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  • July 03, 2023 3 min read

    Long misunderstood as 'the perfect summer shoe,' loafers are arguably the most versatile shoes available and the penny loafer, in particular, is the perfect style to carry one through the cooler months. 


    Australian winters are relatively moderate compared to the harsh winters experienced in some parts of the Northern Hemisphere.

    A pair of Goodyear welted, calfskin penny loafers, such as the Bourke pictured below, can be worn with perfect utility through the autumn and winter months in Australia, which isn't necessarily the case in some parts of the U.S. and Europe. 


    There are, of course, a few things to consider when wearing penny loafers in winter. Firstly, darker colours will work with a lot more outfits. Secondly, when it rains, darker colours conceal water spotting or damage much better than lighter colours, such as light brown.

    To protect your leather shoes on rainy days, we recommend using water resistance spray prior to leaving your home. Rubber topy's are a good option too.  If you experience high rainfall, a rubber overshoe, called a "galosh" might be helpful.

    Waterproof your loafers


    Another consideration: socks or bare ankles? Logic would suggest wearing socks on colder days, indeed convention requires it.

    However, this really depends on where you live. Wearing 'no-show' socks on a warm Autumn's day in Brisbane would be perfectly acceptable for a casual outing.

    For more formal occasions, preference should be for socks and a standard trouser length with a clean taper at the base and no break over the shoe. Cropped trousers or no shows are for less formal gigs. 

    Socks Or No Shows - Let Weather Decide


    If you have your penny loafers stored away, get them out this instant! 
    One of the penny loafers' talents is their extraordinary versatility. They can fit out an entire wardrobe with ease and will lift almost any casual ensemble you own. 

    Black Leather Jacket

    The black leather jacket and black jean / chino combo is already a stylish look. This relaxed combo can be taken in a more sophisticated direction by pairing them with black penny loafers. This look also looks great with a black V-neck or grey henley tee. 



    Few items of clothing can lift one's gravitas and maturity like the turtleneck. If one's raison d’être is this end, then there is no better companion than the penny loafer.

    Woolen pants or grey chinos work exceedingly well with turtlenecks. For more interesting and modern-looking casual ensembles, penny loafers can breathe extra elegance into that look, as we see below. 



    As a stylish minimal shoe, the penny loafer is perfectly at home with a well-fitted suit. As a rule of formality, some may disagree. They probably don't wear RMW boots with their suits either.  

    Black penny loafers can work well with black, navy, charcoal or light grey suits. Brown can certainly be worn around town in a navy or light grey suit.

    For around the office, consider a shade of sock similar to your pants.


    Tweed Blazer and/or Fair Isle Knitwear

    Tweed is synonymous with sports jacket and a popular choice in autumn and winter due to its thickness.

    There are many wears to pair tweed and penny loafers are an excellent partner. Black penny loafers pair smartly with grey tweed and black trousers. Brown penny loaders work very well with brown tweed and grey/beige pants.

    Adding fiar isle knitwear into the mix (or pair it on its own) sets the whole ensemble on fire. 

    Further Reading

    Information Guide: The Penny Loafer

    5 Reasons Why Every Man Should Own Penny Loafers

    Image References

    Jeff Lack -  Stylist, Editor, Content Creator, Mentor | Website | Instagram

    Lookastic - Virtual lookbook all things menswear | Website | Instagram

    Jared Acquaro - Brand builder, men's style writer, cobbler | Website | Instagram - Premium online men's style content | Website | Instagram

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