Shirting, the Issue

I’ve been dating a guy for six months and at the beginning of our relationship he always looked great when we’d go out. Lately I’ve noticed his sense of style is going downhill fast. Instead of always looking crisp and put together, he’s now sporting dirty jeans and T-shirts whenever we go out. How should I handle this?

Have you tried pointing out that he looks really, really casual for a dinner date? If he says that he wanted to be “comfortable”, remind him that he can still be comfortable in a nice button down oxford shirt. Try reminding him before the next date that you’re going to a nice place and he needs to kick up the wardrobe a notch. If that still doesn’t work, have a conversation with him before your next outing and ask him about it. I’m sure he has a reason but I’m even surer you can make him understand the importance of looking sharp.

I’m stuck on what to give my boyfriend for our one-year anniversary. I’m not ready to give him a ring, but I want to give him something super nice.

Not knowing your budget or what his style is like, here are two safe suggestions. One is a piece of jewelry you know he would wear, such as cuff links or a bracelet. The other is a fantastic dinner followed by an overnight in a nice hotel. A nice accompanying gift would be a framed photo of the two of you with a handwritten love note. Happy Anniversary!

My mother-in-law gave me a horrible sweater for Christmas and although I gracefully accepted it and thanked her, I would never wear it. She’s coming to town and my girlfriend says I have to wear it while she’s here.

You should let your girlfriend’s mother see you wear it. However, if it’s as horrible as you say simply throw a denim jacket over it. Denim jackets can cover a multitude of sin, sweaters included. And for the remainder of her visit, let her see you in your style so she can get a better idea of what you like.