How to Ruin a Classic Navy Suit, Demonstrated by Justin Timberlake

Don't be sad, Justin, we can fix this.

Justin Timberlake is, on the whole, not a badly dressed guy. Ok, he does occasionally fall into the sneakers + waistcoat + fedora = showbiz, babay! celebrity style trap, but he came of age during the Nineties, and these habits can be hard to shake. We get it.

What we don't get, however, is why he would potentially derail an (almost) perfectly cut suit with the most common misstep in the men's tailoring game.

We are, of course, talking about the curse of the ill-fitting trouser. An affliction that does not consider your wealth, status, or previous style history. It cares only that you drop your guard, lose your vigilance. It is all around us, waiting to strike, which is why must be aware at all times.

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Starting from the top-down, Timberlake's tailoring is pretty close-to faultless: His blazer fits perfectly, with just the right amount of pinch in the waist and cuff on show. And while there's perhaps a bit too much blue with the shirt and suit, he's done a solid job of offsetting the differing shades with a subtly patterned wide tie (just needs to be a tiny bit tighter) that complements the wider lapel of his blazer.

Unfortunately, all this good work is nearly undone with a pair of unflattering trousers.

(A moment of silence for all the great suits ruined by the baggy, please.)

While hardly the worst case we've ever treated, Timberlake's bottom half still serves to create the nightmare silhouette that makes him seem far stumpier than his actual height of (a very respectable) 6'0".


Even if his goal was more of a wide-leg old school look where his trousers stack slightly on top of his shoes, the fabric throughout the leg appears creased and billowy, which, with the help of a good tailor, could be easily transformed into a neat, straight (not skinny) trouser that ends with a considered stack on top of his Oxfords.

As with most things menswear, the difference between slick and sloppy usually comes down to not having the number of a reliable tailor in your phone. Even if the suit appears to fit perfectly off the peg, you still need an expert's eye to trim and tuck its imperfections.

It's still a nice suit, Justin. Anyway, at least everything is uphill (or maybe downhill?) from this iconic moment.


This story originally appeared on Minor edits have been made by the editors.

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Finlay Renwick
Finlay Renwick is the Digital Editorial Assistant at
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