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Playing dress-up vs. helping someone dress

My boyfriend and I have been dating for almost a year now. Everything is going great, with one exception: he still dresses like he’s in high school. Saggy jeans, baggy hoodies, chunky sneakers, and skater logos everywhere else. How can I get him to dress a little sharper without coming off as a nag? Signed, Make Over Politely Expected

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By Thomas Palakon (Contributor) – Email

Image credit: Wikipedia Commons

Image credit: Wikipedia Commons

fashion and manners for the modern UFV gent, runs every week in The Cascade’s Culture section. Questions, comments or suggestions may be submitted to Mr. Palakon through seamus@ufvcascade.ca.

Another letter from our growingaudience!Dear Mr. Palakon,

My boyfriend and I have been dating for almost a year now. Everything is going great, with one exception: he still dresses like he’s in high school. Saggy jeans, baggy hoodies, chunky sneakers, and skater logos everywhere else. How can I get him to dress a little sharper without coming off as a nag? Signed, Make Over Politely Expected

You’re in a tough spot, MOPE, but you deserve to be applauded for recognizing the real pitfall in your request: how to tell someone they dress hideously and yet get them to buy into change without coming off as a shrewish control freak. It’s a fine line, but I assure you — it can be walked.

The most effective technique here is to start by putting your money where your sartorially concerned mouth is. I wouldn‘t recommend splashing out on a full wardrobe, but a few key pieces can lay a good groundwork. Start simple: a fitted black t-shirt or a casual, button-down Oxford, perhaps paired with straight-leg dark blue jeans. It’s certainly nothing too controversial, and when you comment on how great it looks, he’ll likely be more receptive to such gifts in the future.

It might be worth the effort in making a short list of his heroes, particularly in film or sports. Actors almost universally have a decent sense of style (they hire people like me to help them) and athletes are bound by team dress codes, and therefore are often (if unwittingly) well-suited and booted. By pointing out the dress choices of men he admires, be they anyone from Benedict Cumberbatch to Sid Crosby, you could be helping him see clothing as something truly aspirational, rather than merely functional.

There is also the possibility that your fella doesn’t dress up because he doesn’t need to. Are your social lives all about spending a bit too much time with Shomi and take-out? Get out and about: go to parties, or offer to spring for a proper slap-up dinner or a night somewhere borderline swank and cocktail-oriented when you have the chance to celebrate something in your lives. Effort begets effort, and any gent with a conscience will at the very least make a little extra appearance effort for his partner when he sees how excited she is to show him off to the town. There’s hardly any good reason to tuck in your shirt when your big date night is re-bingeing Mr. Robot and falling asleep on the couch.

But ultimately, the best way to make headway with Agent Volcom here might be to simply talk to him, like a grown up. You’re obviously motivated by more than a little self-interest here, but there is room for altruism in helping someone put effort into their dress sense. The important thing is to be helpful without being judgemental, or worse, manipulative. You yourself said you and your gentleman friend have a strong relationship. In the bigger scheme, love (or even something close to it) beats out having to date someone who doesn’t need to own an iron. And it’s not even close.

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