How To Dress Retro – Outfit Inspo When You’re A Guy

The golden era lives on if you can pull it off.

How To Dress Retro – Outfit Inspo When You’re A Guy

Accept it. What you’re wearing right now, and much of your current wardrobe, is born out of the last century. Hippies, punks, the military and nineties skaters – these subcultures have all returned as seasonal trends lately, making a comeback since their forties, fifties, sixties and seventies induction into menswear.

So, with all these bygone eras and bold fashion items on display, how can men navigate the world of retro fashion trends? What decades are dead? And what retro must-knows are happening in menswear right now? And which are here to stay? All will be answered and more if you read on.

Bowling Shirt With Trousers

According to Reece Crisp, menswear buying manager at Farfetch, the fifties and seventies are major trends this season. But, the retro trend, and the key items that come with these decades, is manifesting in a contemporary way.

“Think bowling shirts with cropped trousers, and shearling jackets styled with oversized sweatshirts and track pants,” says Crisp.

Retro Shirt With Modern Jacket

But, before you a grand ol’ vintage binge (or raid your grandpa’s closet), it’s important to work retro pieces with modern ones, and stick to your personal style guns – no imitations.

“Fuse the old with the new. It creates a more unique and individual look,” adds Crisp. “Keep it simple and don’t try to be someone else. Essentially, execute the look using key items that you are into.”

Leather Jacket With Jeans

The condition of the vintage-look item is super important. This includes things like the wash or colour of the item, as well as shape or silhouette and the fabric.

“Rocking brand new items, with really worn out vintage pieces is a don’t,” cautions Crisp. “Shape is also key. Silhouettes have changed dramatically, so it’s important that you bear in mind that even if the wash of the jean is right, you can get it very wrong with the fit.”

Lastly, making the choice to go authentic vintage – that is, an item actually worn and used in say, the seventies, can make all the difference. “Something like a biker or shearling jacket, I would go vintage every time. As perennial style pieces they age better and have more character as they do,” says Crisp.

Light Blue Jeans For Casual Wear

Collectively this season, vintage denim looks a lot like a light wash, blue pair of jeans in a straight-cut fit and a slightly high waist – much like the trouser. Channelling Americana workwear, look to something like the Levi’s 501 jean, roomier in the seat and tapered from the knee down for a contemporary fit.

“Light blue jeans are a men’s staple,” says Crisp. “Wear them with everything, except maybe with tailoring such as a formal blazer.”

Shearling Bomber Jacket For Colder Months

If you only buy one jacket this year, make it a shearling bomber. Steeped in early-last-century aviation and seventies cool, you don’t have to go the whole way with the sheep skin feel. Shearling, especially in not so hot climates, is most versatile as a collar trim on leather bomber jacket.

In true winter chill, invest in a fully-lined one, keep you feeling warm and looking cool. The beauty of a shearling jacket is that it’s a statement in its own right. Just add a t-shirt, jeans and clean cut sneakers. Or, as Crisp insists on wearing the jacket, keep in authentically retro and bold: “Go Rocky-style.”

Turtleneck Sweater With A Coat

Also known as a turtleneck or skivvy, the rollneck sweater is one of the most polarising retro fashion items to return to the contemporary menswear market. But, it packs a punch when worn correctly, considering not many guys can or want to pull it off.

Rock it under a suit jacket or overcoat in winter. “Or style it under a check shirt, and a suede Harrington,” says Crisp. “Get those textures going.”

Revere Collar Shirt For Warmer Months


One of the biggest summer must-haves, the revere collar shirt is the perfect way to inject some Frank Sinatra-goes-on-vacay into your personal style, without the need for a straw fedora.

Look for bold vintage prints in faded colours (sun-beaten is more subtle) and wear the Cuban-feel shirt with tailored chino shorts and espadrilles or linen trousers and loafers for a smarter feel. It’s a great layering piece worn open over a singlet or t-shirt. And for a streetwear vibe, “style it over a long sleeve tee.” Add some nineties kicks and tapered track pants.

Peak Lapel Jacket For Formal Occasions


In the twenties and thirties, the peak lapel ‘peaked’ on many single-breasted suit and dinner jackets. But nowadays, the flare-ish lapel is more common as double-breasted blazer, adding to the jacket’s expansive line, and thus, broadening the shoulders. Practicalities aside, it’s a statement lapel that ripped up smart casual style at Pitti Uomo’s most recent edition, and isn’t ‘peaking’ anytime soon.

“Go classic with a twist,” says Crisp. “Team with a granddad collar shirt.” Footwear? Chunky sole derbies or simple leather sand shoes.

Short Swim Trunks For Swimming


Swim shorts offer a mix of fun and practical this season. Just like the spring racing carnival, your swimmers should embrace colour and print as a way of standing out from the beach crowd and celebrating summer. And if you’ve got the confidence to do so, trunk styles are going shorter (but not tighter) too, this season. But within reason.

“The short retro trunks are only ok at the beach,” says Crisp. And, keep the retro boat afloat with a vintage top to match. “Style with a towelling tee.”

White Sneakers With Jeans

The white sneaker isn’t new. But it’s the ultimate blast-from-the-past shoe and is going even more vintage this season with canvas-leather models kicking up the scene and a plethora of heritage brands reintroducing classic sneaker silhouettes.

“For the white sneaker, keep styling retro,” says Crisp. “Opt for slim jeans, a polo shirt and a biker or bomber jacket.” Super neat, retro chic.