If you ask any stylish man to list two or three essential wardrobe staples, chances are a pair of dark wash jeans will be among them.
Jeans, in general, are casual, comfy, versatile and stylish - assuming they fit well, of course! But well-fitted, dark wash jeans just might be the most versatile type of jeans a man can own.
They’re easy to dress down, and they can even be dressed up a bit. They’ll never replace your wool trousers or suits, but you can definitely wear them with a jacket (and even a tie).
To make sure you’re getting the most mileage out of your jeans, we’re going to show you 10 ways to wear them, starting with the most casual and working our way up to the dressier looks.
Again, it’s crucial that your jeans fit properly. While fit will always be subject to trends and personal preference, we believe there are some universally flattering guidelines.
If you’re not sure how jeans should fit, check out this guide:
Jeans for Shorter Men: The Ultimate Guide ← Click to read
Note: despite the title, the above article is helpful for any man (of any stature) who wants to make sure his jeans fit and flatter his build.
Okay, now that we’ve got fit covered, let’s get into the outfits.
Outfit #1: T-Shirt and Sneakers
Jeans, t-shirts and sneakers go together like Crosby, Stills and Nash. They’re just cool, and they’re not going out of style anytime soon.
Here’s the best part: with dark was jeans, you can wear pretty much any color t-shirt you like.
Want to keep things simple and understated? Go with white, black or grey. Want to stand out a bit? Try light blue or pink.
Same goes for your sneakers. If you’re a Converse high tops kind of guy, that works just fine. If you prefer a minimal leather sneaker, that works too!
Outfit #2: Henley and Boots
Here’s another simple, classic combo that pretty much any guy can pull off with confidence.
The Henley shirt is very similar to the t-shirt, but it has a placket below the neckline with a short column of buttons. Most Henleys have long sleeves, although short sleeve versions are available.
Like boots, Henley shirts are rooted in function. Their utilitarian origins give them a rugged vibe that gels perfectly with boots.
This combo can be worn as-is, but it’s perfect for layering. Throw on a lightweight vest, leather jacket or field jacket, and you’re ready to rock.
Outfit #3: With a Polo
Another great thing about dark wash jeans is the fact that they can be worn all year round. Sure, they’re great with boots and Henleys in the fall, but they also look right at home with a polo shirt through spring and summer.
The polo shirt is the t-shirt’s handsome older brother. You know, he’s slightly more mature and has a steady job, but he still knows how to have fun on the weekends.
For footwear, you have choices here. Since polos are traditionally worn more in warmer seasons, we recommend sneakers, loafers or driving mocs.
If you need some extra warmth or protection from the rain, throw on a lightweight jacket like a raincoat or Harrington.
Outfit #4: Work Shirt and Boots
Here’s another rugged combo that’s easy to pull off. Just like Henley shirts, work shirts are rooted in utility. We’re not saying you need to spend your weekends woodworking, but if wear this combo, people will probably assume you know your way around a workshop.
Flannel work shirts would be our top choice for cooler months. Go for a more casual boot like a classic work boot, leather desert boot or suede Chelsea.
Feel free to layer your work shirt over a t-shirt or Henley. You can also layer a jacket over your work shirt for extra warmth and style points.
Outfit #5a: Button Up (Untucked)
If the weekend warrior had a uniform, it would be jeans and a “button down” shirt. We actually call these button up shirts, although some of them have button down collars. Either way, they look great when worn untucked with jeans.
Just remember: when you wear a button up shirt untucked, you have to pay attention to the shirt’s length.
We see lots of guys wearing dress shirts untucked. The problem is, dress shirts weren’t meant to be worn this way. They’re too long, and the shape of the hem doesn’t work (it’s too curved).
Casual button ups like our Weekend Oxfords are shorter and have a straighter hem. They hit right around mid-fly, which is the perfect untucked length.
With jeans and an untucked button up shirt, you can wear sneakers, loafers, mocs or boots. You also have your choice of outerwear - anything from a leather jacket to a topcoat.
It’s one of the most versatile outfits a man can wear. All hail the casual button up!
Outfit #5b: Button Up (Tucked)
Of course, you can dress things up a bit by tucking your shirt into your jeans. Some shirts, like our Everyday Shirts, are long enough to wear tucked in. Others, like most dress shirts, need to be tucked in.
While you can wear dress shirts with jeans, we prefer a more casual button up, such as an Oxford. Look for casual details like button down collars, chest pockets and unstructured cuffs (as opposed to the rigid cuffs of a dress shirt).
It’s important that you keep your shirt tucked in throughout the day. A well-fitted shirt will definitely help!
Outfit #6: With a Sweatshirt or Sweater
For a comfy, laid back look and feel that’s perfect for cooler weather, try wearing your dark wash jeans with a cotton or wool crew neck sweater.
On one side of the spectrum, you have your classic loopback cotton crew neck, a comfy throwback with athletic roots and a casual vibe.
On the more formal side of the spectrum, you have fine merino wool crew neck sweaters. These work best over a light cotton tee or undershirt.
Outfit #7: Sweater Over Shirt
Layering is the secret weapon of stylish men. When it’s cool enough to wear layers, be sure to take advantage of this classic combo: jeans, button up, sweater.
Leave your shirt untucked for a more casual feel, or tuck it in for an office appropriate look. We recommend keeping your shirt collar tucked neatly under your sweater, but if you like the “flyaway” collar look, that’s cool too.
If you wear a solid, neutral color shirt like white, grey or light blue, you can wear also any color sweater. Of course, don’t be afraid to add some patterned shirts to the mix. Gingham, stripes, microcheck and plaid are all solid choices.
Outfit #8: With a Vest
Just like jeans and boots, the quilted vest has an inherently rugged feel. In our opinion, it’s one of the most versatile and underrated layering pieces for fall and winter.
When wearing jeans, you can add a vest as a middle or top layer over a Henley, button up, sweater, long sleeve polo, or pretty much any other type of shirt.
Vests look great on their own (over your base layer) or under a jacket, such as a leather jacket or field jacket.
They add a bit of warmth and a lot of visual interest to any outfit, and they’re a perfect addition to any dark wash jeans outfit.
Outfit #9: With a Blazer
If your jeans are dark, undistressed and fitted, it’s not too hard to dress them up. The easiest way to do this is to tuck your shirt in and throw on your favorite blazer or sportcoat.
A navy blazer is always a good choice, but don’t be afraid to experiment with patterns like houndstooth and plaid, or different colors like grey, burgundy and brown.
At the risk of sounding like a broken record, we want to emphasize the importance of fit, especially in the sleeves. Your jacket sleeves should be short enough that they reveal about ¼” of shirt cuff. If they go past your shirt sleeve, they’re probably too long.
Outfit #10: Shirt and Tie
This is about as formal as you can go with jeans. You’ve already got your button up shirt, tucked in, and your jacket. Now it’s time to throw on a tie.
This is basically a business casual outfit, but we’re dressing the whole thing down by swapping the trousers for jeans.
A more casual tie works well here. Leave your solid red power tie at home, and opt for stripes or prints instead. Feel free to include a couple of accessories like a white linen pocket square or your favorite watch. Just don’t overdo it - one or two tasteful accessories is plenty!
For your shoes, you’ll want to lean formal, not casual. Go with loafers, bluchers, double monks or dressy Chelsea boots.
Make sure your jeans are the right length. Go for slight break or no break, and if you don’t know what that means, read our pants break guide.
If your jeans are too long, it will detract from this decidedly dressy getup.
Wear Your Dark Wash Jeans Well
We hope this article gave you a few dark wash jeans outfit ideas. No matter how you like to wear them, we hope you have at least one pair of go-to pair in your closet.
If you don’t have a pair of jeans that fits perfectly, check out our jeans collection. With three different cuts and 45 sizes, you might just find your new favorite pair.