We’re back from a vacation that was very much necessary. We’ll start off the proceedings with a common query. This one’s from Jessica in Long Island: “My date showed up dressed way too casual. We were going to the theater and to a nice restaurant afterward. I still had a good time, but am not sure how to let the person know to dress more formal the next time.” First off, you can look at our two installments of “First Date Fashionista” (click here and here).

We know how hard it is to tell your date to do something after just one meeting. But there are subtle ways to let him know that he may have under-dressed your first time out. Did he know what restaurant you were going to after the theater? Now that you’ve established you want to see him again, wait for that phone call and make a suggestion or two for places to go. That puts the ball in your court. When you’ve got a place that might require some dressing up (may we suggest Atlantic Grill next time you’re in Manhattan? That might force the issue) and when he says “yes,” mention that they’re slightly more formal than other restaurants in the city. “You may want to wear a blazer” is less subtle, but it could work for certain guys.

That said, if he shows up and is what those in the know call a “hot mess” (or even just “hot casual mess”) then you know he’s not a dresser-upper. Once is a coincidence; twice is the possible start of a trend. Jessica, if you like the guy but don’t like how he dresses, that might be something you can fix down the road. But clothes really do make the man: if he doesn’t like to “strangle himself in a tie” when necessary or put on a non-ripped pair of jeans to go out to a club, then you know you’ll have a fight or ten down the road. It’s not the worst thing to fight about, but these are the kinds of things you need to think about in terms of the long-term relationship you may share with Dr. Dress-down. So keep it subtle on the phone or email, see what he shows up in. Decide next if you want to force the issue if he’s worth it and then, if he is, the next step is to be at his place and pick out something for him to wear. We really hope he’s worth it in that case! Good luck.

Here’s a guide to first-date wear for women and one for men. Men’s Health has a comprehensive guide too…we’d suggest using this one before picking out your attire, gents.

And post your thoughts below. How else should Jessica tell her man that he’s too casual?