I have a thing about a guy in a cute outfit (good jeans, cool shirt, and a "fashion-y" blazer or leather jacket) paired with a really, really great pair of...sneakers! Now, I do not mean Nikes. I do not mean the sneakers you wore to the gym (gag...). I do not mean I-think-I'm-Kanye-in-pretentious-Gucci's. I want to see you in a pair of sneakers that says you are a grown-up but still have a little bit of a cute kid in you. I want to see you in a pair of sneakers that says you understand the difference between the types of sneakers that exist. I want to see you in a pair of sneakers that shows your desire to express yourself with the occasional unexpected choice, but that you also know when it's appropriate to wear them and when it isn't! (For the record, a second date is a good time...a first date is not. Dinner at the hot new downtown restaurant is...dinner with our parents is not!)
A perfect example of the "right" way to do dressed-up sneakers (by the way, even though us women are uncomfortable in our shoes about 90% of the time, we do not want you to be...which is part of the reason we readily endorse the cute sneaker!) is this pair from Converse by John Varvatos. This long-time collaboration has brought a ton of collections to the discerning male shopper, and this pair is actually pret-ty amazing. In washed black leather (I am not condoning the canvas versions for anything that involves "going out"...) with a contrasting white logo, these work perfectly as shoe-alternatives. They still have that great, iconic Converse low-profile, but also have a little weight to them. Make sure you wear jeans that aren't hemmed for your favorite go-to boots (they will be too long and bunchy, making you look shorter), and keep everything else in your outfit fitted and well-tailored (slim jeans, a great-fitting jacket) so you don't ever look sloppy.
Super comfy, a little fashion-forward, and editor-in-chief approved. You're welcome, boys.