10 Ways to Style Men’s Baggy Jeans
Baggy Jeans are finally back in style, and they are once again becoming one of the most popular pieces in men’s fashion. And personally, I am very excited about it! There are so many different styles to choose from in fashion, but the amazing thing about baggy jeans is that you can almost mix and match them with any kind of style. In this simple but informational guide, I will personally break down how to style men’s baggy jeans that you can wear in any season, any body type, and aesthetic. All the way from simple styles and outfits, all the way to elevated layered outfits. You will find 10 easy formulas you can copy, customize, and make your own.
Considering a Change
If you are new to streetwear and not familiar with this style, it does not mean you need to change it. But possibly consider trying something different. Not everyone will be able to pull off these unique outfits.
What are Baggy Jeans?
Baggy jeans are denim pants with a loose, relaxed fit that gives you extra room in the legs. They’re a modern take on 90s style and have become popular again because they’re comfortable and easy to wear. If you want to learn how to style men’s baggy jeans, it helps to know what makes them different. Baggy jeans usually have a straight or wide leg that sits perfectly over the shoe, giving it a stylish look and feel.
Finding the Right Size
Be Careful When Purchasing Online- Especially when you’re first getting into finding the right baggy jeans. Running into problems with sizing can be an issue. Most stores/outlets have different types of sizing for styling their men’s baggy jeans. I personally have run into this issue. I recommend going into different stores and trying them on in person. It will be much easier in the long run, and you will know what size/sizes fit you the best.
Look at Reviews- When purchasing men’s baggy jeans online, I recommend reading over reviews. People who have personally purchased the items will talk about whether the jeans run big/small, and if you should make sure to size up or down. This will give you more information before you continue with your purchase. Some customers will also leave pictures of themselves personally wearing the jeans and note what size they got compared to their height.
Read the Description– When looking at a style of jeans on a website, most companies will have a description if you scroll under the jeans, which will have a size chart and the height and size the model is wearing in the picture. Using this can help you determine which size to get if you’re purchasing baggy jeans online. Doing this has personally helped me make the right choice when buying jeans online.
10 Ways on How to Style Men's Baggy Jeans
You have finally made it to the section where I will be breaking down several different ways on how to style men’s baggy jeans. I will break it into two different sections, where I will show how to style baggy jeans in the winter/fall and how to style them in the summer/warmer season. This section will give you an idea of how you can copy or mix and match these outfits. Stay tuned for the end, where I will add a very important bonus section!
Winter/Fall Inspo
10- With a Stylish Flannel
Pairing men’s baggy jeans with a flannel is an easy go-to for beginners. It’s perfect for the fall or winter season. It’s honestly still a go-to for me.
9- With a Leather Jacket
If you own a leather jacket, you can perfectly pair it with some baggy jeans. This is a perfect combination for the winter or fall season thats also stylish.
8- With your School/Teams Hoodie
Throwing on your school’s or favorite sports team’s hoodie is another option to style your baggy jeans. You can find these kinds of hoodies at thrift stores or pick one up from your local clothing stores.
7-With a Zip-Up Jacket
A zip-up jacket pairs great with baggy jeans because it adds structure to the relaxed fit. Choose a fitted or regular zip-up to balance the outfit, and stick to simple colors like black or gray. Finish the look with casual sneakers or Timberlands for a fresh style.
6- With Multiple Layers
If you’re looking to style baggy jeans with multiple layers, it is an easy option. Baggy jeans work well with a T-shirt, hoodie, and a jacket on top. The relaxed fit keeps the outfit comfortable, and sticking to similar colors helps everything look put together.
Summer/Spring Inspo
5- With Cropped T-Shirt
A cropped T-shirt is a great way to balance the loose fit of baggy jeans. The shorter top creates a cleaner shape and makes the jeans stand out more. This look works well for casual streetwear and is easy to style.
4- With a Sports Jersey
A sports jersey pairs really well with baggy jeans for a laid-back, sporty look. The relaxed fit of both pieces makes the outfit comfortable and easy to wear. Add sneakers to finish the outfit and keep the athletic vibe.
3-With a Cropped T-Shirt
A cropped T-shirt works great with baggy jeans because the shorter top balances the loose fit. It gives your outfit a clean shape and makes the jeans stand out more. Pair this look with simple sneakers for an easy streetwear style.
2- With a Button Up Shirt
Wearing baggy jeans with a button-up shirt and dress shoes gives you a clean, slightly dressed-up look. The shirt makes the outfit feel more put together, and the dress shoes add a nice touch without being too fancy.
1- With a Graphic T-Shirt
A graphic t-shirt is an easy match with baggy jeans and gives your outfit a cool, 90s-inspired vibe. The relaxed tee works well with the loose jeans, and the graphic adds personality without trying too hard.
Bonus Section- How to Style Men’s Baggy Jeans with Shoes(3 Styles)
Now that I have gone over different ways you can mix and match your baggy jeans with different styles or outfits, you might be asking what shoes to wear. Personally, this was tricky for me. At the end of the day, it’s all preference, but hopefully, in this section, I can give you some great tips on how to style men’s baggy jeans with the perfect pair of shoes!
3 Different Shoes to Pair with Baggy Jeans
3- Simple Pair of White Shoes
A pair of clean white shoes goes perfectly with baggy jeans. They keep the outfit looking fresh and balanced without pulling attention away from the jeans. This combo works with almost any top and is one of the easiest ways to style baggy jeans for everyday wear.
2- Dress Shoes (Loafers)
Loafers add a clean, dressed-up touch to baggy jeans without making the outfit feel too formal. They work best with a straight or slightly wide leg that doesn’t bunch too much at the bottom. Pair this combo with a button-up, polo, or simple sweater for a relaxed but polished look.
1- Black Pair of Shoes
Basic black shoes go great with baggy jeans and make putting an outfit together super easy. The dark color keeps the look clean, and the simple design works with almost any top. It’s an effortless, everyday combo you can wear anywhere.
Not Sure what Outfits Fit your Style? Try this Quiz!
Which Baggy Jeans Outfit Fits Your Style?
Answer a few quick questions to get an outfit idea on how to style men's baggy jeans.
1. How would you describe your style?
2. Where are you wearing your baggy jeans?
3. What shoes do you like most?
Now It’s Your Turn to Style the Look
Learning how to style men’s baggy jeans doesn’t have to be complicated. With the right tops, layers, and shoes, you can create outfits for any season or occasion. Use these styling tips and outfit examples to build looks that fit your personal style and make baggy jeans a regular part of your wardrobe. If you’re wondering where you can find these styles here is a post where I go over the top streetwear clothing brands to shop right now. Drop a comment below and let me know your thoughts and what kind of baggy jeans you will be styling this year!

Hi, I’m Brendan — the creator of Trendy Fashion Streetwear. I love sharing style tips, brand guides, and fashion ideas to help beginners find their own streetwear look.












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