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Trending 5 May 2023

How to Style your Bomber Jacket this Season

A bomber jacket is the perfect piece of outerwear to complete any look and is the most stylish purchase of the season.

Did you know that Bomber jackets were originally designed to keep pilots warm in the cockpit during World War I? They've certainly been through an evolution since. With so many versions of the trending bomber jacket available, there is sure to be one out there that suits your style and taste. We have rounded up some brilliant looks for men's bomber jackets for any occasion, whether it's a sleek, sporty look, a bold streetwear look or a night out look.

Words By Erin Visagie

Ala Tyler the Creator

For the perfect streetwear bomber jacket look inspiration, look to Tyler the Creator, one of the coolest guys in the business. Now that the varsity bomber jacket has returned, the prepped-up version of the bomber can also earn you plenty of style points on the streets. Choose the CHOCOLATE logo-patch varsity jacket for a cool weekend look.

Take your weekend in stride with a minimalistic tee-shirt like this Off-White logo-print cotton sweatshirt; Off-White is known for its awesome streetwear, particularly for combining pop art references and punchy graphics. A unique diagonal stripe print is featured on the sleeves for instant cool factor, and the crisp white colour creates a balance between relaxed and polished.

Combine it with some cute midrise straight-leg trousers; you can’t go wrong with these affordable black Nike midrise straight-leg trousers; they’re super flattering and super comfortable, made out of cotton, have pockets, and still possess the awesome Nike cool factor.

Jordans always look good; a fresh and timeless addition to any wardrobe, the iconic Air Jordan 1 Mid sneaker is a great option; with its bold red, black and white design and signature silhouette, these shoes are exceptionally cool, and you can wear them with almost any outfit, so it’s a great investment.

You can finish off your look with this excellent Supreme logo print shoulder bag. It’s bold, great for days out or nights out, and it features adjustable fastenings and a zipper closure.

:CHOCOOLATE Logo-Patch Varsity Jacket, $267, Farfetch

Timothée Chalamet-esque

We suggest giving the ASOS DESIGN faux fur hooded bomber jacket in black and white letter print a try. It’s perfect for standing out and staying warm with its edgy print, hood, and side pockets. Plus, it’s super easy to style.

To complete your look, we recommend adding an edgy knit like the Jaded London knitted star singlet in black. The cool star in the middle of the knit adds to its edgy and bold feel, and it’s got a crew neck look and sleeveless style for an effortlessly cool look. It’s reminiscent of a Timothee Chalamet kind of look!

And last but not least, add a pair of Boohoo Elastic Waist Slim Fit Buckle Cargo Joggers to your outfit. These will give you extra style points, are cost-effective, and look polished yet edgy.

Accessories-wise, for an eboy look, pair a cool ear cuff or a fabulous chain necklace. The Tom Wood Sterling silver cuff, this ear cuff has a relaxed incomplete circle shape; it’s polished and captures an air of coolness that adds to this look. If you like a chain look, the Emanuele Bicocchi sterling-silver necklace is for you; it has a rebellious edge, a cool engraved skull and pearl charms on a cool chain, and it’s minimalistic but bold all at once.

ASOS DESIGN Faux Fur Hooded Bomber Jacket in Black and White Letter Print, $168, ASOS

Office Attire 101

For a polished, timeless look perfect for your office attire, pair your bomber jacket with a dress shirt.

You’ll love the ASOS DESIGN extreme oversized bomber jacket with MA1 pocket in brown; it’s trendy, great for layering, has pockets, and a cute oversized fit. Plus it’s super professional at a low price and has a cool baseball collar. Is there anything not to love about this?

Make it work-appropriate by pairing it with a white dress shirt. This Levi’s relaxed fit western shirt is made from cotton-hemp denim, features dual front pockets, long sleeves, and a contemporary, relaxed fit. Wear this piece for years to come and pass it down to future generations with its durable denim and timeless style.

Put on a pair of Pop Trading Company Hewitt Suit seersucker tailored trousers to add extra polish to the look. The trousers are tailored with a high-waisted fit that’s flattering, plus they’ve been embroidered with a cute logo on the legs. A belt with a polished buckle like the Chestnut brown calf leather belt from R.M. Williams can elevate your office look.

Put your best foot forward with the Brown Truro Loafers from Manolo Blahnik. Handcrafted and fancy, they have supple suede uppers and smooth leather linings, and they’re minimal and smart.

ASOS DESIGN Extreme Oversized Bomber Jacket with MA1 Pocket in Brown, $136, ASOS

We're Going Out

For a more edgy but cool night-out look, start by wearing the ultimate leather bomber jacket, such as the River Island PU bomber jacket in black. With its cool collar, functional pockets, and super cool faux leather effect, this leather bomber is the ultimate jacket upgrade.

Wear this with a basketball-patterned tee or any graphic tee of your choice. Our recommendation for this look is the New Era Chicago White Sox heritage t-shirt; even though it pays homage to baseball, it’s still a cute wardrobe staple.

Dress up your night-out wardrobe with these Tommy Hilfiger 1985 Bleecker Pima Cotton Chinos, made from mixed organic cotton with added stretch for a perfectly dressy yet casual look.

Rathdowne Wild Rhino shoes mix a high-top with a cute sneaker, making them the perfect footwear. With contrasting colors and materials, they are made from premium Portuguese leather, and are comfortable and supportive while looking great.

River Island PU Bomber Jacket in Black, $126, ASOS

Monochromatic Masc

The Frankie Shop’s Evans Bomber jacket captures a cool minimalistic look with its refined feel, fits a contemporary aesthetic, and, in pale green, it’s classic but with a twist. It’s made from technical twill with a satin lining.

There’s no doubt that cargo pants are super trendy right now, and The Frankie Shop’s Grant flap-pocket twill cargo trousers bring back utilitarian looks with a modern feel. In addition, these look great paired with the bomber jacket above.

There Was One’s crew-neck cashmere jumper is a great choice for layering. The timeless crew neck silhouette and soft regenerated cashmere make this sweater versatile, minimalistic, and warm.

Your look will be more put together if you carry a crossbody bag like the ASOS DESIGN faux leather crossbody camera bag in ecru.

We recommend pairing the Stepney Workers Club Pearl S-Strike low-top sneakers to complete your look. These sneakers are a perfect balance of classic and trendy, and they will undoubtedly make you stand out in any crowd.

The Frankie Shop Evans Twill Bomber Jacket, $360, Matchesfashion