Ask Bossy: My boyfriend dresses so badly. How do I tell him without hurting his feelings?

Hi darlings,

This week’s Ask Bossy dilemma comes from “Lucy”. She has a dilemma as old as time: a sartorially-stunted boyfriend.

Dear Bossy,

I have the most amazing boyfriend. He’s so clever, so kind, hard working and treats me so well. We have a great life together and have spoken about marriage – I can’t wait to be his wife! There’s just one thing….

I can’t stand his dress sense (or lack of it). He’s a good looking, tall, athletic thirty-something who dresses like a teenager. Think ten year old, big baggy jeans, t-shirts with printed slogans and oversized hoodies, and the wet gel look in his hair, on special occasions…

I’m not exactly a fashion editor but I do like to look smart and put together. People have asked me why he dresses like that and of course I just shrug it off, but it does show that it’s kind of obvious.

How can I give my man a ‘grown up eye for the straight guy’ makeover without coming across too superficial or hurting his feelings?

Aw shit. Lucy needs some REAL TALK. And Bossy gives it to her STRAIGHT: (Post continues after audio.)


But, like Mia says, a badly-dressed boy can interfere with your sexual attraction. So what are the wily ways women wrangle wardrobes?

There’s many ways Lucy. Here’s how:

Among the tricks:

  • Give him a wardrobe cleanout
  • Start gifting him clothes for every birthday/christmas/party/event in your life.
  • Take a bunch of clothes to the laundromat and have the “machine” “accidentally” “eat” them
  • Trip in the laundry and sploosh bleach on those holey t-shirts
  • Start secreting away clothes, one at a time, funneling them out of the house very slowly so he doesn’t notice, and when he says “Have you seen that t-shirt/hoody/tub of gel?” smile sweetly and say “yeah! You had it when we were camping! It must still be in the back of the car…”
  • Or, like Bossy says, grow up. And focus on why you love him, not the hoodies he wears. #boom



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Also in this week's episode of Mamamia Out Loud, what’s wrong with calling women “hysterical”? It's called 'gaslighting' and it's worth knowing about. And do you believe in love? Do you believe in Hiddleswift? You won’t after you hear about PRomance. Plus, the drastic decluttering strategy that promises to end clutter coming into your house. It's the podcast that won Best New Show in itunes:

For more episodes of Mamamia Out Loud, subscribe in iTunes, or download the show on your podcast app of choice (like the Mamamia Podcast App!)