Four easy, default outfits guaranteed to get the job done. Without fail.

As the summer weather slackens and stiffens into the redding foliage of the fall season, it isn’t unusual to grow anxious for the chance to yank those autumn pieces out from the depths of your wardrobe. But the buzzing of the busy autumn months and the coming of cooler winds can also carry a vexing dilemma straight to your doorstep: the impasse of deciding what to wear.

If you’re looking to stop tearing out your hair and minimize the time you spend staring blankly into the shadows of your bedroom closet, here’s our guide to some failsafe combinations any guy can throw together and still look good. Before you know it, the winter will be here, so be sure to bust out these outfits while you still have the chance.

The Rebel With A Fashionable Cause

Harbingers of the nearing autumn surge always call for that third piece to break the seasonal gusts without overheating your body on warmer fall days. The Harrington jacket is masculine as it is versatile, obtainable in a spectrum of colours and modernized silhouettes. Both utilitarian and cool, you can snap the buttons open on this jacket to leave the collar out and show off a clean white tee underneath. Pairing this with some denim and Chelsea or combat boots will always give you that effortlessly uncouth flair of a young James Dean from Rebel Without A Cause.

KEY PIECES

Harrington Jacket, Naked and Famous Jeans, Chelsea Boots, Daniel Wellington Watch


The Simple Guy, Not the Basic Guy

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Fall weather is sweater weather: cozy sweater weather. Finding that perfect slouchy, shaggy pullover is the centrepiece of warmth and comfort when the season comes calling. Experiment with colours, stripes and necklines. To dress the look up, opt for wider legged pants or some cropped trousers for some sock action. Falling in line with the latest versatile trend, (read: Louis Vuitton, Vetements, Dior Homme) trousers and sneakers have taken over the runway and the street with their perfect marriage of business and casual. So finishing off the look with that pair of crisp, white leather sneakers every guy should have really pulls together that street smart look of the contemporary man. Incorporating a skullcap beanie can really edge up this outfit, but headwear is never a must.

KEY PIECES

Skullcap Beanie, Cozy Sweater, Cropped Trousers, Common Project B-Ball Low Sneakers

 

The Cool Guy Who Doesn’t Overdo It

The ancient adage that fashion fades but style remains will never cease to ring true for menswear. We know styles and trends recycle faster than Donald Trump’s golf cart drives. But we also know some items remain season-less. The biker jacket is the timeless garment every man should have in his wardrobe. And electing for a contrast berry-coloured dress shirt under a shrugged leather jacket gives you that pop of colour you need to squeeze in before the neutrality of winter style. Dark chinos, leather derby shoes and a handmade belt to marry the look together is a sure-fire way to look good at any time or place. Just leave the sunglasses at home.

 

KEY PIECES

Biker Jacket, Dress Shirt, Leather Belt, Dark Chinos, Dr. Martens Derbys
 

Drake Didn’t Invent This Mega-Cozy Number

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The shearling jacket is the esteemed ancestor of coats worn by fighter pilots back in the Second World War, naturally making it the ideal candidate for a marriage to some aviator sunglasses of the same hue. Its checkered history bargains a million combination possibilities, our favourite being slim-fit jeans and a pair of chestnut boots. The postwar staple’s contrasting textures offer a potential that can only be tapped with tactile layers underneath. Keep it modern with a denim shirt, or a clean white one joined by a wool scarf over top for some added sophistication.

KEY PIECES

Shearling Jacket, Aviator Sunglasses, Handmade Leather Belt, Brown Suede Boots