The Art of Young Manliness: The Sweaters your Grandma never gave you

We’ve made it to the dead of winter, and people around the country are gearing up for their second awkward family reunion of the season. That second time where all of our adorably oblivious grandparents, crazy uncles, slightly nosy aunts, and distant cousins we never talk to get together to open presents and share all the things that happened to them in the month between Thanksgiving and Christmas.

As a family tradition, you may end up going out to a holiday movie or taking a trip to the ice rink in San Francisco. Regardless, a successful guy is always on top of his stylistic game, and always prepared for the off chance an encounter with a girl on the rink or in the theatre could lead to something more. Unfortunately, I have news for you guys: that tacky sweater your grandma crocheted or even the one you picked out with your Christmas money may not be the best choice for making a good first impression.

Here’s the thing: outerwear is important. It’s the piece of clothing that shows the most, and in turn shows the most about the person wearing it. It has to be warm and durable, yet also stylish and practical for the situation. For example, a nine pound full-sized car coat would not be realistic inside an air-conditioned building, where you’ll do nothing but carry the bulky thing around or risk sweating your butt off. At the same time, that thin hoodie you love so much wouldn’t be comfortable after enough time outside your cabin in Tahoe, where the temperature drops well below freezing in the winter.

So how to choose? And what can one wear to leave a good first impression on a potential date?

Much like anything you wear, the coats and jackets you choose to don should reflect the kind of person you are. Are you the athletic, sophisticated guy who rocks The North Face fleece like nobody else? Or maybe you like the utilitarian and heavy look of a field jacket or peacoat. Regardless of your choice, it’s important to know how to create an outfit around that piece, and style your clothing appropriately.

For starters, it’s winter. We already can rule shorts of any kind out of the equation, which leaves jeans, chinos, trousers and joggers left to vy for the privilege of being your pant of choice. All of these bottoms have purposes, and all of them compliment certain types of sweaters.

The standard pullover sweater: simple, warm, classy and timeless, this clothing staple could turn the most inept dresser into a stylish and classy gentleman. They come in many forms, from the cable-stitched sweater (much more conservative) to the standard hoodie. But we want this piece to be dressed up, to scream a little more awareness and style. How do we do it? Easy.

Cable-knit and other conservative sweaters dress up decently with a dark denim wash jean and a brown brogue shoe or similar. It upgrades the look, while at the same time making that cable-knit sweater look much more flattering on a younger body.

Meanwhile the hoodie could be dressed up with some black chinos and a brown shoe, covered by a larger coat or a fashionable scarf. The options are endless.

Word of advice: stay away from full-length car coats and trench coats in high school. You’ll freak people out.

But there are many other options. Fleeces go well over polos and t-shirts, while big leather jackets and sport jackets go well with dress shirts. Tone down a sport jacket with a tee shirt and some dark denim, and then up the style on a leather jacket with a collared button-down and some black or brown chinos.

The key to style is balance, and knowing what pieces balance what. A rule of thumb is to do some simple math. Let’s say you want to be business casual. On my scale of 1-5, 1 being just a bit over sloppy and 5 being black-tie, the goal would be to hit a three. Each piece can bring you up one formality point or down. Leather jacket? Depends on the cut, but usually a +1. Denim? -1. Brown leather dress shoes? +1.

Add and subtract pieces until you hit 3 with a whole outfit. Once that is done, you can see what coat or jacket to wear.

So forgo the grandma sweater next time, use some simple math, and you’ll be catching girls’ eyes from across the rink in no time.