What to Wear: Valentine’s Day

I will never forget the one time I went out on Valentine’s Day with the guy I was dating and I put on a pretty Alexander Wang dress and he, well, he looked he made no effort, wearing the same jeans and chambray shirt he wore any other day of the week. Now if he had put on outfit like the one above, I would have felt like a million bucks. We went out to dinner at a nice Japanese restaurant and then for drinks to one of the nicest spots in New York, the Top of the Standard. Dita Von Teese was set to perform a burlesque set, and I wanted the night would be perfect. Instead he bought one drink for us to share (cheapskate!) and insisted he go home before she even went on stage. While I wasn’t completely upset, I did think that Valentine’s Day was a little lackluster and I did feel overdressed. Yes, I know Valentine’s Day is bullsh*t, a holiday invented so that greeting card and candy companies could make an extra dime off of our emotions, but still, he could have made a little more effort. I’m not saying you should make a grand gesture, but just try. Think about your plans. Now if you’re planning a quiet night in, or a casual dinner then by all means, feel free to wear your normal clothes. Are you going some place nice? If so, step up your wardrobe game a bit! It’s that easy. If you’re not sure, just ask her what she’s wearing, and plan accordingly. Trust me, it will make her all the more happier.

Clockwise, L-R: Suitsupply Napoli Blue Plain, $399 at us.suitsupply.com. English Laundry Trim Fit Dress Shirt, $98.50 at nordstrom.com; Neiman Marcus Solid Bias Ribbed Silk Tie, $24.50 at lastcall.com; Beckett Simon Goodyear Welted Fletcher Derby, $134.99 at beckettsimon.com; Geoffrey Beene Men’s Chevron Stripe Solid Brass Suspender, $27.50 at amazon.com