A Gentleman’s Guide

How To Make A Beanie Work For You

The streetwear favourite has been upgraded – we take our hat off to the fresh new ways to wear it

  • Photograph by Ms Carola de Armas/Blaublut-Edition.com

The lowly beanie – the exclusive preserve of “resting” actors, former X Gamers, and extreme snowboarders, right? Wrong. The beanie’s all grown up – you’ll now find cashmere and merino wool versions alongside the more traditional cable knits. And, with winter approaching, its modern iterations put a crowning spin on everything from tailoring to chunky sweaters and refined rollnecks, while still keeping things nice and toasty. Scroll down to discover seven seasonal ways of putting the haute into woolly hats.


  • Photograph by Frenchy Style/Blaublut-Edition.com

All the good guys in history, from The Lone Ranger downwards, have worn white hats; this gentleman keeps the noble tradition alive with a chunky cable-knit beanie. There’s no unwritten rule that says you have to match it with a sweater – though the white-out makes a strong, snowdrift-ready statement – but the way he contrasts textures with his worsted wool overcoat is certainly worth serious cool consideration, whether you’re hunting outlaws on the Texas plains or tracking down a warming almond latte. (And if you can’t get white quite right, a lighter neutral shade will still mark you out as one of the goodies.)

Get the look



  • Photograph by Mr YoungJun Koo/Lickerish

Does the thought of a beanie bring to mind the shapeless blob crammed on the bulbous head of Cartman from South Park? Well, this gentleman proves that the correct application of a classic ribbed beanie – pulled down low, tweaked up high – can top off a seasonal ensemble with shapely aplomb. We’re also liking the backwoods-forager-goes-to-Pitti stylings of the robust rollneck, the Navajo jacket, and the more-vertiginous-than-high-tops. Two words: Prime. Rib.

Get the look



  • Photograph by Mr YoungJun Koo/Lickerish

Eternal menswear style dilemmas: should jeans “stack” at the hem or get cuffed? Can stockier types pull off the “health goth” look? Can you wear a beanie with tailoring? The answers: either, according to taste; why on earth would they want to; and but of course, if you follow the lead of this gentleman (the impeccably dressed fashion director of American Esquire, Mr Nick Sullivan), and team the darker tones of a soft beanie with your scarf to offset the lighter, crisper shades of your overcoat and jacket. We’d say “sprezzatura” if this look wasn’t so completely, and genuinely, effortless.

Get the look

  • Enlist Virgin Wool and Modal-Blend Coat



  • Photograph by Mr YoungJun Koo/Lickerish

Two rules of thumb when opting for a patterned beanie: avoid acidic colour-clashes, unless you’re single-handedly attempting a revival of 1990s rave style; and ensure that the motif breezily riffs off the rest of your outfit. This gentleman triumphs on both counts, thanks to a jaunty-but-not-gaudy design that recalls the graphics of the Space Invader machines on which many of us whiled away our misspent youth, and the way it contrasts-complements the herringbone of the overcoat. As those old consoles used to say: game on.

Get the look



  • Photograph by Frenchy Style/Blaublut-Edition.com

The joys of winter: a roaring log fire. Toasted marshmallows. Cranberry cocktails. And layering. The chance to combine three or four tiers up top – overcoats, jackets, jumpers, scarves – and play off their colours, textures, cuts and shapes, with the beanie – pulled low, tugged higher, picking up on a tonal shade, or going its own sweet colour-pop way – providing the crowning glory. These gentlemen add a few refinements – winter-sun Wayfarers, pocket squares, standby gloves – in order to, if you will, strata their stuff.

Get the look



  • Photograph by Ms Suzanne Middlemass

Was this gentleman thinking of the quote by the Cubist painter Mr Fernand Léger – “Man needs colour to live – it’s just as necessary an element as fire and water” – when he put this outfit together? Probably not, but it’s a great example of the dictum, with the radiant red of the beanie taking the subdued-but-refined navy-and-black ensemble to another level. The box-fresh haute sneakers (just out of shot), also keep things classily smart-casual, if not modern-artful, at ground level.

Get the look



  • Photograph by Mr Adam Katz Sinding/Trunk Archive

The novelty beanie: discuss. Admittedly, there was a time when such a concept languished, in style terms, somewhere beneath fake tuxedo T-shirts or piano-key ties; but now, with everyone from Gucci to Valentino adorning their beanies with the likes of Mickey Mouse and snarling dragons, it seems to have come in from, and indeed with, the cold. This gentleman homages Hanna-Barbera with a Tom and Jerry motif; we wouldn’t mind a retro-style Hong Kong Phooey number, but we might draw the line at SpongeBob SquarePants.

Get the look

Cooler heads prevail

The people featured in this story are not associated with and do not endorse MR PORTER or the products shown