I’ve never met anyone – guy or girl – who enjoys shopping for jeans, have you?

It’s a notoriously discouraging process. Before you can even make it into the fitting room, you have to sift through ten styles in twenty different washes and where are you supposed to start anyway? After a go-round in front of the fitting room fun mirrors, with those obnoxiously unforgiving bright lights (why do they light stores that way anyway? No one looks good under those things), you inevitably leave the store feeling too fat, or too skinny, or too short, or too tall to buy anything.

That’s why I felt reader Ben’s pain when he wrote to tell me:

I am working on upgrading my wardrobe. In your archive I came across a post from last year on jeans, suggesting “a pair of dark, straight leg denim. Un-whiskered. Non-faded. Just a simple, dark wash pair of good-fitting jeans.” For the first pair of jeans, are we talking black, deep navy, or something else? Where to start?

 

It got me thinking, it’s probably time for a refresher on the type of jeans that girls want to see guys wearing, so here goes. I want to make it easier on you – at least a little. I can’t do anything about the size of your waistband, or the length of your inseam, but I can tell you the kind of jeans a woman wants to see you in, and a few tips on how to find the right pair for you.

STYLE

Guys look best in a dark rinse, straight leg jean. Across the board. Universally speaking. End of sentence. Period.

The silhouette is slimming. The color is appropriate to dress both up with a blazer and dress shirt, or down with a t-shirt and sneakers.

At the store, let the tag’s descriptions guide you. Look for labels that read “slim” or “straight.” Avoid “classic” or “relaxed” fits at all costs. These will be roomy and, while comfortable, totally unflattering.

Straight leg jeans should be the same width from your knee down to your ankle. Before you take a pair of jeans to the fitting room for a spin, fold the bottom hem up to the knee – they should be the same size across.

AG Jeans ‘Geffen Easy Slim’ Straight Leg Jeans in Roast, $188

FIT

Your denim should hug your legs pretty closely, while still allowing for a normal range of movement. You probably won’t be able to join in a game of pick-up basketball, but you should be able to sit, stand, and walk comfortably – even run briefly if you do that thing where you trip on the sidewalk, but to save face you break into a short jog to convince people you totally meant to do that.

The jeans should be fitted in your upper leg, which may feel strange at first, but don’t worry – you’ll get used to it.

At the store, sit down in the fitting room to make sure the jeans you’ve chosen aren’t too tight across the hips and waist. See if you can do that awkward thing your seventh grade math teacher did when he put his foot up on your desk while lecturing to seem “cool” and “with it.” If you can pull it off without splitting your pants, you’re good.

Naked & Famous “Weird Guy” in Dark Blue, $158

COLOR

Look for a deep, saturated blue that’s almost navy. If you’re not sure, the words “raw” “inky,” “selvedge,” and “dry” are good indicators of a dark wash. Avoid shiny fabrics, superfluous patches, and any whiskering or fading.

RISE & WAIST

Go for a medium rise – approximately 10-12 inches, though you may need to go into higher numbers if you’re on the taller side. With jeans that truly fit you, you shouldn’t need a belt (though I think they help a guy’s outfit look “finished”).

WEIGHT

Look for heavy-weight and mid-weight fabrics. Jeans that feel too light probably won’t last very long.

Don’t be afraid of denim that feels rough or stiff; they’ll soften up with wear.

CLOSURE

Okay, real talk. I like a button fly for its dogged determination not to do that thing that a zipper does where it starts to slowly split apart, like a married couple whose communication has broken down after years of comfortable silences.

But I get that if you are trying to get your pants off in a hurry (gahhhh), then a button fly can be, umm, cumbersome. A heavier weight denim should help keep jeans in their place, but if you are afraid of accidental exposure, go button.

LENGTH

Your jeans should sit on your shoe or just below it – no bulgy, sharpie-like wrinkles from an excessive break for your grown man denim. If the jeans you’ve found are perfect but too long, don’t be afraid to take them to the tailor. Sometimes guys think tailoring should be reserved for “bigger” or “more important” projects like suiting, but a pair of denim that fits you just so and hits at just the right point is definitely worth the extra money spent.

For even more on the in’s and out’s of a grown man’s denim wardrobe, check out Esquire’s “How To Buy Jeans”

And for more of my straight leg denim picks, head over to Polyvore