Updated by Ben Chuang

Life isn't easy as a young man, but dressing well is an art that every man can master with the right guidance. Whether you're aiming for a classic, business casual, or casual look, finding clothes that fit well is the key to looking sharp and put together. In fact, scientific studies show that your clothing is a direct expression of your personality and self esteem.

In this article, we'll delve into the essential elements of a man's wardrobe and offer valuable style advice on how to achieve a polished appearance in any setting.

In an era where personal expression through fashion is celebrated, dressing like a man recognizes the importance of striking a balance between individual style and timeless sophistication, no matter which male body type you are.

This article is more than a mere style manual; it's a roadmap to help men of all ages and walks of life cultivate a wardrobe that aligns with their personalities while adhering to the principles of classic elegance.

So, buckle up for a journey through the intricacies of men's fashion, where we'll explore everything from the perfect fit of pants to the subtle nuances that distinguish casual from polished, ensuring that every man can confidently navigate the world of style with authenticity and grace. Don't forget to check out our article on best t-shirts for skinny guys, and what is looksmaxing.

Wearing Clothes that Fit Well

Achieving a polished and put-together look for men begins with the fundamental principle of wearing clothes that fit well. The right fit enhances your silhouette, boosts confidence, and communicates a refined sense of style. Here's a guide on how to ensure your wardrobe is tailored to perfection:

1. Know Your Measurements: Before you embark on a shopping spree, it's crucial to know your measurements. You don't have to become a menswear designer, but get familiar with your chest, waist measurement, hip measurement, and inseam measurements. This knowledge will serve as your compass when selecting clothing.

2. Seek Tailored Silhouettes: Opt for clothing with a tailored silhouette. Whether it's dress shirts, blazers, or trousers, a cut that skims the body without being overly tight or loose creates a sophisticated look. Tailoring can further refine the fit of off-the-rack items to suit your unique body shape.

3. Pay Attention to Sleeve and Pant Lengths: Sleeves that end at the base of your thumb and pants that graze the tops of your shoes are indicators of a proper fit. Avoid overly long or short sleeves and pants, as these can disrupt the overall harmony of your outfit.

4. Mind the Shoulder Seams: The shoulder seam of a shirt or jacket should align with the outer edge of your shoulder. Ill-fitting shoulders can throw off the entire look, so ensure that this aspect is on point for a sharp appearance.

5. Consider the Waistline: Whether it's trousers or jeans, the waistline should sit comfortably at your natural waist without being too tight or sagging. Belts can help fine-tune the fit, but the waistband itself should provide a secure and comfortable fit without you relying on the belt loops. Here is a guide on the different types of belts.

6. Experiment with Styles: Different styles may fit differently, so be open to experimenting. For instance, slim-fit shirts may complement some body types, while others may prefer a classic fit. Finding what suits you best involves a bit of trial and error.

7. Check Your Posture: Stand and sit naturally when trying on clothes. Your posture can influence how a garment hangs on your body. Ensure that clothes look good both when you're standing upright and when you're in a relaxed position.

Remember, the key to dressing well is not just following fashion trends but understanding how to make those trends work for your body.

With these tips in mind, you'll be well on your way to mastering the art of wearing clothes that fit well and exude timeless style. 

Wear a Suit Jacket that Fits Well

Ensuring that a suit jacket fits well is crucial for achieving a polished and sophisticated look. Here are key aspects to consider when checking the fit of a men's suit jacket:

1. Shoulder Fit: The shoulder seam of the jacket should align with the outer edge of your shoulder. If the shoulder seams hang over or fall short, the jacket is not the right fit. Properly fitting shoulders provide structure to the jacket and contribute to an overall sharp appearance.

2. Chest Fit: The jacket should close comfortably without pulling or gaping. Fasten the top button, and check for any strain or excessive looseness across the chest. A well-fitted jacket will allow for a slight pull without creating visible wrinkles or tension.

3. Collar and Neck Area: The collar of the jacket should sit flat against the back of your neck without any gaps. If there's a noticeable gap or if the collar feels too tight, the jacket may not be the right size.

4. Sleeve Length: The sleeves should reach just above the base of your thumb when your arms are relaxed at your sides. A quarter to a half inch of shirt cuff should be visible. Too short or too long sleeves can create an unbalanced look.

5. Jacket Length: The jacket length is crucial for proportion. It should cover your seat and end around the knuckles of your closed fist. If the jacket is too short or too long, it can throw off the balance of the entire ensemble.

6. Waist Suppression: A well-fitted suit jacket often has a slightly suppressed waist, meaning it tapers in slightly at the midsection to create a defined silhouette. However, it shouldn't be so tight that it creates pulling or wrinkles around the button.

7. Vent Alignment: If the jacket has vents, they should lie flat and not pull open when you're standing still. Additionally, the vents should align with the center of your back.

8. Buttoning Comfort: When the jacket is buttoned, it should feel comfortable and allow for natural movement. If there's excessive pulling or the buttons seem strained, the jacket may be too tight.

9. Fabric Drape: The fabric should drape smoothly over your chest and shoulders. Wrinkles or ripples may indicate that the jacket is either too tight or too loose.

By paying attention to these details, you can confidently assess whether a suit jacket fits well and, if needed, make informed decisions about alterations to ensure a stylish and comfortable appearance. For more details, refer to our article on how a suit jacket should fit, or try out our online suit size calculator. 

Wear a Dress Shirt with the Right Fit

Achieving the right fit with a dress shirt is essential for a polished and comfortable look. Here's a guide on how dress shirts should ideally fit on men:

1. Collar Fit: The collar should fit comfortably around your neck without being too tight or too loose. You should be able to fit two fingers comfortably between your neck and the collar when it's buttoned. Ensure that the collar lies flat against your neck without any noticeable gaps.

2. Shoulder Seams: The shoulder seams of the shirt should align with the outer edges of your shoulders. If the seams fall too far down your arm or if they're too close to your neck, the shirt may be the wrong size.

3. Sleeve Length: The sleeves should reach just past your wrist bone when your arms are relaxed at your sides. The ideal length allows for a quarter to a half inch of cuff to show when wearing a suit jacket.

4. Cuff Fit: The cuffs should wrap snugly around your wrist without being too tight. A well-fitted cuff will allow you to comfortably slide your hand through but should not slide up and down your arm without resistance.

5. Chest and Torso Fit: The shirt should fit close to the body without being overly tight. When buttoned, you should be able to move comfortably without excessive pulling or stretching across the chest or midsection. There should be enough room to pinch about 1-2 inches of fabric on either side of your chest.

6. Length: The shirttail should be long enough to stay tucked in when you raise your arms, but not so long that it bunches up when tucked into your trousers. The hem should ideally reach the midpoint of your fly when untucked.

7. Movement Comfort: Test the shirt's comfort by raising your arms, bending, and reaching. The fit should allow for natural movement without feeling constricting.

By paying attention to these details, you can confidently select dress shirts that complement your body shape and provide both style and comfort for various occasions. Refer to our article on how a dress shirt should fit for more information.

Wardrobe Essentials Every Man Should Own

Style and Dress Yourself with Intention

Clothes have a purpose and as an adult you need to be able to communicate that through your wardrobe. As easy as it is to just wear a graphic T-shirt and old jeans everyday, what it comes down to is intention. If you’re dressing yourself with no care or attention, it becomes the same way as when you were 5 years old letting your parents pick out all your clothes for you. 

As an adult you have to be able to take care of yourself and start dressing well. If you want to be taken seriously as a mature adult, then you can easily showcase that in your clothes.

Once you can master dressing with intent, then it can become part of your everyday routine and everyday after, dressing yourself will become more meaningful. You’ll be able to face your purpose for the day and start it with the right foot forward.

This also means investing in pieces that look good on you, rather than ones from decades ago. A well-fitted basic t-shirt with a pair of jeans can look more classy than your old high school PE shirt with the nicest shoes. Take a look at Nimble’s collection of t-shirts to up your wardrobe game in the basics department. 

 

Own a Quality Watch

This tip is more so for those who are interested in making watches a part of their accessory collection. Watches can be a great way to elevate your outfit and overall vibe. Here's a guide on how to wear a watch properly.

They’re classic, aesthetically pleasing, and can be extremely personal. Some personalized or luxury watches can even be passed down through your family for generations.

Regardless, the watch should fit you. Something loose makes your wrist look dainty and something too tight is just plain uncomfortable. Take the steps to find a watch you love and then get it sized for your wrist. These are favorite watches for smaller wrists.

Wear Your Confidence

This may mean different things for different people, but what we’re trying to say is to find a style of men's clothes that makes you feel powerful and confident.

You want to be able to walk into a meeting at work and stand out, in an appropriate way, of course. Blending in with the crowd just doesn’t help you when you’re trying to move up the chain of command.

It’s important to keep reminding yourself of what you’re trying to accomplish. You can’t only think like the people at the top, you have to emulate them as well through their wardrobe.

Sure, you won’t be able to afford everything, but with enough determination and budgeting savvy, it’s possible to achieve similar looks. Don’t be afraid of being bold, even if you have to work up to it. Confidence in yourself is everything.  

 

 Own Jeans that Fit and Flatter You

Blue jeans are classic and overall staples in the world of men's clothing. Which makes it important to have jeans that fit and flatter your legs and hips. Investing in jeans that accomplish this, are well worth the high price tags.

Wearing the right fit of jeans can elevate your casual outfits by a lot. It takes you from a managing teenager to a mature adult. Try finding dark, raw denim that can distress and fade over time as you continuously wear them. Jeans that can reflect their journey with you. Adding to the meaningfulness of dressing yourself every morning.   

When it comes to choosing jeans for men, the key is finding a style that complements your body type and aligns with the occasion. Here's a guide to help you navigate the world of men's jeans, striking a balance between traditional style and contemporary trends:

1. Classic Styles for Timeless Appeal: Opt for classic styles like straight-leg or slim-fit jeans for a timeless and versatile look. These styles work well in both casual and semi-casual settings, making them suitable for a wide range of occasions.

2. Avoid Baggy Pants: This may sound familiar to advice you've heard as a young man, but steer clear of overly baggy jeans regardless of your body type, as they tend to create a sloppy and dated appearance. Instead, choose a fit that follows the natural lines of your body without excess fabric.

3. Versatility of Skinny Jeans: Skinny jeans are a big part of men's clothing and can be incorporated into a modern, casual wardrobe, but the key is balance. Pair them with a well-fitted shirt and dress boots for a sleek and stylish ensemble.

4. 

5. Casual Clothes and Denim: Jeans are inherently casual, making them a staple in any casual wardrobe. Pair them with a plain t-shirt, button-downs, or even polo shirts for a laid-back yet put-together look.

6. Dress Boots for Elevated Style: Elevate your outfit by pairing jeans with dress boots. This combination strikes a balance between casual and polished, making it suitable for a night out or a smart-casual dress code.

7. Avoid Flip Flops in Business Settings: While jeans are versatile, it's crucial to consider the overall dress code. Avoid pairing jeans with flip flops in professional or business settings, as this may appear too casual for the professional environments.

8. Business Clothing Integration: To incorporate jeans into a business setting, choose a dark, well-fitted pair and pair jeans with a collared shirt and dress shoes. This creates a smart-casual look that is both polished and office-appropriate.

9. Male Wardrobe Staples: Consider jeans as a staple in your male wardrobe, ensuring you have a couple of well-fitted pairs in different washes to cater to various occasions.

10. Dress Like a Professional: When dressing for a business environment, ensure that your entire outfit, including your choice of jeans, reflects professionalism. Opt for a clean, well-ironed shirt and polished shoes to maintain a sophisticated appearance.

In summary, the key to wearing jeans successfully lies in choosing classic styles that fit well and align with the formality of the occasion. Whether you opt for straight-leg, slim-fit, or even skinny jeans, pair them thoughtfully with appropriate footwear and tops to create a cohesive and stylish look.

Striking the right balance between classic style and modern trends allows you to navigate the diverse settings of the business world with confidence and flair.

 

 Don't be Afraid of Wearing Color

For some reason, men feel intimidated by anything that isn’t black, navy, or grey. Dark colors have a wonderful neutrality about them, making it able to mix anything with them.

The problem lies in having these colors in your closet, only. Indulging in other colors may feel uncomfortable if you aren’t used to it, but trust us when we say that adding colors to your closet can elevate some of your outfits.

Don’t be afraid of greens, red or maroon, and various shades of blues. When it comes to color, less can help you a long way. You don’t need to have a rainbow array of shirts and button ups, unless that’s your aesthetic, but color accents like pocket squares in suits, socks, and vests can help break up the monotony of a dark and drab closet.  

  

 

Own Effective Outerwear

Unless you live on top of the equator, then it’s more likely that it can get cold wherever you are. It’s important to combat this with appropriate and effective outwear. This can change depending on where you reside.

If you’re experiencing a Los Angeles winter, then you won’t need something too heavy duty. You can utilize bomber jackets and jean jackets. If you experience snowy winters where the temperature can drop giving mind-numbingly coldness, then you might have already invested in outerwear that does the job. 

Owning clothes for every type of season and weather occurrence, is part of taking good care of yourself. In return, you appear as an adult who knows that being prepared for the elements of mother nature is just as important as dressing up for an important meeting. If you don’t have proper outerwear attire, then do yourself a favor and buy some.   

 

Declutter Your Wardrobe

Like Marie Kondo says, “Hold the item and if it doesn’t bring you joy then it’s time to say goodbye.” Sometimes life can just get ahead of you and before you know it you have a closet filled to the brim with clothes that you haven’t worn in years.

To make space for all the new purchases, go through your closet and filter out all the pieces that haven’t seen the light of day since college graduation. 

This isn’t just to clean out your closet, it’s also a meditative process. Clearing out the clutter helps to clear out your mind. It also becomes a journey with yourself and the clothes you’ve used throughout the years that have all been a part of expressing yourself to the world.

Whether that was your intention or not. Once you’ve finished, not only will you have room in your closet, but you will also know that everything in your closet you absolutely love. 

Keep Your Underwear Drawer Simple

Just like you need to clear out that closet, be sure to do the same to your underwear drawer. We know very well how underwear drawers can sometimes be an abyss for socks to get lost into. Keeping things tidy is part of being an adult and we understand that some things will inevitably be forsaken.

Help the future you out by cleaning up that underwear drawer and doing the same process you used against decluttering your closet. Clearly lay out the comfortable underwear and socks you use and filter out the unpaired socks and holey boxers. 

 Don’t be Afraid to Experiment

Sometimes you just won’t know what you like until you try it. Don’t be afraid to explore different patterns, shoes, and types of shirts and pants as you go through this journey. We understand that being bold and going out of your comfort zone can be scary. It’s supposed to be.

Sometimes, by going the extra mile and trying something new is the only way we can achieve optimal self-love and confidence. Just remember that you are your own worst critic and anybody else that has judgement doesn’t really matter in the long run. Experiment because it’s good for your soul and you deserve it!  

 

 

Dress Appropriately for the Occasion

To dress for an occasion means to know the difference between casual formal and black tie on a wedding invite. Being able to know which outfits to where to what is helpful knowledge when you’re navigating the adult world.

Yet, this isn’t just for yourself and your appearance, but for the people you love who are inviting you to their wedding or party. Knowing what’s appropriate to wear and what isn’t is just common courtesy. 

In case you aren’t sure, always consult the all knowing tool that is Google. Casual formal means you don’t need to wear a fine suit, but something with a collar, some nice pants, and stylish shoes could be enough.

Pair it off with an unlined blazer and there you have it. Of course, formal means suit and black tie equals tuxedo. Since black tie is more uncommon you should have formal and casual formal outfits already hanging in your closet.    

 

 

 

 Keep Developing Your Style

With that being said, keep getting to know yourself and see what styles excite you and boost your confidence from casual celebratory events to important funeral outfits for men. Clear out your closet, fill it with things that make you feel like a man, and go be your best self.

Experiment and keep fine tuning the styles that work for you. Don’t be afraid of the judgements of other people. As Dr. Seuss once said, “Those who mind, don’t matter and those who matter, don’t mind.” Fashion isn’t about keeping up with trends, it’s about exploring and expressing your true self to the world. We understand that this process is a journey, but know that everyone is rooting for you! 

Frequently Asked Questions About Dressing Like a Man

How to Wear Clothes Like a Man:

Dressing like a man involves understanding your body type and selecting clothes that flatter your silhouette. Embrace classic styles like a well-fitted collared shirt paired with tailored wool trousers or a nice suit. Incorporate high-quality pieces that withstand trends, like a light blue button-down shirt or a versatile pocket square.

To add a modern touch, consider white sneakers or a baseball cap. Step out of your comfort zone by exploring menswear designers for inspiration, and soon you'll master the art of dressing like a confident and stylish man.

How to Dress Like a Man as a Woman:

Dressing like a man as a woman is about embracing a style that reflects strength and confidence while maintaining a touch of femininity. Start by incorporating menswear-inspired pieces, such as tailored blazers, button-down shirts, or trousers, into your wardrobe.

Consider a nice suit with a feminine cut or experiment with oversized silhouettes that mimic a more masculine aesthetic. Don't be afraid to play with accessories or add a bold lipstick to balance the look. By blending masculine and feminine elements, you can create a unique and empowering style that allows you to dress like a man while staying true to your identity.

How to Dress to Look Like a Boy:

To dress to look like a boy, start by opting for more relaxed and youthful styles. Consider comfortable and casual pieces like a quality pair of white sneakers paired with jeans or shorts. Experiment with oversized T-shirts or sweatshirts, and add a baseball cap or one of these best beanies for men for a laid-back vibe.

Embrace clothing items with a sporty or streetwear influence, and don't shy away from mixing patterns or layering. Whether you're exploring menswear or adding a touch of androgyny to your wardrobe, dressing to look like a boy allows for a playful and carefree expression of style.

How to Dress Like a Mature Man:

Dressing like a mature man involves refining your wardrobe with timeless pieces that exude sophistication. Invest in high-quality garments, such as a well-tailored suit or a nice pair of wool trousers. Embrace classic colors like navy blue, and consider collared shirts or polos for a polished look.

During the winter months, opt for a warm coat in neutral tones. Incorporate accessories like a leather belt or pocket square to elevate your style. Step away from overly casual attire, and focus on good quality, well-fitted clothing that reflects a more refined and mature demeanor.

For more, check out our guide on how to dress more masculine.