How To Experiment With The Oversized Look

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How To Experiment With The Oversized Look

Words by Mr Derek Guy

28 March 2024

illustration by Mr Jean Michel

01. Baggy sweaters

Shortly after photos of Simons’ AW16 runway show hit the internet, some of the items that caught the most attention were the tennis sweaters, V-necks and cardigans. This is partly because an oversized silhouette is easier to wear in the form of knitwear. Baggy sweaters are charming, as they suggest comfort and ease. The simplest way to experiment with a looser silhouette is therefore to size up your knitwear.

When shopping, consider the placement of the hems and shoulder seams. Mr Haider Ackermann is famous for his droopy, oversized sweatshirts with off-the-bone shoulder seams and overly long sleeves that stack just above the wearer’s wrists. But since the sweatshirts are slightly cropped, they look intentional rather than sloppy.

Similarly, Mr Billy Crystal’s iconic cream-colored Aran in the 1989 film When Harry Met Sally… is just as charming for its generous volume as it is for its thick cables. The shoulder seam falls a few inches off his shoulder bone, but since the banded hem is tucked up under the sweater, everything looks tidy.

When trying on an oversized knit, consider the sweater’s overall shape. Comfort doesn’t have to come at the expense of appearance if the hem can be adjusted so it sits higher on your body.

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02. Wide-legged trousers

Men who grew up in the 1980s and 1990s may be reluctant to slip back into wider trousers, as they remember the frumpy Dockers they wore to their first service job. Or the giant JNCO jeans they wish they could forget. Ironically, many Gen Xers and Millennials associate slim-fit with youth, but Gen Z has been at the forefront of pushing for wider silhouettes, partly because they associate slim, low-rise pants with their parents.

Don’t get hung up on leg width – pay attention to the trousers’ overall shape. Wide-leg trousers can drape beautifully if they have a high waist and fall in a pin-straight line, ideally made with knife-edge pleats.

LEMAIRE also makes “twisted leg” trousers, where the outseam pulls the side of the trousers on top of the centre of the shoe, creating a balloon-shaped silhouette. RRL has cargo pants with adjustable ties at the cuffs, allowing you to cinch the leg opening to create a more interesting shape.

When it comes to buying wider trousers, it’s all about paying attention to the overall silhouette, not just volume. This will help you push these away from shapeless Dockers territory.

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03. Raglan-sleeved topcoat

In 2015, Ms Cathy Horyn wrote a persuasive article for The New York Times on the “post-trend universe,” where “there is no single trend that demands our attention, much less our allegiance, as so many options are available to us at once”. Today, menswear is Balkanised into tiny islands oriented around tailoring, streetwear, workwear, patchwork shabby chic and the avant garde. One thing unites these disparate communities: the beloved oversized topcoat.

A big topcoat can be worn with everything from baggy sweatshirts and jeans to chunky fisherman knits paired with grey flannel trousers. Teamed with a fuzzy mohair sweater and some wide-legged, self-belted trousers and you have something that looks more contemporary.

The key is to get something with raglan sleeves. The term “raglan” refers to when a sleeve seam slants from the neck to the armpit. According to legend, the style originated during the Crimean War, when Lord Raglan’s troops were so cold that they cut holes into blankets and slipped them over their heads. A raglan construction differs from what’s known as a “set-in sleeve”, which sort of looks like what you see on dress shirts or T-shirts.

One of the advantages of a raglan is that, without the vertical seam seen on a set-in sleeve, it’s easier to layer the coat over other things (useful when the coat is oversized). Get something voluminous that comes down to your knees. You want something that swishes when you walk and conveys a sense of drama.

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04. Consider your aesthetic

It’s easier to incorporate a fuller silhouette into some aesthetics than others. Over the course of his career at Dior, SAINT LAURENT and now CELINE HOMME, Mr Hedi Slimane’s collections have been defined by their skin-tight, bone-hugging clothes. It would be difficult to achieve that teen rocker look with something looser, but some aesthetics almost cry out for fuller-fitting items.

Take workwear, for example. From the French labourers who wore the bleu de travail to American foresters who braved the cold in Filson’s Mackinaw wool jacket, work clothes have always been looser to accommodate freer and more comfortable movement. You will never look wrong in a pair of fuller-fitting OG-107 fatigues, a chambray work shirt or a Melton wool duffle coat.

Similarly, a lot of streetwear nowadays takes inspiration from the 1990s, when young men in coastal US cities flipped preppy Ralph Lauren clothes to create an aesthetic all their own. Baggy jeans met with oversized, block-coloured sportswear, Polo Bear sweaters, striped rugby shirts and choice pieces from Ralph Lauren’s Stadium and P-Wing collections. Brands such as Aimé Leon Dore have obliquely referenced this vibe in the past few years, propelling them to success.

When considering an oversized silhouette, think about the aesthetic you’re trying to create. A fuller-fitting, Oxford-cloth button-down shirt can look charming with wide-legged chinos in the right context, but the uniform can also recall the worst of 1990s business dress. Wear the same shirt with olive fatigues and you’ll bring it back to workwear. Similarly, an oversized sweater with double-knee painter pants and sneakers will feel very natural, as it recalls some of that 1990s streetwear style.

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05. Consider proportions

Finally, consider the proportions of your outfit. Over the past 20 years, men’s clothes have shrunk all over – slimmed-up, short jackets have been worn with tight, low-rise trousers and slim shirts made with diminutive collars. This makes sense: when you shrink the proportions of one item, you often need to shrink everything else in tandem. Similarly, an oversized, raglan-sleeved topcoat can be teamed with wide-legged trousers and chunky boots, reversing everything that has been done in the past two decades. In this way, the overall silhouette is looser, but everything looks harmonious and balanced.

Conversely, you can also play with the proportions of your outfit by pairing a slimmer sweater with wider-legged trousers or wearing a voluminous, rounded bomber with slim-straight jeans. Sometimes, a wide-legged trouser calls for a chunky boot underneath to fill the volume around the hem. Other times, you want to wear a dainty, soft-soled loafer to play with the tension between these two shapes and call attention to the wider silhouette.

When you start to stray away from moderate, classic silhouettes, you will need to figure out what works for you. Pay attention to the horizontal lines of your outfit – where the waist is nipped, hemlines fall and trouser cuffs hit. Belts and drawcords, the transitions between different items, layered hemlines and cropped trousers can help segment your outfit into blocks, creating visual interest and more flattering proportions, even if you’re wearing oversized pieces.

The most important tip: if something oversized doesn’t feel like it’s working for you, consider whether you’re just wearing it with the wrong things. You can feel like you’re swimming in an oversized balmacaan if you only wear it over a dress shirt. But layer a chunky Aran underneath to help fill up that volume and you’ll balance the coat’s visual weight with your knitwear.

When the pieces lock in, trust us, you’ll understand why everyone has been talking about the charm of fuller-fitting silhouettes.

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