Baggy Jeans for Men are Back: Here’s How to Wear Them

Time to make the leap?

It’s official. After years of threatening to make their return, baggy jeans are back.

What started a few years ago with a gradual loosening of the fit around the leg (everyone remembers drop-crotch jeans, right?) has now morphed into full-on 90s-style skater pants. It’s a look that has moved from being pretty much runway exclusive, to one that can now be easily found on any high street and online fashion outlet.

As with any relatively recent trend, adopting it for the first time is a challenge—especially when the change is as extreme moving away from skinny denim. We’re here to answer all your questions about wide-leg jeans, as well as show you nine baggy jeans outfits for inspiration.

Read more: Here is a list of the best baggy jeans for men you can currently buy

How to Style Wide Leg Jeans (The Answer is Balance)

The biggest risk with wide denim is having the jeans drown the rest of the outfit. If this happens, you’ll lose all your shape and suffocate your style. You have to be extra careful with the fit, as well as the clothes you wear with your new jeans. Here are five rules to keep in mind.

  1. Your upper half should typically be broad or oversized to balance the wide-fitting jeans. Think hoodies or bomber jackets rather than tight t-shirts.
  2. The best shoes to wear with baggy jeans are chunky styles like boots, sneakers, or skate shoes. Slimmer shoes risk being overwhelmed by the material and causing the outfit to look out of balance.
  3. Go wide, but not long. Give your outfit some shape by ensuring the jeans are cut so they fall either just touching or just above your shoes. If your jeans are too long, turn them up.
  4. Many of the jeans on this list are heavily distressed. Don’t shy away from worn denim or tears.
  5. Keep the outfits casual. Slimmer-fitting jeans are still best for the office or formal occasions.

What to Wear With Baggy Jeans?

The best items to wear with baggy jeans are oversized sweaters, t-shirts, and jackets. By going for a larger fit, you balance out the size of the jeans, which brings an element of symmetry to the outfit.

I’d definitely avoid wearing tight-fitting clothing with baggy jeans as the contrast between the two pieces will be too much.

Nine Baggy Jeans Outfits For Inspiration

Next up, I’ll run through nine outfits that show you how to wear wide-leg jeans. I explain why each ensemble works so you can use the tips to inspire your own fits.

Outfit One: With a Chunky Coat and Boots

Wide fitting jeans brown coat

Why it Works: I love this outfit because it keeps everything so chunky, which balances out the wide jeans. The wool coat is very square, which accentuates the shoulders, while the thick boots more than hold their own. The knit bag is the perfect accessory.

Outfit Two: With an Oversized T-Shirt

ASOS Studios

Why it Works: The main issue with baggy denim is its shapelessness. It risks drowning the wearer. In the above outfit, this was balanced out with thicker, boxy coats and sneakers. Another way to add shape is to crop the legs at the ankle. This way, you still get a tailored look despite the wide leg. The jeans in the image above from Asos pull this off really well.

Outfit Three: Leather Bomber Jacket

Why it Works: The bomber jacket is a great style to wear with wide-leg jeans as it has a natural broad fit. The strength of the jacket also means the jeans don’t dominate the look too much. I love how the colors of the canvas shoes match the rest of this outfit and the pocket chain is a cool flashback to the 90s.

Outfit Four: Baggy Jeans With Sneakers and Turtleneck

Light green jeans and green coat

I love this outfit because the mint green color of the jeans is so unusual. But, it looks amazing with the green coat, while the off-white turtleneck finishes the look really nicely. As with other fits in this article, the cuffed pants ensure they don’t overwhelm the sneakers.

The brown bag is a nice addition too. I personally think shoulder bags look much better than alternatives like backpacks when worn with a wool coat.

Outfit Five: Baggy Jeans With a Chunky Sweater

Why it Works: A chunky sweater is the perfect item to wear with baggy denim. While a thinner jumper sees you risk having a bottom-heavy silhouette, thicker material on top keeps a better balance. I particularly like the turnups on the jeans in this image as it keeps the shape sharp while showing off the shoes. These are by far the most formal shoes on this list, but they definitely work.

The Boardwalk Style Tip 👇

The above outfit proves that it’s ok to wear smart shoes with jeans. The easiest way to make it work is to choose dark unfaded denim that fit you well. Find out more about wearing dress shoes with jeans here.

Outfit Six: With Sportswear


Why it Works: Pairing your baggy denim with sportswear creates a 90s Britpop vibe. The darker denim in the image above is cut perfectly to just brush the top of the shoes, stopping them from being drowned in denim. Wear an oversized, bright t-shirt under the jacket to continue the streetwear vibe inside.

What Type Of Jacket Goes With Wide Leg Jeans? 👇

Sportswear jackets are a great fit for baggy jeans because the casual loose style matches that of the denim. But most casual loose-fitting jackets will do the trick, including my personal favorite, the denim jacket. Just look at what’s in your wardrobe and experiment to see what works.

Outfit Seven: Baggy Double Denim

Why it Works: Only the truly brave are ready to step out in baggy denim jacket with jeans. If you pull it off, you may end up with something like the fit above. It works well because the colors are different enough to add contrast to the outfit, while the shoes, cap, and t-shirt add variety to the look.

The Boardwalk Style Tip 👇

This is a great example of a monochrome outfit (at least, barring the shoes). As well as the pants and jacket, the hat and socks are both in differing yet complementary shades of blue. This means the entire look is very easy on the eye. Consider looking for ways to wear different shades of the same color in your next outfit.

Outfit Eight: With Skate Shoes and a Hoody


Why it Works: If I’m being honest, this outfit should probably be first on the list. Wearing baggy jeans with a hoody and skate shoes is the classic way to style this type of denim. The light wash of the jeans in the image goes really well with the white oversized top. Meanwhile, the torn denim continues the punky, skater look. The bucket hat is absolutely the icing on the cake.

Outfit Nine: With a Casual Shirt and Sneakers

Wide Light Blue Jeans

There are several reasons why I like this outfit. First is that the light color of the sneakers and casual shirt go well with the light blue jeans. The jeans are also rolled up at the hem which ensures that while still baggy, the outfit doesn’t look sloppy.

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Duncan Elder

Duncan is the founder and editor-in-chief of The Boardwalk. He's a menswear writer who has spent the last 15 years developing his own sense of style, which lies at the cross-section of mid-noughties indie and Uniqlo-inspired minimalism.

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