How To Wear Every Fit Of Jeans

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At the risk of sounding like the failed musician turned guitar teacher who taught you to play Smoke On The Water when you were thirteen, you don’t become a rockstar without first brushing up on your rudiments.

The same is true in menswear, and one of the chords it’s always worth brushing up on is how to wear your favourite fit of jeans. It’s one of the basics, like knowing what shoes to wear with your suit, or the subtle nuances that differentiate an Oxford from a Derby shoe.

Don’t underestimate it. The best jeans in the world are the ones that fit you. So it pays to know the different cuts of jeans available, the body types they suit and what looks best with them. From wide-leg denim to your favourite skinny jeans, these are the dos and don’ts of wearing every fit that matters.

Skinny Fit Jeans

River Island

Surely the most polarising cut in the world of jeans, skinny fits may have disappeared from the runways, but all it takes is a stroll around town to see that this nut-hugging style is still abundantly popular outside of high fashion.

In the interest of balance, it’s important not to wear them with anything too loose, baggy or bulky. “Avoid wearing your chunky trainers with skinny jeans,” says stylist Sarah Gilfillan, founder of men’s personal shopping service SartoriaLab.

It’s also worth taking the shape of your legs into consideration before squeezing yourself into a pair. “Anyone with a chunky build should give skinny-fit jeans a wide berth,” says Gilfillan. “The shape will accentuate the width of your legs in a non-flattering way.”

In other words, unless you’re deliberately trying to show off your leg-day #gainz a la Jersey Shore (not recommended), this is probably something to avoid.

What To Wear With Skinny Jeans

Contrary to what menswear purists will tell you, if you’ve got the pins to pull them off, skinny jeans can still look good. The key is to complement them with similarly slim-fitting footwear and wear with an appropriate dose of rock ‘n’ roll attitude.

“This fit looks great with Chelsea boots,” suggests Gilfillan. “Or, for something more casual, try trainers with a fairly slim sole, like Converse or Vans.”

If you opt to go down the Chelsea boot route, we’d recommend pairing grey or black denim with black leather footwear. Throw on a white tee for contrast and then tie things together in true rockstar fashion with the addition of a leather biker jacket.

Slim-Fit Jeans

Jack Wills

The gift that keeps on giving. There are only a handful of fits that seem to remain stylish season after season, year after year, and this is one of them. The gift that keeps on giving.

Slim-fit jeans have the benefit of complementing a wide range of body types and outfit choices. They work on lazy T-shirt days and also ground more complicated looks that involve layering or tailored pieces. Men’s luxury personal shopping guru Daniel Johnson has only one caveat.

“Slim-fit jeans are versatile but perhaps not the first choice if you happen to be carrying a little extra weight on your thighs or have a larger stomach,” he says.

Generally speaking, though, whether you’re more like Jeff Goldblum or Kevin Hart in the height department, a pair of slim jeans will see you right.

What To Wear With Slim Jeans

To repeat, one of slim-fit denim’s major draws is its versatility. This is a cut you can easily incorporate into anything from a smart-casual get-up for a job interview to something more laid-back for hitting a bar come Saturday night.

“Footwear wise, brogues, lace-ups or loafers are a good option for smart casual,” suggests Johnson. “Just steer clear of bulky boots, which can look out of place.”

To keep things strictly casual, raw denim and white canvas high-tops will always be a match made in style heaven. Team them up with a patterned T-shirt to add a focal point and then slip into an overshirt or light jacket to keep the chill at bay in style.

Wide-Leg Jeans

Zara

Wide leg jeans are yet another 90s trend to have strutted back into our lives via the catwalk, for better or worse. Unlike wraparound shades or tie-dye tops however, they’re one that can have some positive effects on your wardrobe when styled with a little thought. So before you write them off as just another high-fashion fad, consider the following.

The wide shape of this cut can work to flatter broader builds. “It’s ideal for anyone looking to balance out wide shoulders, chest or calves,” says Johnson.

Where slim or skinny fits will only draw attention to love handles or chunky legs, wide-leg jeans will soften them, creating a clean, straight silhouette from top to bottom.

That’s not good for every body type, however. “If you’re a skinny guy with slim legs, wide-leg jeans are not for you,” says Johnson.

What To Wear With Wide-Leg Jeans

The key to sartorial success with wide-leg dad jeans is to ensure the rest of your outfit is in keeping with that easy street spirit. Think colourful, chunky sneakers, a hoodie and some street-friendly accessories, like a dad cap or cross-body bag.

For outerwear, Johnson has a tip of his own for maintaining the equilibrium. “With this fit, I always try to add shape and balance to the upper half by using plenty of pockets to help with the proportions.”

Taper Fit Jeans

J.Crew

Strong thighs are a cross that some of us simply have to bear. Great for the gym, not so much the changing room, where many a fit of jeans will cut off circulation to your ankle. Thankfully tapered denim can provide some welcome and flattering respite.

“This fit is a dream come true for anyone with a rectangular body shape,” says Gilfillan. “And for those with bigger-than-average thighs.”

The wider leg and roomier seat of this cut is accommodates a thicker-set body shape, without sacrificing the narrow leg opening of some of the slimmer styles. But this doesn’t come without its drawbacks. For certain body shapes, tapered jeans are best left alone.

“If you have an exaggerated triangular body shape – ie. much broader at the shoulders than hip – avoid this shape as it could make you look top heavy,” Gilfillan says.

What To Wear With Taper Fit Jeans

To achieve maximum form flattery from taper-fit jeans, a good start is to forgo anything with a baggy fit or loose cut.

“You need to wear a shorter top with this style of leg-wear – not the long line T-shirts often worn with skinny jeans,” says Gilfillan. “You can also go for a bit more volume so a regular fit shirt instead of slim fit or a boxy, chunky sweater. Top that off with a shorter bomber jacket or alternatively go for an oversized raglan sleeve coat.”

To nail the footwear, stay away from formal styles and stick to sneakers. Something sporty is a safe bet and we’d recommend a retro runner or, alternatively, something simple and low-profile.

Regular-Fit Jeans

Scotch & Soda

As in all areas of menswear, trends come and go with alarming frequency in the denim department. However, one style that has remained steadfast since the very dawn of denim is the tried-and-tested regular fit.

This simple cut is to your legs what a plain white tee is to your torso. That is, simple, versatile and never out of style.

The regular cut’s straight-up-and-down design mean there’s no body shape it can’t accommodate. “It will look especially good on a larger guy,” says Gilfillan. “Particularly someone who may be short and stocky.”

What To Wear With Regular-Fit Jeans

Regular-fit jeans looked great in the 1950s, and Gilfillan suggests you look to the same period for styling inspiration.

“Try going with a flannel check shirt and work boots, or for a chore jacket and some heavy soled boots,” says Gilfillan. “They also look great with a turn up, but if you have short legs make it narrower as opposed to wider, as a thick turn up will make your legs look shorter still. For full lumberjack vibes, team your flannel shirt with a gilet and opt for a classic Levi’s 501. Obviously.