How to Dress for Success

How to Dress for Success

Being well-dressed is not a pursuit of vanity; it’s a way of life. The way you dress is the outward expression of your inner self. It can convey a whole host of things about you—whether you are self-confident or insecure, whether you are cultured or not, and so on. It can make you approachable or unapproachable, impressive or diminutive. It is a method of communication that doesn’t involve words. Unlike other attributes which people consider to fall under the category of “well-educated,” such as being eloquent, well-read, mindful and kind, clever and funny, having flawless etiquette, and others, dressing well doesn’t require years of training and diligence. There’s a small “learning curve,” but, short of that, dressing well is one of the easiest ways to make a good impression.

Have you ever wanted to simply walk into a room and have all eyes draw towards you? To simply stand in a corner and have ‘presence,’ without saying anything at all. Think exuding a James Bond-type aura. Sounds great, right? This all can be achieved.

Contrary to popular belief, dressing well doesn’t have to cost ridiculous amounts of money. If you can, though, setting aside a small extra budget for clothing/grooming items is not a bad idea. Once you build up the basics of a good wardrobe, however, you’ll won’t ever need to buy lots of clothes or spent too much money doing so.

What kind of style do you want to personify?


Think about your lifestyle and what style icons/celebrities you admire. How do they dress? If your lifestyle is more casual, and you prefer casual, comfortable, clothes, than your wardrobe should consist of laid-back pieces like jeans, t-shirts, and sneakers. If you have an office job with a dress code, you’ll probably want to invest in a more dressed-up style, because your pieces will be versatile enough to wear both inside the office and out. And, remember, dressed up doesn’t have to be conservative! Give thought to what kind of shoes you wear, too, as this will determine what kind of trousers and shirts you should purchase. Certain types of heels, for example, only pair with certain cuts of pants.

Build up the basics.

What are the basics? Most are simple, single-color pieces. For almost any style, similar basics apply. Here are some tips.


For any gender, a good pair of dark-washed denim jeans is indispensable. You can dress them up or down, and a good-quality pair will last years. Similarly, a pair of black jeans is a great investment and go with anything.

Style7For those who work in an office, we suggest a pair of black, gray, and navy trousers. Women can sub the trousers for a skirt if they wish. For men’s suits, if you’re just starting out, you really just need two: gray and navy. The suits should be slim cut, two button, no pleats. Don’t buy your suits too big! Many men make the mistake of wearing baggy suit pants with jackets that are far too wide at the shoulders, too long at the sleeves, and too ‘fat’ for their bodies. Similarly, button down shirts should be snug when tucked in—no rolls or Consult GQ for a suit buying guide and more tips.


Style6Basic tees are essential for both men and women. One in black, gray, and white, and you’re good to go. For button downs, at least one in white and one in blue. A sweater in gray or black will also be great for layering and goes with lots of outfits.


This really depends on personal preference. Pick your shoes based on what you can wear all-day comfortably. For shoes, it is worth pulling out the big bucks. Not crazy amounts, of course, but investing in a shoe that’s over $30 will pay off, as it will look much better and last much longer than a lesser-quality shoe will. Moreover, cheap shoes look, well, cheap. Black shoes are the most versatile color when it comes to any type of dress shoe. Men should look for dress shoes with a long, rounded toe. Your dress shoe should strike a balance between roundness and pointiness. Square, circle, or other toed shoes look cheap and clunky. Your dress shoe should be long, narrow, and slimming. Any other type of shoe is reminiscent of a work shoe, like those used in the restaurant industry, which are designed not to be pretty, but to be practical and non-slip.

Style8When it comes to heels, pick what’s comfortable first. Wedge heels and chunky heels can look great while providing comfy, all-day support. Stilettos are always sexy, if you can pull them off. While high heels can add a total bombshell and power factor, a woman hobbling in heels doesn’t read of confidence.

For sneakers, a sleek white is the way to go. Don’t go too chunky on the sneakers, and make sure they aren’t athletic (running) shoes. Keep athletic shoes in the gym. After you have black shoes, invest in a pair of cognac/brown shoes. Make sure the brown leans more towards the orange/cognac end of the spectrum—this unique cognac color matches far more than regular brown does.



For women, a black purse is first up. Then cognac or grey. Men: black belt, brown belt, same for women. This is essential: make sure your belt and bag match your shoes!  A leather brown or black briefcase/bag will go with most outfits. A black or beige scarf is a great starter scarf.


Unless you have a very diverse and extensive wardrobe, mixing metals is difficult. When first starting to built your jewelry/accessories collection, it’s easier to start with one type of metal. So, go silver or gold and stick with it for a while.

A simple classy watch is a must for the dapper man and elegant woman. Avoid plastic or rubber straps–those can look tacky. Instead, a watch with a nice leather or metal band is perfect. Keep it simple: don’t get watches that are too big, have too many faces, or excessive detailing such as diamonds or crystals.

A ring or two can add a nice touch and a hint of character. Don’t go for anything too gaudy, pick a simple band with a nice gem, and make one or two of such rings your trademark.


Inspiration can be found in magazines, on the street, and on the net. Great websites to look at are, GQ, Ralph Lauren, Mod Cloth, Express, Macy’s, and The SartorialistGirl with Curves.

Where to Buy

aFor all clothes, you will likely find the best deals online. Tape a tape measure to yourself to find all your proportions. Clothing sites will always list the proportions and measurements of their sizes. This will help you choose a size that best fits you. Also, if you’re on a website with a brick and mortar store, go to the store to try on a few basic items, so you can determine what your size is in that brand. This will make shopping online much easier. Browse Google for coupon codes and sales which will make your purchases cheaper.

Find your favorite stores, and don’t be afraid to search online. Buying secondhand is a great way to be able to afford designer clothing. Try sites like Amazon, eBay, and Of course, you can’t get away with paying nothing to look good, just like with any endeavor. But trust us: the investment is worth it. Not only will you look better, you will feel better. And remember this quote: “being well dressed is a beautiful form of politeness.”


Guest Contributor

Guest Contributors occasionally check-in to the Urbyn Loft to share insights in Entertainment, Sports, Gaming, Business, and Culture.

Latest posts by Guest Contributor (see all)