At some point, a “good fit” in men’s jeans seemed to mean getting as close to the legs as physically possible. Everything was slim, then skinny, then somehow even skinnier. I never understood why a little extra fabric became such a crime.

Skinny jeans had their moment. They looked great on some men. On others, not so much. That doesn’t mean they need to disappear, but I’m glad there’s more room in men’s fashion again. Literally.

Baggy jeans have a look I enjoy. The denim hangs instead of clinging. The shape is a little more relaxed, a little less concerned with showing off the body. And they give even a plain T-shirt and sneakers some character.

I also like that they don’t belong to one particular type of man. There’s the full skate-inspired version, with wide denim and battered sneakers. There’s the cleaner version with darker jeans and a simple sweater. They don’t have to look anything alike.

Not every outfit needs to be smart casual

I love classic menswear. A well-cut jacket and a good pair of leather shoes will always have their place. But I don’t want to dress as though I’m heading to a dinner reservation every time I leave the house.

In Canada, much of everyday life is pretty casual. Hoodies, denim, sneakers, practical jackets. That isn’t a failure of style. It’s how people live, especially when comfort and weather matter more than making an entrance.

And streetwear has its own sense of taste. A faded pair of jeans, an old sweatshirt and the right sneakers can look better than an expensive outfit that feels like it was put together for approval. The clothes don’t need to look new. I actually prefer a little wear in denim.

Of course, baggy jeans can look ridiculous. I’ve seen the sort of exaggerated silhouette where the shoes practically disappear and the hems sweep the pavement. I’m not going to call every oversized outfit genius just because it’s fashionable.

The Canadian winter doesn’t help, either. Jeans dragging through salty slush aren’t exactly an appealing image. But that’s a practical complaint, not a reason to write off an entire style.

I’m more interested in personality than rules

What bothers me about fashion advice is how quickly personal preference becomes a rule. Wear this cut. Avoid that cut. Men over a certain age shouldn’t wear this. It’s exhausting. Sometimes a guy just looks good in what he’s chosen, and that’s enough.

I wrote before about why fit matters more than brand names. I still believe that. But fit isn’t another word for tight. A loose pair of jeans can fit exactly as intended; a slim pair can look completely wrong. That’s the point.

I don’t expect baggy jeans to be everyone’s favourite. Some men look better in straight-leg denim, and some are never giving up their slim jeans. Fine. There’s no need to turn a trouser shape into a personality test.

I’m just glad men’s clothing feels a little less restricted again. I’ll take a good baggy outfit over another pair of sprayed-on jeans any day.