Other than physical signs like wrinkles and ptosis, perhaps the truest marker that one is getting older is a disdainful disconnect from the youth culture of the day. Whether it manifests itself in thinking that everything on the radio sounds like “noise,” or an inability to wrap your mind around “the Twitter,” these are telltale signs that you should probably just cash in your 401k and die already. Just teasing. But seriously, when you’re no longer cool, what is there left to live for?

Being a facetious jerk aside, one of those fashion trends that gets conservative types scratching their heads is oversized fits. Given that an impeccable cut is often the selling point to virtually any piece of quality clothing, it seems near sartorial heresy to purposely make things ill-fitting. However, this is fashion and things don’t have to make sense. Even menswear, traditionally known for its consistency and moderation, has caught on to the oversized trend. And no, we’re not talking about those boys who wear their jeans around their knees. That’s just disgusting.

So how does one rock the oversized trend? A good place to start is the sports luxe aesthetic. This mainly involves wearing work-out-style leggings (or meggings for guys) and an oversized, structural sweater or coat on top. Generally, aim for materials like scuba, neoprene, or thicker cottons so that you can get more shape and less bagginess. If you need an example, have a look at our favourite looks from the Alexander Wang X H&M collection. More designer inspiration can also be found on the runways of Stella McCartney, Rick Owens, Rad Hourani, and Public School.

If looking like a Parisian street fighter isn’t your steeze, you still have options. Ladies: aim for oversized tops paired with either skinny jeans, tights, or this season’s hottest bottoms, wide-leg trousers. On-point items for fall 2014 include oversized coats, scarves, fun furs, vests, shirt-dresses… if you can dream it big, you should wear it big. As a rule of thumb, hemlines should be low but sleeves and shoulders should be fitted to your actual arm’s length.

Gentlemen, an oversized parka, sweater, or long-line shirt will work. Long-line focuses more on the length of t-shirts, button-ups, and sweaters (going well past the waist) as opposed to just a general oversized fit. It’s all gravy, though. You can rock oversized and long-line items with a killer bomber, leather biker jacket, or underneath another shirt or sweater for a layered look.

Are you ready to go big or go home? If so, here are some super stylish ways to rock the oversized trend for fall 2014.