20 Baggy Jeans Outfits For Men – How To Wear Baggy Jeans?

Baggy Jeans Outfits For Men. Baggy jeans keep going in and out of fashion. And just when we thought that they were long gone, they are here again. Their comeback brings the perk for men to broaden their style horizons. You might find it hard to style your wide-leg jeans, and that’s normal. The thing is that, unlike other fits, wearing loose-fitting jeans tends to require a bit more strategy.

The return of baggy jeans doesn’t mean you have to change your personal style. That’s gonna be a problem especially if you’re used to wearing regular fits. But consider this a chance to try something out of the ordinary. After all, not everyone can pull off boxy fits stylishly — be one of the few.

What are baggy jeans?

The thing about jeans is that they come in different shades and fit. Baggy jeans, in particular, are not that common among menswear these days. Why is that? For one, the loose fit is kind of outdated as it was only a thing in the 80s and 90s. But what can I say? Old trends are coming into the spotlight again.

What’s so special about baggy jeans?

Baggy jeans give our legs the allowance to breathe more. And some of us find it inconvenient and uncomfy to wear slimmer fits because they’re too tight It has always something to do with the “drape.” By definition, it is how the fabric falls, hangs from and contours to your body. The famous Levi’s 501, for instance, isn’t for all body types. It’s also not that easy to find the “just the right” size for you, especially when buying off the internet.

20 Baggy Jeans Outfits For Men - How To Wear Baggy Jeans?

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Fit is a general style rule, suggesting that stylish outfits must be well-fitting. It happens that baggy jeans are not. So what can we do about it? Well, rules aren’t set in stone. Besides, it won’t hurt you to explore and defy the norm once in a while. Also, loose fits are kind of a trend these days so don’t break a sweat!

But what do you wear with baggy jeans? With a lot of possible outfit combos you could imagine, it’s kinda hard to decide. Luckily, you can narrow down your options with factors like weather, occasion, and mood (yes – you read it right). Here are some additional pointers:

Tips On How to Wear Baggy Jeans

  • Know Your Shade. Jeans come in various colors – black, grey, and blue. The last one comes in different shades – dark washed, and light blue (also known as faded).
20 Baggy Jeans Outfits For Men - How To Wear Baggy Jeans?
  • How Baggy Is Baggy. Baggy jeans give you the leeway to opt for unusual fit. These days, most men tend to wear regular jeans including slim and regular fits. If you want to give baggy jeans shot, make sure they’re not that baggy to the point that it keeps you from walking properly. And you will feel it yourself once you try them on in front of a mirror. It’d also help to walk around and stretch a bit. 
20 Baggy Jeans Outfits For Men - How To Wear Baggy Jeans?
  • Make Smart Choices When Buying Online. Imagine wearing very tight jeans, and you can’t move anymore. That’s awkward right? and not to mention, problematic. The same goes for baggy jeans. Make sure you get the right measurements when buying baggy jeans online.
20 Baggy Jeans Outfits For Men - How To Wear Baggy Jeans?
  • Choose Your Denim. The weather shall be your basis as to which denim type to pick. This fabric is known for its “warming capabilities” so don’t say I didn’t warn you. In summer and spring, have the pants made of lighter denim materials. And of course in winter and autumn, thicker denim suits best.
20 Baggy Jeans Outfits For Men - How To Wear Baggy Jeans?
  • Oversized Tops. You need to balance to get along with how the jeans fit to you. So it’s a great idea to wear slightly bigger tops with your baggy trousers. Steer clear of small and tight outfits as they’d ruin the silhouette.
20 Baggy Jeans Outfits For Men - How To Wear Baggy Jeans?
  • Footwear. As your shoes play a significant role in your style, don’t let the baggy jeans drown them. Opt for chunky designs like boots, sneakers, and skate shoes. Ditch the Oxfords and brogues for now.
20 Baggy Jeans Outfits For Men - How To Wear Baggy Jeans?
  • Accessories. Stand out to accessorize. Borrow some pieces from the same era when baggy jeans came from. Think of pocketchains, for example. They have a certain appeal that makes your outfit asthetic. But don’t go overboard.
20 Baggy Jeans Outfits For Men - How To Wear Baggy Jeans?
  • Show some ankles. Simple style hacks like cuffing the hem would make a big impact. The dilemma of the hem sitting loose on your shoes is common among baggy trousers. You can get more ideas on this from our sockless guide for men.
20 Baggy Jeans Outfits For Men - How To Wear Baggy Jeans?

What To Avoid

  • For Skinny Guys. I would advise scrawny men against wearing baggy jeans. The sole reason is that loose pants tend to make them appear thinner and smaller. Our legs play a big part in creating a good silhouette, and disproportion can get in the way of that. Short guys should steer clear of these trousers as well. Opt for slim, relaxed and regular fits, instead. 
  • For Plus-Size Men. The same goes for men with a large build. Baggy jeans will make you bigger, and you don’t want that. Not that it’s wrong to be big but fashion-wise, men (and women) prefer to look less bigger.
  • In The Office. Jeans aren’t usually a part of the workwear, let alone the baggy fit. But if the company states otherwise, stick to relaxed, regular and slim fits. The same rule applies when attending weddings requiring casual dress code for guests. Save the loose fit for casual wear.
  • Formal Affairs. Jeans don’t belong in the formal setting, let alone baggy fit. Don’t let them see you wearing your wide-leg jeans in black-tie, weddings, and galas.
  • Heavy Fabric. Baggy jeans tend to be bulky because of the extra fabric. But you can still look for slightly lighter types because it’s inconvenient to walk while wearing heavy trousers.
20 Baggy Jeans Outfits For Men - How To Wear Baggy Jeans?

What to Wear With Baggy Jeans?

Since this is a tricky style to pull off, the chances are you’ll be searching for inspiration online – that’s great! See what your favorite models and celebrities are up to. Speaking of which, you might wanna take a look at these outfit ideas on how to wear loose jeans.

20 – With Checkerboard Top

Baggy jeans are a fashion trend in 2022. I think it’s only fitting to pair them with another trend – checkerboard printed top. This sweater is equipped to shield you from undesirable weather elements like cold and rain. Unlike puffer coats and heavy overcoats, a pullover is lightweight so need to worry about it being uncomfy.



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19 – With a Printed Top

Sport your favorite prints and patterns through your tops. Use your outfit to channel and radiate positivity. For instance, florals signify freshness and growth. This is also an opportunity to try new styles, including those made by your favorite designers. Daniel Fletcher is one of my favorites. Go check out his craft to see some inspo.

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18 – Try Ripped Baggy Jeans with Cardigans in Fall

Ripped baggy jeans are the most casual pants I could ever think of. It’s a no-brainer to pair them with casual tops to balance the outfit. These are ripped trousers, but don’t get carried away. Others have large holes, and I hate them. To keep a bit of decency, opt for a subtle variant like this one:

20 Baggy Jeans Outfits For Men - How To Wear Baggy Jeans?

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17 – Try The 90s Style Baggy Jeans Outfit

These pants are naturally shapeless, so crop the legs at the ankle. Your outfits should also balance the boxy fit so opt for bigger hoodies or pullovers. Consider matching your top to your shoes.

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16 – With a Striped Shirt & Denim Jacket

Aesthetic outfits involve elements like stripes, boxy silhouettes, and pastels. Combine them in a single ensemble and you are in for an edgy and avant-garde look! It comes down to your choice of clothing and how you pair them, so you have to be careful. Clashing is a big no-no! Here are some of My Favorite Striped Shirt Styles.

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15 – Wear Vintage Baggy Jeans with a Black Tee & White Jacket

Baggy jeans are a thing from the past. They have a certain aesthetic, suitable to create stylish combos. While it’s not okay to look back, I think we can spare ourselves from the rule for now. Fashion has the magic of making the old trends stylish by adding new touch to them. Look for a faded wash.

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14 – Try Wide-Leg Jeans with Button Down Shirts

These jeans are perfect for men with wide hips and long legs. Seize the chance to sport wide-leg jeans if you have these qualities. 

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13 – Best Shoes To Wear With Baggy Jeans

Look for shoes with bulky designs as they are the best pairs for baggy jeans. Choose from hiking boots, Timberlands, and chunky sneakers.

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12 – Go Weekend Casual with Bright Tops

The rule of thumb with jeans is that the lighter the shade, the more casual they’d look. No need to worry about this as baggy jeans are casual as they are. Try this style on your next weekend gig. Get a bright-colored top like this gold jacket. 

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11 – With a Trench Coat

During the colder months, team up the jeans with overcoats without a second thought. Make sure the trench coat is well-fitting despite the natural length. Failing to do so might result in the outfit drowning you, and no one wants that conundrum.

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10 – With Your College Sweatshirts

What better way to rock your jeans at school? Pair them with a school sweatshirt like this one. And I’m admiring how white makes the trousers pop.

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9 – Try Baggy Skater Jeans with an Open Button Down

They made their way from runway to retail, making them more accessible for fashion lovers like us. Consider cuffing them so you can walk with more comfort.

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8 – With a Baggy Hoodie

Nothing screams streetwear like a nice graffiti print. To fully embrace the trend, get the fanciest hoodie you can find. But if you’re not game for it, stick to plain designs.

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7 – Layer With Your Favorite Suede Jacket

It would be great to pair your baggy jeans with suede and bomber jackets. Opt for brown, tan, and black for best results. Here’s my latest post on styling a suede jacket.

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6 – With a Varsity Jacket & Graphic Tee

Varsity jackets have a natural broad fit, making them suitable to pair with baggy jeans. Here are some more ways to wear your varsity jacket.

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5 – With Knitwear in Winters

A cozy, knitted sweater could be a good substitute for your hoodies and jackets. Knitwear tends to be lightweight despite having the power to protect you from cold. Wear this outfit at home, or when going out for casual errands.

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4 – With Flannel Shirts

Sport a lumberjack look with the flannel-and-baggy jeans combo. Look for subtle flannel designs like checks in primary colors so you can also pair them with other pants.

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3 – With A Polo Shirt

Look for baggy jeans with a cropped hem. Team them up with a long-sleeved polo shirt, probably one with stripes. This could be your school outfit. Here are some more ideas on how to wear your polo shirts this year.

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2 – With Oversized Basic Tee

Choose jeans with a cropped hem so there’s a sharpness that comes with a streamlined look. Thrift stores have a lot of good vintage and graphic tees. Another option: get designs of your choice from the internet and get them customized in printing stores.

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1 – Try a Camping Outfit with Puffer Jacket

Camping entails the challenges brought by terrain and woods. Opt for functional clothes like a fleece hoodie, and then wear a gilet over it. Boots are essential especially if you are hiking.

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Frequently Asked Questions

Q. Is denim-on-denim in style?

No. This is also known as the Canadian tuxedo, and it’s a faux pas. You might see some fashionistas wearing this, and don’t mind them. You can try the outfit if it looks good on you. But personally, I think denim tops shouldn’t go with denim trousers. Something’s really off with the outfit, even if you combine two different shades.

Q. What should I wear with baggy jeans?

Wear them with casual and streetwear clothes. Don’t team up your baggy jeans with a formal piece like a tux. An unstructured coat is fine, however.

Q. What looks best with baggy jeans?

Check your closet and look for wardrobe staples. Basically, anything can go with baggy jeans – from basic tees to sweaters. I suggest you wear your baggy jeans in winter so you can pair them with outerwear like trench coats, for example. Loose-fit jeans look better with big and slightly oversized tops.

Q. What's the best type of denim?

Selvage (also selvedge) denim is your first option. But this denim variant is more expensive. And if you can’t find any, look for cotton.

Q. Can I wear baggy jeans with blazers?

Yes. A blazer doesn’t look so good with skinny jeans. It doesn’t work with the too baggy fit, either. So look for slightly loose jeans, and this can be your smart-casual attire. This outfit is suitable for a corporate setting that allows jeans for a dress code. Make sure to wear dress shoes and not sneakers or anything casual.

Q. Where To Buy Baggy Jeans

Jeans have long been a wardrobe staple for both men and women. They are versatile enough to pair any outfit you already have. That makes them worth investing in. Unfortunately, getting a pair of jeans doesn’t come in handy. There are a few things you have to consider, including the fit, the shade, the fabric and the brand. Though the last one’s a joke.

If you have a favorite clothing brand, stick to it. I believe it didn’t become your favorite for anything. But first things first, make sure the products are of good quality otherwise don’t buy them. Next, get the perfect baggy jeans for your body type and style preference. Check Nordstrom and Amazon if you’re buying online. Here are my personal picks:



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