How to Wear Jeans With Everything: 6 Outfits to Pair With Jeans

We’ve got one rule when it comes to style—every man should have at least one good pair of jeans in his wardrobe. Jeans are that one piece of clothing that can be easily worn in almost any situation—dressed up at a cocktail party with a sport coat or dressed down at the park with a white t-shirt. Take a cue from our list of outfits that will make your jeans look good in any situation.

Here are 6 easy outfits to put together with jeans.

Stitch Fix men's outfit laydown featuring blue denim, grey t-shirt, plaid flannel button-up, navy puffer jacket and brown chukkas.

Option 1: The Fail-Safe

You can’t lose when you wear dark jeans with a lightweight puffer jacket, collared shirt and neutral chukkas. You’ll stay warm outside and can shed a layer and still look good when you move indoors. This should be the go-to combo for any guy that likes to keep it casual and the dressing simple.

Stitch Fix men’s outfit laydown featuring aztec shirt jacket over brown hoodie, next to olive jeans and brown chukkas.

Option 2: Rugged and Refined

Wearing a pair of jeans with a henley and Aztec patterned overshirt will give you a rugged and refined look. Top it off with some water-resistant footwear and you’ll be ready to take on any outdoor adventure from a bonfire on the beach to a cabin in the mountains.

Stitch Fix men's outfit laydown featuring khaki jeans, grey sneakers and cream and navy blue striped hoodie.

Option 3: Style and Comfort

Don’t overthink this—jeans are the ultimate comfort option. For those weekend days when you want to optimize for comfort without sacrificing style, throw on a pair of worn-in jeans, a hooded sweatshirt and suede sneaker for a laid-back but still cool look.

Stitch Fix men’s outfit with grey pullover sweater over black and white plaid shirt, black jeans and black boots.

Option 4: The Cool Guy

Class up your jeans for a big night out or first date with that could-be special someone. Pair dark jeans with a boucle sweater layered over a plaid shirt and black boots for a look that’s not basic but still easy to put together.

Stitch Fix men’s outfit with navy blazer over white plaid button-down shirt, brown jeans and cognac boots.

Option 5: Smart Attire

Trying to bring jeans to the office? Dress up your jeans with a blazer, button-down and dress shoes. You say business casual, we call it a solid outfit for any work event, upscale dinner or sit-down show.

Stitch Fix men's outfit laydown featuring grey jeans, white high-top sneakers, white henley and black hooded flannel.

Option 6: Keeping it Casual

Faded jeans, t-shirt, flannel shirt and sneakers—the go-anywhere-do-anything outfit that has stood the test of time. Perfect for running errands, watching the game, walking the dog or biking around town.

Now that we’ve shown you how jeans really do go with everything, are you ready to add some pairing options for your denim? Take your style quiz, order a Fix and ask your expert stylist for new shirts, layers and even shoes to wear with your jeans. You can try on everything at home and keep only what you like, then send back the rest. Shipping and returns are always free. It’s just that simple.

Style Advice, Anytime

Get expert fashion advice without the expert price.

Get a personal stylist

Get articles and style advice—straight to your feed.

Follow Us