Introduction

Footwear is a key component of successful winter style (and style in general, actually.) Ill-considered and less-than-appropriate shoes can – and will – make you look a little ridiculous on all counts. A parka married to a pair of espadrilles, a crime I’ve witnessed on more than one occasion recently, is an outfit employed by the least of sartorially fluent.

Today’s article is going to be taking a look at a somewhat grey area when it comes to autumn/winter footwear – the loafer. For some, the loafer is seen strictly as a spring/summer option. While for others, loafers are an acceptable choice all year round, transcending seasons and earning their place within a contemporary capsule wardrobe.

How to Wear: Loafers In Autumn/Winter

To avoid looking like a seasonal mismatch, it’s a safe bet that you’re going to need to wear socks with your loafers in the winter. This will not only make them a much more practical option in the cold weather but brings about an opportunity to express your individual style.

A good pair of wool socks with a cable or heritage inspired design adds an air of weather-awareness to your outfit, as they glimpse out between the loafer and trouser break. A thicker gauge than you would utilise in summer also removes the practicality issue of winter-worn loafers.

The climate will also dictate your loafer wearing habits. Certain styles – i.e. driving shoes, suede and slippers – will not fair well in the wet, slush and snow so choose your style of loafer with caution and thought.

Men’s Autumn/Winter Loafers Lookbook

Although some of the outfits in the lookbook below feature no socks, they are an easy addition and will allow you to effortlessly individualise your own look. Whether you opt for a textured pair to add another dimension or simply complement or contrast with your sock colour, you can choose to make as much or as little of a statement as you desire:

Men's Autumn/Winter Loafers Lookbook

Look One

A pair of leather tassel loafers, paired with woollen burgundy socks and raw denim jeans, creates a bottom half suitable for colder conditions. The slight heel in the loafer makes them more practical than drivers on damper days but a good pair of hiking or duck boots would be even more than suitable substitutes in this outfit.

A white shirt with a neutral, thick knit crew-neck jumper and an ever-essential pea coat layered over the top stylishly finish off this everyday look:

  • Topman Peter Werth White Poplin ShirtTopman Peter Werth White Poplin Shirt
  • Easy Mixed Yarn JumperEasy Mixed Yarn Jumper
  • Allsaints Frith Pea CoatAllsaints Frith Pea Coat
  • Levis Broken Raw Rinse 510 Skinny JeansLevis Broken Raw Rinse 510 Skinny Jeans
  • Falke Airport Merino Wool-blend SocksFalke Airport Merino Wool-blend Socks
  • Kg By Kurt Geiger Arden Washed LoafersKg By Kurt Geiger Arden Washed Loafers
Look Two

This season, like the last, will favour looks that combine loafers and suits for a continental take on tailoring. Leave the no-show socks at home and opt for some trouser-matching socks to keep your feet warm and your outfit fluid.

Brown penny loafers paired with a two-button navy suit is both timeless and sartorially savvy. A roll neck jumper remains on trend for the season and looks great as a shirt and tie substitute, especially as the weather worsens. All the while, a brown leather briefcase has you looking like you mean business:

  • Allsaints Link Roll Neck JumperAllsaints Link Roll Neck Jumper
  • Reiss Andrews Single Breasted Peak Lapel Suit Mid BlueReiss Andrews Single Breasted Peak Lapel Suit Mid Blue
  • Austin Reed 110 Silver PaisleyAustin Reed 110 Silver Paisley
  • Mulberry Elkington Leather BriefcaseMulberry Elkington Leather Briefcase
  • 3 Pack Of Navy Jeff Banks Socks3 Pack Of Navy Jeff Banks Socks
  • Churchs Leather Penny LoafersChurchs Leather Penny Loafers
Look Three

For the days when the weather relents, it’s still a viable option to go sockless. However, tread with caution; leave any heavy-duty outerwear at home so as not to strike an unbalanced contrast.

A jumper should be enough to keep you suitably warm if you’re able to leave the socks at home (or have gone for invisible socks). Animal Motifs have had a fairly big presence this year within the industry and a statement piece of knitwear is one of the easiest ways to rock this particular trend. Keep everything else toned down, naturally, with some deep green trousers and grey tassel styled loafers:

  • Aubin & Wills Welimeadow Fox Intarsia Merino Wool SweaterAubin & Wills Welimeadow Fox Intarsia Merino Wool Sweater
  • Reiss Senator Slim Fit Casual Trousers GreenReiss Senator Slim Fit Casual Trousers Green
  • Topman Miller Herringbone Slim Soled LoafersTopman Miller Herringbone Slim Soled Loafers
Look Four

While driving shoes aren’t the ideal candidates for when the weather is wet and the floor is damp, they are still a viable option when all is dry. The ‘open’ nature of drivers allows you to add a pop of colour to your look with some coloured or equally printed socks. Alternatively, if you want to keep your sock choice slightly more subtle, tie the colour of your socks to the top half of your outfit.

A grey pair of chinos goes with everything; effortless and easy to wear, they will anchor the pop of colour you’ll get from the driving shoe and sock combination. A white t-shirt and navy blazer keep the look smart-casual while a scarf will go some way to fending off the winter chill:

  • River Island T-shirtRiver Island T-shirt
  • Reiss Shore 2button Patch Pocket Blazer NavyReiss Shore 2button Patch Pocket Blazer Navy
  • Dockers Gravel D Zero S TrousersDockers Gravel D Zero S Trousers
  • Paul Smith Accessories Navy All Over Polka Silk Dress ScarfPaul Smith Accessories Navy All Over Polka Silk Dress Scarf
  • Topman Monochrome Spot 5 Pack SocksTopman Monochrome Spot 5 Pack Socks
  • Car Shoe Leather Driving ShoesCar Shoe Leather Driving Shoes
Men’s Loafers
  • Loake Suede Tassel LoafersLoake Suede Tassel Loafers
  • Topman Miller Suede Slim Soled LoafersTopman Miller Suede Slim Soled Loafers
  • Asos Penny Loafers In LeatherAsos Penny Loafers In Leather
  • Reiss Brunswick Smart Loafers BlackReiss Brunswick Smart Loafers Black
  • Topman Venice Penny LoaferTopman Venice Penny Loafer
  • H By Hudson Tyska Brown Suede ShoesH By Hudson Tyska Brown Suede Shoes
  • Ask The Missus Malibu Kiltie Loafer Navy NubuckAsk The Missus Malibu Kiltie Loafer Navy Nubuck
  • Bass Weejun Burgundy Layton Tassel LoafersBass Weejun Burgundy Layton Tassel Loafers
  • Tods Suede Moccasin Loafers 134264Tods Suede Moccasin Loafers 134264
  • Paul Smith Shoes & Accessories Leather Penny LoafersPaul Smith Shoes & Accessories Leather Penny Loafers
  • John Lobb Truro Leather Tassel LoafersJohn Lobb Truro Leather Tassel Loafers
  • Mr Hare Mens Wilde Loafer ShoeMr Hare Mens Wilde Loafer Shoe
Conclusion

As the mornings get colder and the sun becomes increasingly fleeting, most of us are found making more winter-weather appropriate wardrobe choices. From perfectly practiced layering to on-point outerwear, everything is to be considered when putting together a stylish autumn/winter look.

The loafer has become a footwear style that is able to transcend seasons and appropriate in all but the worst of weather conditions. But what do you think?

  • Is the loafer only suited to spring/summer when you can go sockless?
  • Do you currently own any loafers? If so, what styles?
  • How do you like to wear your loafers in autumn/winter?
  • Are any of you still going sockless in this weather!?

Let me know in the comments section.