How to Dress Like A Bad Boy: The Ultimate Guide


Who are bad boys? This breed of men has an attitude that says they don’t care about conventions, and they ooze confidence and sex appeal. Girls don’t want to love them but can’t help it, and guys want to be them.

They’re known heartbreakers, but they always seem to find new romance. Their I-don’t-care attitude comes from inside, and they show it off through their clothes. Bad boys don’t just dress anyhow. They wear clothes that naturally reflect their badass nature. 

This article will outline the main components of modern-day bad boy outfits and show you how to dress like a bad boy.


Uppers are a form of clothing for men covering the majority of their chest as well as the upper half of their body, particularly between the neck and their pants or shorts. The lower part of the top may be as short as the mid-torso or as long as the mid-thigh.



Originally only worn as undershirts, t-shirts give off a casual, nonchalant vibe despite their simplicity. Imitating style icons like James Dean and Marlon Brando, you can never go wrong with a bad boy look sporting the classic white tee. Though you can try other colors, stay away from bright ones seeing as they can undermine the laid-back badass look. Stick with plain tees that don’t feature graphic designs. T-shirts give you a relaxed, unconcerned vibe that’s a must-have accessory for the bad boy look.



A turtleneck is one of the best pieces of clothing for the fall and winter seasons, but many people are hesitant to include it in their wardrobe because they don’t know how to rock it. Turtlenecks give you a chic retro badass vibe, which makes you stand out from the crowd. 

Style your turtleneck with a suit! Yes, you read it right. This look exudes power,  so if you want to try something different from the same old shirt inside a suit and tie, this is it. And supposing that you’re new to the world of turtlenecks, try basic and neutral colors until you feel more confident to branch out into more elaborate styles. 

Some of the clothing items you can style with your turtleneck are blazers, denim jackets, suede jackets, flannels, etc. They are bound to get you more attention and make you sound and look sexier. 

Leather Jacket


Every bad boy worth their salt should have a leather jacket in their wardrobe. In particular, black leather jackets give you the quintessential look on their own. They were popular in the 1950s and are still popular today. Try a classic biker jacket or a more modern bomber jacket style. 

You can pair your black leather jacket with a turtleneck top. What you can’t pair with it are wide pants, collared shirts, and anything formal. Keep the rest of your outfit casual and low-key to offset the statement of your jackets. 

Remember that a leather jacket isn’t the only choice for a man who wants to project a bad boy image. Some other suitable options are denim or trucker jackets, but only when the weather is mild. When wearing a denim jacket, try to vary the color and tone, so it differs from your jeans.


From chinos to denim jeans, there are numerous styles of trousers that can be worn for various occasions and provide a refreshing change from traditional pants. You need to know what pants to wear and how to style them, whether you’re going to the workplace or on a date with the flavor of the month. Below are some of the most common fashion trends to consider for your wardrobe.

Denim Jeans


Denim jeans are required for the bad boy look. Corduroys and khakis aren’t going to cut it. Just denim. 

The material is a classic, so they’re a must-have for any wardrobe. It provides a level of sophistication and practicality to any ensemble. Never underestimate a pair of denim jeans. 

Denim comes with impeccable designs and also inspires you to dress well.

Choose your favorites, but make sure the brand you go for is dependable. It’s perfectly acceptable to spend a little more on them because they are well worth it.

The trick to achieving a cool denim look is to keep it simple and not too preppy. Dress appropriately for the occasion. Choose a plain-colored t-shirt to pair with your jeans and shoes. Add a cool pair of shoes to this outfit for the perfect finishing.



Chinos are cotton trousers made of cotton twill fabric or a similar material.  They are a cross between khakis and dress trousers. It’s a common style and a great piece of workwear that has a really cool look to it. If you invest in this, you will savor each moment you wear the pair.

Chinos are versatile and are a step up in a dressy world. They’ve been a part of the fashion world since the twentieth century and come in a variety of styles and designs appropriate for various occasions.  This clothing item confers that air of utter disregard on bad boys.

Pair the chinos with a t-shirt, a denim jacket, and sneakers for semi-formal occasions. When you need to attend a casual business meeting, pair them with a blazer and brogues.



Cargo pants are loose-fitting cotton pants with wide patch pockets halfway down each leg. The pants were originally made for the military in the 1930s and were mostly used for outdoor activities. They’re famous for holding field dressings and have grown in popularity as part of street-style looks over the years. These pants are a great way to finish off a modern outfit as they combine comfort and fitness.

You can pair them with a black t-shirt and a cap to get a fantastic look. A light-colored shirt would also work to make a fashion statement.


Shoes are an essential part of any outfit, seeing as the right footwear can make or break your look in a matter of seconds. So, if you want to look fashionable, you should have the right shoes. Fortunately, this article guides you and your feet in the proper direction. From attending a formal event to running errands, here’s a narrowed-down list of trendy shoes that every bad boy should have in his closet.

Leather Boots


Boots are well suited to a bad boy’s lifestyle and you have options such as combat, Chelsea, and chukka boots to choose from. For a more casual, edgier look, choose an ankle-high black or dark brown boot and cuff your pants. Bad boys always wear black boots because they are cozy, functional and exude a ruggedness that girls adore. They are also ideal for both a hot and sunny day in California and a cold Canadian winter night. 

Suede Chukka


This simple ankle boot features a round toe and two or three lacing eyelets. Its design is traditionally two-paneled and does not contain over-the-top embellishments, allowing the shoe’s texture to speak for itself. Indeed, a tan or cream suede pair of chukkas will complement any wardrobe.

These shoes belong to the more laid-back end of the spectrum, providing an elegant alternative to sneakers. For the best look, match chukkas with a pair of jeans or chinos and a polo shirt. They’re also a safe way to dress down an ensemble in danger of becoming too formal with brogues. You can make your outfit look more approachable by pairing chukkas with denim or a sports jacket.

White Low Top Trainer


You can’t go wrong with a simple pair of white low-top trainers in your bad boy get-up. For a monochromatic look, white low-tops look great with black jeans. When boots or chukkas are too much, a simple pair of white trainers will create a casual but polished look.



Every bad boy wardrobe should have a pair of trendy yet comfortable running sneakers. Choose a style with minimal branding for versatility. For a bold bad boy look, bright colors also work well. 


There are a lot of things that a man can’t have too many of, and socks are one of them. Notorious for getting lost or developing holes, they could portray the refinement or downright snobbishness of the wearer. 

Socks are an easy way to add a chic finishing touch to any bad boy outfit without going overboard. For example, you could choose a high-quality knit in a neutral color to go with fine tailoring or something vibrant and bold to go with a variety of statement-making outfits.

So, if you’re looking for a classic pair or a sock that will fill the gap between the end of the trouser and the footwear, here’s a list of the best socks for bad boys.

Retro Sporty Socks


These are the kind of socks you’d wear on a regular basis. When you’re working out, pair them with gym shorts or even cropped trousers and distressed jeans. The retro sporty vibe is what makes these picks appealing to bad boys, hypebeasts, and average Joes. Tuck your sweatpants in, flaunt them with a cuffed hem, pair them with a ’90s dad sneaker or with your Jordans.

Calf Stripe Socks


Calf stripe socks epitomize the evolution of fashion and come with traditional stripes around the calf. They have stay-up technology that provides the perfect tension level to prevent your socks (and stripes) from slipping.

They have excellent cushioning, just the right amount of compression, and are made of moisture-wicking materials.

No-show Socks


No-show socks are a great style statement. Flaunt those inches of exposed skin between your fashionable ankle grazers and your beautiful shoes. It tells people that you’re fashionable and love living to the fullest.


Although jewelry isn’t needed for a bad boy look, a few cool accessories will help spice up and personalize your outfit. Accessories in reds, dark blues, earthy shades, and leather are your best choice. Silver is also a safe option, but avoid gold.



Band rings have long been symbols of marriage, but that doesn’t mean a bad boy can’t rock one. 

The signet ring is no longer just for toffs and gangsters. It’s back in style and makes a great alternative to a simple band if you want to stand out. They look particularly nice if they’re etched with a family crest, initials, or something meaningful to you.

Otherwise, it’s best to keep it plain and timeless. A sterling silver ring will never go out of style, and it can even be worn with a wedding band of the same material on a different finger.

Stainless Steel Watch


A stainless-steel timepiece is the modest, no-nonsense cousin of the gold watch that will last not only one lifetime but many if passed down through successive generations. 

The material, which was originally used in manufacturing firearms, is both attractive and durable. It looks just as good with a suit and tie as it does with a T-shirt and chinos combo.

Despite the advancement in technology, bad boys would always look to their steel wristwatches for time.

Leather Bracelets


Bracelets are one of the most popular men’s accessories today. Though traditionally associated with women, bad boys now wear them to show that they don’t care about societal conventions.

Leather bracelets are becoming increasingly sexy for either casual or formal looks. They can dramatically change your style or provide the much-needed minor enhancement and personality to round out your outfit. Separately or combined, you can wear these to create a sophisticated look.

Bracelets come in a wide range of types, with leather bracelets being one of the most common, along with solid metal and chain bracelets. Wearing them is a great way for bad boys to express themselves with the many different designs to choose from. 

Leather Belt


A good belt not only keeps your pants in place but also keeps your look together. In particular, a good cowhide belt will last long after other accessories have gone out of style, whether it’s as a much-needed division between the top and bottom halves of an outfit for tall men or as a subtle complement to leather Derbies.

Choose from brown, black, or even better, a combination of the two, and always go for the best you can afford. This thing will be holding your pants up for a long time, and you don’t want to be unseated by a brittle imitation. Subtle, classic buckles in natural metallic tones will also serve you well.



Sunglasses are the ultimate bad boy fashion accessory. Almost everyone wears them regularly and wouldn’t leave the house without them. Your look is immediately transformed when you wear your shades. 

More than just a fashion accessory, sunglasses have long been associated with rebellion, individuality, and personality.

Leather Billfold Wallet


Making payment for your purchase is now as simple as swiping a smartwatch, so it says a lot that the billfold wallet is still a fashionable accessory today. A leather wallet is practical, molded to the contours of its contents, and it ages to perfection.

Many men opt to have their note carriers embossed with their initials. It signals their intention to keep it for the rest of their lives, even if the contents inside don’t make it past the middle of the month.

What to Avoid

No Stripes

Everyone knows nice guys are the ones who wear stripes in vivid, lively, and playful colors. Whether vertical or horizontal stripes, trash them. They definitely announce to the world that you’re a “nice guy.” You’ll be hard-pressed to find a bad boy wearing a striped shirt or one with a variety of bright colors. 

The bad boy persona requires simple-colored clothing like black, blue, maroon, dark grey colors. Anything monochromatic is great, and it can be a polo, a Henley, or any sort of shirt or blouse you want. Plain, clean-cut t-shirts only. 

No to Blue Jeans

Nice guys wear blue jeans. As a bad boy, you should try colors like grey or black jeans. Guys who wear black jeans are automatically seen as bad boys. It’s not rocket science, dark colors just make you more mysterious. Black, being one of the greatest colors of all time, makes you look thinner, more muscular, sexier, and more badass. 

Frequently Asked Questions

What are the best bad boy’s shoes?

Chelsea boots, lace-ups, and chukkas are all perfect choices for bad boy’s dress boots that can pair with a variety of outfits. For less formal occasions particularly, loafers and shoes are excellent options.

How can I pull off denim on denim?

The trick is to make sure the denim pieces aren’t all the same color. If you’re pairing a denim shirt with denim jeans, try a lighter shirt and darker jeans. Note that weathered and worn-in denim shirts always look better. Suede boots are an excellent way to finish things off, and you should feel free to beat the heck out of them as well. The goal is to look simple and rugged.

Are bracelets in style today?

Bracelets are still fashionable, as they were last year and as they will be next year, for a good reason. Bracelets are a simple way to express yourself, your standing, your beliefs, and your sense of style. Several designs, colors, and styles are available, so you’re sure to find a bracelet that matches your bad boy look.

Should socks match my shoes or pants?

Your socks should be the same color as your pants or a shade darker. This creates a continuous visual line from your waist to your shoes. Otherwise, an observer’s gaze would be drawn to your ankle, which is not an area we want to highlight. To match a tie, shirt, or pocket square, use a sock with a secondary color. 

A Final Word From The Trending Man

There’s a marked difference between being a nice guy and a bad boy. Bad boys are rebels who discard conventions and embrace their instincts. Try growing some facial hair, so you don’t look like a nice, decent man but a badass instead. You can also show some skin and expose your forearms to add to the look. Leave the first few buttons of your shirt undone or roll up your sleeves if your body hair is properly groomed. Don’t “overwear” your leather. Make it one item at a time.

The bad boy look is unfailing in its simplicity and ability to make a powerful and difficult-to-forget impression on everyone in the room. To get more ideas for your bad boy aesthetic, look to James Dean, Marlon Brando, Johnny Depp, Ian Somerhalder, and others.

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