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A Case for Wearing Loafers In Winter

January 12th, 2022

Because, why not?

Today we welcome a new contributor to the site, Mr. Casper Lundmose. We’ve long been a fan of the excellent taste he displays on his Instagram account and we’re pleased introduce his voice to our audience here. Give him a warm welcome! –HSS

As we have entered the more chilly and darker months, many of us in the menswear world are welcoming the opportunity to bundle up: layering, Barbour jackets, and turtlenecks, oh my!

As a result, many also see it as a natural transition to stow away the trusty summer-loafers. I do, however, find that it is a total misconception that loafers are to be worn exclusively during the spring and summer. Why not wear loafers in the winter too?!

wearing loafers in winter

I enjoy wearing my pennies and tassels all year round and find them just as at home with heavy flannel or jeans and woolen socks, as with linen trousers, shorts, and no socks. (Yes, you heard me right: no socks!)

Made to do the dirty work…

First off, a little background story. I reckon that you probably know the history of how the Penny Loafer got its name; how the preppy Ivy Leaguers used the cut-outs on the saddle across the upper part to hold a penny to use in a phone booth (a concept very hard to explain to our youth today by the way). This was around the 1950s and 60s.

wearing loafers winter

However, taking a step further back, the design actually originates from early 1930s Norway, where Nils Tveranger introduced the Aurland shoe made for Norwegian fishermen and farmers. (Norwegian fisherman and farmers got the Aurland shoe and the Irish fisherman and farmers got the Aran sweater.) These comfortable slip-ons were made to be able to do both the “dirty work” as well as be used when off duty.

Versatility is key…

I am a firm believer that if something was originally made with a purpose in mind, we should be true to the original idea and it should be used for said purpose. For instance, that’s the same reason why I take my 30-year-old Tag Heuer 1000 swimming and why I still carry a pocketknife as an everyday essential.

| CASPER’S EDC | Vintage Tag Heuer 1000, Victorinox Swiss Army Knife

Now, yes, I wear my loafers all year round, but naturally the often more rainy and chilly weather rules out some of them. For example, I obviously wouldn’t wear my leather-soled, tan suede penny loafers on a rainy day–that’s a given. And my drivers doesn’t work either.

But the classics like the Penny, the Tassels, and so on, will do the job perfectly.

READ MORE: The Definitive List of Men’s Loafer Styles

Go full leather with a rubber sole and you are good to go as well in the summer, as in winter (and spring and fall for that matter); something like the G.H. Bass Weejun. It was the original, so why not opt for the original that is still so true to its roots.

wearing loafers winter

Or for something a little different, the Charles Penny Loafer from Brugnoli in Rome. I own a pair in dark brown suede with a crepe rubber sole that you might recognize from the Desert Boots, which making them extremely comfortable, durable, and versatile.

Made to be worn at all times, so wear them at all times! (Well, almost anyway.) But, you can wear loafers in the winter. For sure.

Thanks for reading.

Stylishly Yours,

Casper Lundmose
He Spoke Style

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Casper Lundmose

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If you're in need of a little winter outfit inspiration, you've come to the right place. Whether you're dressing casually, in need of something for an evening out, or want to try something new, I've put together five of my best winter outfit ideas to help you out.

One of the things I always think is tough when it comes to winter outfits is dealing with outerwear. How many times have you built a great look around a piece of outerwear only to have it feel incomplete when said piece of outwear is removed? It's a common occurrence this time of year. That's why I fully endorse the sweater layered over button-up look. It's practical, stylish, and looks complete and completely unfussy even without a coat.