One foolproof, easy-to-nail, rom-com tried-and-tested look.
If you take one thing away from 2005 Christmas rom-com The Family Stone (besides a deep appreciation for the film’s brave confrontation of the complexities of the American family) let it be this: You should wear a hoodie and an overcoat to your next date. Let me explain. There’s a scene towards the end of The Family Stone when Dermot Mulroney runs dramatically through the snow on Christmas Day. He has a sexy little gash on one cheek (from a fight!) and he’s wearing a gray hoodie under a black overcoat. He looks hoodie-tough but overcoat-classy. He looks like he hit the gym earlier and then went to a fancy lunch at the hot guy club. He looks like he can afford two layers. He looks good.
Mulroney has so many lessons to teach us, such as how to diplomatically correct people when they confuse you with Dylan McDermott. But the most important lesson is this: In life, but especially on dates, people judge your outerwear. You may say, from deep within the down cavern of your Eddie Bauer parka: “I’d rather be warm than look good, and I’m only wearing my jacket between locations!” But unless you live in a truly arctic wasteland like Milwaukee, that’s the wrong attitude. On a date there’s no first impression grace period while you peel off your assorted fleeces; first impressions are formed as soon as you walk into the bar. Women know this, which is why we constantly sacrifice warmth in pursuit of a certain aesthetic. (The faux fur jackets that all the cool girls are wearing right now are not warm—they let the icy air in through every synthetic pore. It’s called suffering for fashion.) Fortunately for you, the sexiest outerwear a guy can wear to a date is also very cozy.
Which brings us back to Dermot Mulroney. His hoodie-overcoat combo is appealing for its perfect balance of casual and formal. Neither component can exist without the other: You’ll look slovenly if you show up to a first date in just a hoodie, and you’ll look like a rich murderer if you show up in an overcoat over a suit. But put them together and you’re the upscale hamburger of men, impressive but accessible. Texturally, the balance is sublime. Women are very tactile, and the scratchiness of the woolen overcoat is the yin to the hoodie’s soft yang. Throw on a beanie so she wants to touch your head too. Layering also makes you look swole-er.
The best thing about the Dermot is how difficult it is to fuck up. Almost any hoodie looks good under almost any overcoat. You can opt for Mulroney’s safe gray and black combo, or if you’re working with a camel coat you can layer with red to look like as confident (and festive) as this guy. If your overcoat is really bold, like this one, then you probably don’t need my advice. One caution: Do not attempt to layer a hoodie under an overcoat that is too small to accommodate the extra girth. If you can’t put your arms down when you’re wearing both layers, either the hoodie is too plush or the coat is too tight. In either case you must abort, lest you arrive at your date looking like you’ve had a post-teen growth spurt. Beyond that, don’t overthink this. When the cardinal style sin of a first date is looking like you tried too hard, this look’s thrown-togetherness is what sells it.