10 Tips On How to Dress Like a Man

While running shoes are great for a vigorous workout, there is really no need for these shoes to be worn beyond that. For casual situations, moccasins or canvas shoes (think Vans or Converse) work well. A pair of leather shoes, especially in a caramel-y brown (so they can be paired with black, navy, gray and a darker brown), are extremely versatile. Not only do they work in formal settings but they can even dress up a pair of dark-wash jeans. You don’t need 20 different pairs of shoes to dress like a man but you do need more than running shoes. A small handful, when bought in a higher quality, will take you far.

How to dress like a man
How to dress like a man

Find a suit that fits properly.
Many men thatI know own suits that are too big for them and they don’t even realize it. Their suits are too broad in the shoulders, leaving their heads looking small and looking as though they’re a child trying to fit into their dad’s suit. I think that one of the best investments a man can make is to get a custom-tailored suit. On the front end it will cost a bit more, but when a suit fits properly you can wear it for almost any occasion. The top and bottom can be worn separately for different looks and situations for even more versatility. A suit that fits well will never let you down.

Trade trendy jeans for something a bit more classic.
Skinny jeans in an array of colors have been the thing to buy the past couple of years, and while a fling in this direction can be fun, it’s better to invest in something a bit more timeless. Moving from skinny jeans to either a slim-straight or relaxed fit will serve you better in the long run. Most people don’t have the lanky 19-year-old body that can pull off the skinny jean look anyway. Buying a straight cut in a dark wash makes jeans wearable from a baseball game to date night, as dark jeans can be dressed up or down. Versatility is a beautiful thing, and so is a pair of jeans that isn’t too tight or too baggy.

Move from sweatshirt to sweater.
Most sweatshirts will pretty quickly pigeon-hole you in the college or athletic demographic. A sweater can not only step in to fill the role of a sweatshirt, adding warmth and layers, but also works far beyond that slim area of life where a sweatshirt is appropriate attire. Sweaters come in all styles, from crew and v-neck to pop-over and shawl-collar and even cardigans. All of these styles are conducive to layering and require very little effort to make an outfit look complete. If it’s the coziness of a sweatshirt that you like, just look for a sweater in a chunky knit. However, many sweaters come in a very light knit as well, allowing for layering when a sweatshirt would be too heavy. And, on top of warmth, layering and coziness, sweaters can easily transition from one situation to the next with ease. A sweater can be worn as easily at a wedding or out for dinner as it can on a camping trip around the campfire.

Athletic socks are for athletic events.
Buy darker dress socks for everyday wear. Not only will they blend in better with most outfits, but they will fit more comfortably into most shoes. Wearing this style of sock also lets you add a bit of visual interest if you opt for a patterned sock, such as argyle, but if properly worn will not distract from the rest of your outfit.

A workout T-shirt should not be your everyday T-shirt.
Differentiate between athletic shirts and those you wear out on a casual day. An everyday T-shirt should be of a higher quality than a T-shirt you get for free after running a 10K, and can be more versatile in color and neckline. However, opting for solid colors in general, as opposed to graphic tees, will serve you better in the long run, as solids can be paired with more. Be cautious when wearing a T-shirt, however, as they aren’t appropriate for every situation. Know when to dress like a man by dressing it up with a button-down instead.

Incorporate different patterns and textures.
Gingham, stripes or plaid are great ways to mix up some of your basics and add a bit of color. Patterned button-down shirts can easily be layered with sweaters or blazers for a lot more depth. A classy pattern makes it look like you put a lot more thought into your outfit than you probably did. Playing with textures such as tweed or seersucker, depending on the season, adds tactile as well as visual interest. These textures can be applied to tops or bottoms, but when wearing bold patterns and textures make sure you pair them with something a bit more neutral.

Hats are great for fighting against the elements…
…whether it’s the sun or the winter wind. Most men gravitate to either a baseball cap or a beanie, but there are so many other styles that can add a little more class to your look. A straw fedora can be great for a sunny day, and gives off a beach-y, casual vibe. A wool bowler or fedora can be great in the rain, keeping you warm and protecting your hair while offering a classic Cary Grant-esque look. Men can get away without accessorizing too much, but adding a hat to top of your look can not only be practical but also give you a timeless look, adding an interesting element to an otherwise basic outfit.

Leather is the best choice when looking for a wallet.
If your current wallet involves any sort of velcro or superhero decal, it’s probably time to move on. It’s really hard to go wrong with a simple tri-fold leather wallet.

Be confident.
It’s okay to experiment a bit when learning to dress like a man in a classier manner, but whatever you wear, walk around with confidence. You are a man, and you’re beginning to dress like one. Don’t be afraid to take some chances, but remember that a gentleman’s look is timeless. Spend time shopping for the proper fit and move away from trends and toward something that will last. Dress like a man.


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