What to wear with this season’s must-have Penny Loafers? 

Our focus has shifted in recent years away from street style and athleisure-inspired pieces to a more understated but effortless wardrobe. A mix of soft tailoring, versatile layers and classic silhouettes that feed effortlessly into your already existing wardrobe. 

With that said one footwear trend that is worth investing in this season is the penny loafer, originating in the 1930s, these versatile slip-on shoes have had a major resurgence, providing the style-conscious with a shoe that can be styled for every occasion. Today we are looking at what to wear with the penny loafer

Mens loafers


Legend has it that in the 1930s, students at Ivy League universities would slip a penny into the diamond-shaped cutout on the vamp of their loafers as a fashion statement. This playful touch was the start of the “penny loafer.”

The iconic design, characterized by a moccasin-like construction with a saddle-shaped strip of leather across the instep, has remained largely unchanged over the years. Renowned for their clean lines and minimalist aesthetic, the absence of laces adds to their overall sleek appearance. Often associated with a smarter wardrobe, they have become very much a go-to everyday shoe. 

  1. Classic Knitwear 

As we head into autumn/winter, it’s nice to incorporate more textured pieces into your wardrobe. Pair a mohair knit or brushed cardigan with the swingy bag trousers that are another trend that isn’t going anywhere. This provides you with a versatile outfit for weekend and workwear. 

  1. Layering Essentials 

You need those kinds of staples that you can throw on for any occasion, no matter what the weather, it won’t compromise your style. Trench coats, bomber jackets and denim styles are key silhouettes this season paired with chunky soft accessories. 

  1. Smart Casual 

Invest in wardrobe pieces that are versatile no matter what day of the week it is or the occasion. The penny loafer adds that zest to a causal outfit balancing it with a more refined footwear choice in comparison to a trainer. 

The resurgence of penny loafers is a testament to their classic design. Invest in a pair of loafers and we promise, you will enjoy them for years to come. With their versatile style and unmatched comfort, they have firmly established themselves as a ‘must-have’ so get ahead of the curve and start styling yours for this season. 


All questions asked with Max Svärdh and Albin Johansson | Axel Arigato


All questions asked with Max Svärdh and Albin Johansson | Axel Arigato

We join the duo behind the Swedish powerhouse Axel Arigato. Renowned for its minimal trainers, relaxed streetwear and community-driven business model, here's everything you need to know about the cult brand...

2022-08-31 10:16:35By Holly Thompson

Holly Thompson

Holly Thompson

Writer and expert