Sienna Miller was a glossy vision of put-togetherness at the 2013 Outer Critics Circle Awards last night in New York, where her fiancé Tom Sturridge picked up an award for his role in the Broadway play Orphans.

While Sienna was radiantly golden, all perfectly coiffed with neat minimal make-up, Sturridge was altogether scruffier, as is his wont. Because despite talk of Burberry contracts and an offbeat but successful Hollywood career (this untitled Terrence Malick project looks particularly interesting), Sturridge is a man who looks like he trips over untied shoelaces and wears jumpers with holes he can stick his thumbs through.

Which is endearing – almost. There is something winning about the scruffy man, a guy with greater concerns than cufflinks – nobody, really, besides Kim Kardashian, wants to go out with a fashion obsessive like Kanye – but dating a chap liable to wear an updon’t or turn up to the Met Ball with his suit tucked into his boots must be a chore. 

Sturridge is a man likely to let you down, sartorially speaking, on any given day, equally inclined to turn up wearing a preposterous ensemble to either a casual lunch or a red-carpet event.

Most men, on the other hand, are actually safe bets at occasional dressing. They put on a suit, one you helped them pick out, and that’s the end of that. It’s during the day that they encounter problems. Marcus Mumford scrubs up well but when he and his wife Carey Mulligan abandon the premieres and parties, the discrepancy in style become obvious. While Carey looks low-key chic and still smartly cool, Mumford just looks like somebody who has grabbed whatever was on the floor. A hoody with a tailored jacket. No! You Just Never Do That, OK?

Prodding naturally scruffy boyfriends towards good everyday dressing takes a little more work than suit buying. They tend to balk at the price of really soft but ultimately quite nondescript T-shirts by designers and brands they have never heard of. Sample sales are a good place to start as you can cajole him into buying on the basis of bargains. Small, standalone stores are another good bet; they like the indie vibe and the big department stores are likely to overwhelm sweetly shabby boys.

Reinforce through compliments – ‘Wow you look so great in that YMC shirt and those Maison Martin Margiela jeans, sweetie’– and remember never to be over-the-top critical. Think, before you admonish, ‘Would I criticise my best girl friend so baldly?’ and if the answer is no, rephrase and find a nicer way to be mean.