on any casual occasion.

Though straight-fit denim jeans will cover your penny loafers style, you can either cuff the bottom and show in style or you can break the rule and never mind about it. Still, it works.

Penny Loafers with Cuffed Chinos

Another way of styling the penny loafers is wearing them with cuffed chinos. Just like wearing cuffed pants, you can go to cuff the bottom of the chinos.

Moreover, you can stitch the cuffs on the cuffed chinos to permanently cuffs.

So, you don’t have to cuff every time you wear it. Usually, chinos are perfectly suited for semi-formal occasions where a professional outfit is not required.

You can opt black and white striped linen semi-formal shirt and pair it with white cuffed chinos then finish off the outfit with white penny loafers.

To make it more casual, you can untuck the shirt and walk with style. 

For occasions that don’t want you to be formal and any casual occasion, you can choose this penny loafer outfit.

Penny Loafers with Shorts

This is where penny loafers peaked. It doesn’t limit itself by matching it with suits, formal outfits, casual outfits, or any other. It also allows you to match the laid-back outfit.

Yes, the shorts, you can easily pair the penny loafers with chinos shorts to style.

In the transition from formal to casual to laid-back, you can blindfold and choose penny loafers to match shorts outfits.

Whether you are heading toward the yacht party, beach vacation, or any laid-back occasion, you can opt for a relaxed fit inner vest and laid-back fit casual shirt over it (unbuttoned). 

Then pair it with chinos shorts and finish off the outfit with penny loafers.

However, this outfit will give you a plain, something is incomplete feel. You can add a few men’s accessories to enhance and complete the penny loafers outfit.

Penny Loafers with Cropped Baggy Pants

We’ve viewed all the types of outfit styles. Let’s make the transition to the street style. 

If you want to wear penny loafers for a street-style outfit, you have to try different types of penny loafers. Have you ever heard of the Mix – Chunky Loafers and Penny Loafers?

Yes, Chunky loafers are a type of men’s loafers that can be worn for street-style outfits. And there is a mixed type of penny loafers and chunky loafers = Chunky Penny Loafers.

You can opt for it to style with cropped baggy pants. Let’s talk about the outfit.

Whether you are roaming the streets in style or simply traveling locally, opt for an oversized polo shirt with stripes or an oversized T-shirt and pair it with cropped baggy pants.

Normal fitted baggy pants for sure will cover your penny loafers style as a whole, so, opt for cropped on. Then finish off the outfit with Black Chunky Penny Loafers.

This outfit will give you a complete street-style appearance.

To make it more street style, you can add a few accessories like cross-body sling bags, bracelets, sporty watches, bold rings, and your choices.

Penny Loafers for Business Casual Outfits

So, you are heading towards the professional office space. Wearing the traditional formal wear, dress shirt, and khakis or dress trousers.

Apart from the usual footwear choice, you want to try something unusual that your colleagues never wore.

You can choose the penny loafers as they perfectly suit business casual occasions and professional office space. While dressing for the professional office space, try to hit the minimalist appearance. 

Choose a classic fit black dress shirt, pair it with grey striped or checked dress trousers, and finish off the outfit with black penny loafers.

This can be your go-to black penny loafer outfit. If you think checked or striped dress trousers are not familiar with your style, you can choose plain grey ones.

Make sure to wear socks when opting for penny loafers for a business casual outfit.

Penny Loafers for Smart Casual Outfits

Smart casual outfits where professional clothes aren’t required. 

More dress up than a tracksuit and less formal than a suit.

If you are dressing up for networking events, informal work social occasions, wedding receptions, or anywhere else, opt for a nice shirt. Probably white or powder blue.

Opt for a Black Blazer over it. Then pair it with classic-fit blue denim jeans. Finish off the outfit with brown penny loafers. And you are good to go.

Or you can choose a round neck T-shirt instead of a white shirt underneath. You can also play with colors like Tan, Navy, and more. Usually for this outfit, people choose leather sneakers.

When wearing the penny loafers, you are adding smart casual dress shoes to your outfit.

If you want to try a minimalist outfit, you can opt for a navy polo shirt paired with grey dress pants and finish off the outfit with black penny loafers.

Don’t forget about the fit, opt for slightly relaxed to feel comfy all day. And you aren’t required to wear socks, that’s your choice anyway.

Penny Loafers for Formal Wear

You are a professional employee. 

Wherever you see, people must have to wear formal outfits. In such scenarios, you have to be more professional and sophisticated to be more appealing. 

Penny loafers will allow you to style and showcase that you have a unique level of taste and are well aware of your appearance.

How about trying a few textured outfits? Opt for a crisp white dress shirt and wear a textured blazer over it. You can try a tan or navy blazer here.

Then pair it with tailored trousers or textured dress pants. Finish off the outfit with brown or tan suede leather loafers in style.

This can be your perfect formal wear for professional office space. Look out for the fit, and wear socks when you are wearing penny loafers with formal wear.

You can completely show off the penny loafer style with your colleagues and get compliments.

The Bottom Line

The Classic Penny loafers come straight from the 1960s and ruling the style game now. 

As you can see, your stylish dad and gentlemanly grandad used to wear penny loafers with unique flair. 

It continues to travel along with the fashion evolvement. So, you can incorporate it into your wardrobe and continue to style.

Do you like penny loafers for men? If so, Which penny loafer outfit will be your first to try? 

I would choose penny loafers for a tailor-made formal outfit with no socks.

How about you? Let me know in the comments, curious to hear from you.

Frequently Asked Questions (FAQs)