Sasha I am dating this guy; well, we've been on a few dates with the promise of more. I like him and I know he is really into me but... I really hate the way he dresses. Can you get a guy to change his wardrobe? Obviously it is not something I would bring up now but if we become an item, is this something I can change about him? S


Michelle Williams indied Jason Segal, Justin Theroux has to match Jennifer Aniston's outfits, and Kanye gave what’s-her-face a total wardrobe overhaul.  These are just a few examples, but the best one - the one that makes me laugh every time - is Jennifer Lopez's masterful transformation of Ben Affleck into a massive Miami douche-bag (which is what she clearly saw in Marc Anthony).  No matter what you think of her though, she deserves a slow clap her on that one.   I mean, she spray-tanned the man and gave him a bouffant.

S, the point is, it can be done and it gets done all the time; the trick though is to do it gradually and on the sly.  Now I have to say that I think it’s a tad too early for you to bring out your eager stylist now, but once the two of you get exclusive, you'll have the green light to re-wardrobe the sh-t out of him.

Let me’s his shoes.  They’re heinous, right?  This is where most men f-ck the dog – they’re either still wearing orthopedic university basketball shoes or gross dress shoes with bootcut jeans.  It’s a vagina killer, I know.   So my advice would be to start from the bottom and work your way up.

Here’s how to do it:  Gifts. 

And lucky for you, the timing couldn’t be better because Christmas is right around the corner.  So S, it’s time hit the mall and buy him some entry level items: like a pair of chucks, a good button-up and if you have some dough to spare, a pair of slim cut pants of your liking.  If you comb the sale racks you can get in and out for just under 150 bucks.   

Look, if he’s not a total dummy he’ll get the hint and play along.  And then one day S, one day you’ll finally get to the point where I am, where if you catch your man in an ugly outfit, you can shame him into taking it off himself. 

(Lainey: none of this has ever worked for me. Jacek wears track pants and last week I bought him a beautiful striped sweater with buttons on the shoulder and he said I was forcing him to look like a sailor. So there’s that. )

Hope this helps and keep you can reach me with your Life + Style questions here.