How to Dress Like a Man

Daniel Bishop
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First Things First

Shop for the Right Clothes

Get rid of any baggy, homemade, or otherwise ill-fitting clothing. Okay, now onto how to dress like a man. You should wear clothes that fit in all the right places. Remember you can always go to a tailor to have your clothes tailored to fit you properly.

Fitting and basic clothing is the best way to dress like a man. Men look good in clothes that fit well and complement their body type.

Avoid the temptation of wearing an ill-fitting suit and just wearing an ill-fitting shirt or pants too small for you. You should spend the money and make sure you're wearing clothes that fit well.

Next, you should have a basic clothes cabinet where you can get dressed quickly. This way you'll always have something to wear when you throw on a suit.

Keep it Simple

If you're not sure what to wear with what, start with the foundation, and then build from there. Start with a pair of solid bottoms, and an ironed shirt. From there, you can add a jacket, or a blazer, a tie, a sweater, etc.

If you're not sure of your measurements, buy clothes that are slightly too big (there's no such thing as a "slim fit" dress shirt, after all), in neutral colors like black, white, gray, and navy. Stripes are a riskier option, but not entirely unwearable–just be sure to keep them narrow. If you know your right trouser is shorter than your left, or your sleeves are longer, deal with it. Those are just the idiosyncrasies of your body, and you're going to find that once you start wearing properly-fitted clothes, you'll really start to see a difference.

When it comes to new clothes, if you want to add stripes, pick a shirt that's one or two sizes too big (so the shirt drapes properly when it's untucked), and wear it with the intention to tuck it in. Which leads us to…

Charcoal Suit

Charcoal suits are a very handsome item because they are a nice break from the common dark suits you see everywhere. Charcoal suits have a very professional look to them, but they also give you a more casual look, which makes them great for every day wear.

When putting together an outfit pairing a charcoal suit with a white shirt and black tie will always win with A+ style points. A charcoal suit with a black shirt and white tie is also a great look, especially with black shoes.

For colder weather, you can also throw on a vest or a sweater, with a charcoal suit under a brown or black jacket.

If you are looking for a charcoal suit on a budget, try shopping at a thrift store for a nice wool suit and have it tailored to fit you properly.

V-Neck Sweater

The V-neck sweater is the epitome of comfort and class, and it works with many different outfits. When picking the V-neck sweater, make sure you choose one that doesn’t point downwards. You want to avoid anything that is a too low V-neck. The sweater that is good for small chests is anything that has a V-neck, but that has a swoop of fabric that covers your chest and chest hair.

Grey V-Neck T-Shirt

Think of any movie where an athlete or a rugged and badass man is on screen. What color is his shirt? No, not white. That’s reserved for your old-man grandpa that is. First, let us understand the difference between fashion and style. A fashion trend is something that is popular for a short amount of time and then becomes out of style. A style is something that is a constant, almost like a uniform.

A v-neck t-shirt is the quintessential “form-fitting without exposing your chest” t-shirt for every man. Whether you are a bodybuilder or a regular Joe, every man can look good in a v-neck. The v-neck shows off the chest a bit and it allows the shoulders to keep their natural masculine width.

Dark Jeans

Dark jeans are essential for every man’s closet. They are the backbone of your everyday wardrobe. They can be paired with just about any shirt or dress shirt—and even a sport coat. Dark jeans go with everything and they are a great transitional piece for the fall and winter. It’s also one of those pieces of clothing that you can dress up or down depending on the occasion. You can find solid colored jeans in anything from black to stone to midnight. Colored jeans are completely acceptable for the office as long as they are not bright and they are not ripped. With a pair of dark denim jeans, you can add a pop of color to a gray dress shirt.

Shoes

In all occasions a man should be wearing neat, well-polished shoes. This is an important item to pay some special attention on. Your shoes should be one to two sizes bigger than your actual feet size. This is to prevent from foot cramps and blisters.

Wear well fitting and high quality leather shoes. Leather shoes are more breathable than synthetic ones, and they will age better with time.

A good pair of shoes will last for many years, so you should pay attention to the quality when buying them.

It’s good to wear some comfortable soft woolen socks that still keep your feet warm, but will not make your feet sweat too much. Socks should always match the color of the pants you are wearing. Usually dark colored shoes require dark colored socks. Bright socks should be worn with brighter colored shoes.

Shirts

A lot of men miss out on wearing some really great shirts because they don’t know where to look. In general, there are three places that men’s shirts are available from: department stores, online stores, and thrift stores.

Thrift stores are your best bet for finding shirts, because they have a huge inventory of different brands and styles. You can look for designer shirts in good condition. You can also find a lot of custom made shirts and even some vintage shirts if you’re lucky.

When you go shopping, you should pay attention to the quality of material that the shirt is made out of. Make sure it can hold its shape, has no rips or holes, and isn’t faded or stained.

You should also pay attention to the fit of the shirt. If you buy a shirt too big or too small, you won’t look good. A shirt that fits well is flattering to your body type. It is not too tight or too loose.

Don’t forget the details like the collar, the sleeves, and the buttons. A collar should fit close to your throat, it shouldn’t hang loose. If the collar is too tight, it will cut off your circulation and you may feel uncomfortable.

Polos

(For Men)

A polo shirt is a great fitting shirt choice for most guys. They fit comfortably, and can come in solid colors as well as stripes. In addition, they are thin and breathe well, making them great year round choices.

Polos can be worn both to work and after hours, and you can find them in a range of price points. In addition, you can pick them up from most department stores, and even the big-box variety stores. As such, you will be able to find polos in your favorite colors and patterns, all without breaking the bank.

Navy Blazer

Navy is the top choice when it comes to color. Since navy blue is the standard for formal dressing, you will find yourself being as successful as the men who wear it in the workforce. The blazer can be worn with only the pants or as a suit as well.

It’s very versatile which makes it a staple despite the popularity of gray suit colors. The blazer is the best choice because the collar can be worn either open or in your collar and tie combination. In the context of wearing a navy blazer, a tie is not a part of your ensemble. You can wear other bands, large or small, made of leather, silk, or a variety of fabrics.

One of the more popular combinations, which can be worn year-round, is the navy blazer with a white shirt and light colored denim. If you are the love of autumn, then you have chosen the correct color palette. If you’re not big on having large pieces of clothing, you can try scarves, cardigans, or vests.

Remember that you are dressing for yourself, so the right fit is what you are going for. If you see trends on TV, don’t follow them. Just do what feels right and be patient with yourself.

Eliminate The Same-Old

The key to looking good in clothes that aren’t necessarily made for you is to fit your personality and your style into them. Don’t feel like you have to dress like a square if you’re not a square. For example, if you’re into backpacking and hiking, you might want to wear hiking boots to work. Joggers can wear nice trousers and collared shirts with a thick sweater.

If you’re a professional racer, wear racecar driving shoes, and shave your legs if you’re a swimmer. Look how comfortable a race car driver is sitting in the seat of that car. He’s got jean-like stuff going on because jean-like clothing is comfortable.

That doesn’t mean you should wear a kimono to work. Just look for ways that you can wear your personality on your sleeve.

Don’t Go Fashion Crazy

You might think fashion is the main expense when getting dressed, but neglecting the other components of style means you’re wasting your money.

We’re talking about very basic components of style that are just as important to your overall look and are very affordable.

Basic style components include:

  • Good Shoes
  • Socks
  • Nice Accessories
  • Good pants
  • A good belt

The first thing you want to do is focus on getting all the other pieces right. Things like accessories, pants, belts, and so on should take precedence.

When you’re working on the basics, you know you’re getting good value and it frees up the budget to go crazy with fun pieces of style that will make you stand out and look distinct in subtle ways.

You’ll be amazed at how much a nice pair of pants, a good belt, and a nice pair of shoes can do for your overall style.

This goes for shoes for both dress shoes, which are the foundation of what you wear, and casual shoes.

Fabric Is Your Friend

Choosing fabric over denim is going to add a softer, more tailored fit to your outfit. Many dress shirts are made from cotton, linen, non-stretch silk, or a blend of fabrics. There are pros and cons to each material, however, and a lot of them are on a sliding scale.

Unlike denim, most dress shirt fabrics allow for full mobility, which is extremely important when it comes to wearing them in your day-to-day life. Linen and cotton shirts are definitely the most comfortable, although a few shirts made of silk or synthetic blends are also comfortable.

Some people enjoy the rugged look and feel of many denim options, but when fabric is your friend, you’re going to have a more versatile piece that you can wear in a variety of situations and styles for a long time to come.

100% Construction

Knit construction apparel is a must. It resists wind, moisture, and odors better, and breathes. The stitching is strong enough to hold seams together when machine sewn, and knitted construction will not snag and unravel like woven fabrics tend to do.

Fabrics — Avoid "fancy" fabrics of all kinds in the construction of men's work clothing. Fancy fabrics are things like silk, satin, velvet, corduroy, and the like. These fabrics may seem nice, but the reality is that they don't stand up to hard work the way plain, heavy-duty cotton and wool do.

In a pinch, you can use these fancy fabrics, but only with garments that are made of lighter weight non-construction materials. The lighter weight of these fabrics will make them less suitable for hard work, and more suitable for hanging out in town.

Stitching — Always use at least four- to five-consecutive-thread stitching. Two-thread stitching simply doesn't hold up when subjected to hard use.

Color — Avoid colors and shades that advertise where your clothes came from. That means avoid color combinations with your company name, the city name, or anything similar. Instead, go for earth tone colors, and even those in neutral shades.

Right Weight

You can have a great physique and still not look like a man. Your skin is your canvas. If it’s not strong and thick enough, it will sagg, wrinkle, and wrinkle. Not to sound like a broken record, strength is the key to everything in life, even in aesthetics.

So the best manly advice I can give you is to get the weight off your fucking bones.

Check the Weave

If the suit is heavy or the cut is boxy, chances are the suit has a blend of polyester. If the suit seems a little lighter and the material feels a little softer, it’s probably a wool suit. Some high end designers may even trick you by merging the two fibers to make it look like a wool suit, but in reality it may have a little bit of polyester. Do your due diligence while checking out the material of the suit. Use your fingers to feel the material and see if there’s any scritchiness on your fingers that would suggest synthetic material.

The fabric of a suit is very important. It’s the main way you can feel and see the quality of workmanship that goes into a suit. The material that makes up the suit should be aligned properly, so the suit is comfortable.

Overall, there is no right or wrong answer to a fiber blend, as long as it looks and feels right to you. In terms of comfort, remember the words of the great Italian designer Giorgio Armani, “A well-fitted suit should not just look like you borrowed it from your father. It should fit you like a glove.” So a little scritchiness and a little tugging should not be a big concern for you.

Take Care Of Your Clothes

Taking care of your clothes is one of the most important things that you can do to keep your appearance up to date. It’s almost a necessity to keep your clothing in great condition, but it’s also important to make sure that you don’t ruin it overly quickly as well.

Get a press and put your clothes on a hanger to store them.

This helps prevent creases and helps keep them neat and tidy. You should also take care to fold your clothes so they don’t get stretched out or creased.

This will allow them to last much longer. The more you can take care of your clothes, the longer they will last, and the better they will look.

Don’t try to do any ironing or cleaning in the washing machine. You should use a functional iron and you should hand-wash the clothes.

This will keep them in good condition and keep them looking great.

Grooming

Men should attend to hygiene and maintain a clean body, mind and home.

Keep your fingernails clean and cut short. Never extend past your fingertips.

Cut and trim your finger and toenails straight across. Nail scissors should be kept at the bathroom next to the sink, not in the kitchen.

Trim your hair to within an inch of your scalp.

Wipe your face and neck with a clean wash cloth every morning. Use water and a light soap. Rinse off. Shave your face on a regular basis.

Use a gentle shampoo that is free of harsh chemicals.

Use a bar of soap to wash your body. Use a clean wash cloth. This is best done in the shower.

Dry off with clean towel.

Brush your teeth at least twice a day with a soft toothbrush. Wash the brush after each use.

Use a soft floss to clean between your teeth.

Inhale. A man’s breath should smell fresh and clean.

Rinse your mouth with water and a toothpaste after eating. Use a tongue scraper to remove food on the tongue and between the teeth.

Sleep on clean sheets. Change your sheets every 2-3 weeks. Hang them out to dry or place them in the dryer for a few minutes before putting them back on the bed.