A controversial opinion: jeans might be holding us back from achieving winter wardrobe nirvana.

What is winter wardrobe nirvana? That thing where you never have to think about what you’re going to wear because you like everything that’s in your closet and have the perfect amount of shit — not too much that you’re overwhelmed and annoyed at yourself, or too little that you’re underwhelmed and naked.

Why are jeans potentially holding us back? Because for winter, shoes are essential to nirvana, and most winter shoes/boots — the practical ones we need to get from point A to point B in freezing temps — look bland as a steamed potato with jeans.

So maybe the first thing that makes a pair of winter boots good is actually acceptance of the inconvenient truth that from a probably-purely-aesthetic perspective, you might need to venture beyond the territory of jeans. Like into another durable but still presentable fabric like corduroy or gabardine or velvet (or tbh, technical jersey works too!) — preferably bonded by rigid-enough cotton that holds form and like, wants to hug your legs.

My choice for length is about an inch above the ground and the shape is a slight flare — they’re easier to get the boots over. I like a high rise, but mid-rise is good too, just make sure they’re not pleated because more likely than not you’ll match them with a big sweater when you’re not entertaining lurex polos, and pant pleats don’t look particularly good with anything that’s not tucked in. Like you want to accentuate the fupa, not hide it. You know? So there’s an express lane explanation of that. Now on the boots.

Measure them by:

Can they withstand frozen grounds, chunks of ice? Will it break your tender heart if salty floors decorate the toe of your shoes with that marbleized white imprint that kind of looks like a dried toothpaste stain?

To the point above, how much do you wanna spend on your practical boots, like if the odds that they get stained with salty toothpaste residue aren’t particularly low but you also wanna know you don’t have to think twice about the pair’s longevity (eg they will serve you for seasons to come)?

What color are they? How tall are they? Must you tuck your pants in (like, are they moon boots) or can you leave them out? How many ways can you wear them and for how many kinds of occasions?

Ideally, you wanna be able to put them on with like, a sequined jacket and feel like a million bucks but not like you stole the money, like you earned it which means no imposter syndrome here, pal!

And in the same breath, you want to be able to wear them to visit your friends upstate, who have described the town dress code as “we raise our own chicken then serenade them and wouldn’t dare to eat them, unless we get hungry,” so figure like a fleece-lined anorak and sweatpants.

It might change the big upstate energy — but feel free to exercise your creative license on that dressing formula (two-ply leggings instead of sweatpants, quilted jacket instead of anorak; am one balaclava short of an apres-ski trip) and maybe commit to one or the other as far as the chicken goes.

The closest I’ve come to the best shit-weather boots features, as evidenced above, laces that start at like, the toe of the shoe and travel up to the other end, where your ankles are. The toe is either very round (like on a traditional hiking boot) or almond-shaped, like on the pictured pair of Grenson boots. It is helpful when the laces traveling up the shoes are a different color from the actual shoe because it will give your boots its orange zest of life. It’s like the difference between drinking Pellegrino (wearing pants) solo (with single-tone shoes) or splashing in sum citrus (laces).

I’m not nuts about the fact that the toe points up slightly but it is a concession I’m okay making when the other alternatives are these on the literal end, and these on the fancy end. Or these if the Gucci’s not Goochy enough.

Wait, actually, the Columbia ones aren’t bad at all, just maybe more like sneaker incarnates as opposed to boot. On the same vibe page, I like these from North Face for $138 too and these for $140.

For $452, here is a pair somewhat similar to the Gucci’s. They’d look great if you swapped out the laces for red or yellow ones. I don’t mind these in green suede either.

What I like in particular about the Grensons, and this goes for the ones that don’t look as much like rainboots or sneakers too, is that they’re sophisticated enough but still practical, which is the venn diagram overlap I’m most interested in pursuing these days. Maybe I’m getting older, maybe it’s a mom thing, or maybe I have been back uptown for just long enough to be turning into my mother. Remains to be seen!

And not for nothing, I did try on the boots with jeans before sending this, so as to challenge my opening assertion.

I do believe I am on the precipice of standing corrected but I’ll let you be the judge of that.

Signing off love and other drugs,

Jake Gyllenhaal