A good pair of jeans to wear with a sports jacket should have the following “dressy” features:

  • Close fit. They don’t have to be skinny jeans, especially down below the knees, but there shouldn’t be any sag up around the thighs and crotch. You want a smooth outline of your body, not a drape of loose cloth that you can wave back and forth.
  • Dark color. Deep indigo is most common, but grays and black are also typical choices for nice jeans. More fashion-forward men may also experiment with white or very light gray jeans, or even brighter colors, but beginners should stick to jeans that are darker than the jacket.
  • Proper length. You’re going to be wearing nice-looking shoes with most of these outfits, and the cuff of the jeans should rest very lightly on the tops of the shoes when you stand straight.

Other style details that aren’t mandatory but help you look  more dressed-up include contrast stitching (where the seams are done in a color that stands out, such as orange or yellow on dark blue jeans), “natural” dyes with an uneven fade, and in some cases designer labels or trademarked stitch patterns.

You want to stay away from fashion details that make the jeans look more worn, even if it’s a deliberate fashion statement:

  • Severe fading or “acid wash” patches
  • Rips or tears of any kind
  • Fraying at the cuffs and pockets
  • Cargo pockets or gear loops

That’s not to say that some men don’t wear deliberately distressed jeans with jackets, but it’s a fashion-plate look — affected and a little over-the-top. Don’t experiment with it if you’re just trying to look a little sharper.

What Jacket Styles to Pair with Men’s Jeans?

The other half of the equation is your jacket.

There’s a huge range out there to choose from, and no one “right” style. But think about a couple important factors when you choose one:

Casual Jacket Fabric – This is more important than a lot of guys realize. A very fine, worsted wool jacket pretty much screams “suit jacket” to a practiced eye. It can work with jeans, but it’s not the unthinking casual ease of something more relaxed like corduroy or a visible twill weave.
Relaxed Jacket Cut – The advantage of any men’s jacket is the added definition, but don’t overdo it. You don’t want a razor-edged Italian suit here. A little softness in the shoulder is good, and the taper at the waist shouldn’t be too extreme. For tightness, remember the name of the garment — it should be loose enough that you could do “sport,” i.e. hunting and hiking in the countryside, comfortably.
Bold Jacket Color & Pattern – A solid jacket is fine, but you’re not going to be wearing it to any business meetings. Have a little fun. Colors like browns and grays work well, as do patterns like windowpane checks and plaids. In general, keep the dominant color lighter than your jeans, and if you’re wearing blue jeans steer away from navy blue jackets.

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