What I Have Learned About How To Dress Yourself

Always Dress Up: How you dress not only affects how others see you, it affects your mindset as well. When I dress up for work, it puts me in the mindset of a professional ready to work, which helps me project that as the first impression others get.

The psychological effect runs deep; weekends where I don’t get out of my pajamas are days where I rarely leave the house. On the other hand, if I start the day dressed as if I were going out, it makes it much easier should I decide to do so.


Keep Your Shoes Shined: Scuffed shoes immediately dress you down. Conversely, a good pair of well-kept dress shoes almost always dress up an outfit.

Whether consciously or unconsciously it keeps you in the mindset of caring about how you look, which helps project that as part of your first impression. Dressing in business casual attire is something anyone can easily do; shining your shoes requires effort.

When I see someone wearing business casual, or even a suit, with scuffed shoes, it gives a negative first impression; however someone wearing jeans, a dress shirt and well-kept dress shoes gives a positive first impression, over and above the suit-and-scuffed-shoes.


Pick a Signature Style: Standing out a little never hurts. In this age of networking, anything that helps people remember you is a benefit; you need to stand out in peoples’ memory so you come to their mind more easily when they are looking for someone to fill a purpose.

It could be jazzy ties, or snazzy socks. It could be stylish hats, or unique belt buckles. Pick something that resonates with you and then run with it. I don’t like ties, and don’t care so much about shoes and socks, so belt buckles are my trademark.

Don’t get me wrong, it is far better to be remembered for your work and reputation, but this is easy to do, doesn’t hurt, and often makes a noticeable difference.


Have a Good Tailor: “Everyone looks good in a tuxedo.” Even rented tuxedos are tailored to fit properly when you get them. You will always look better when your clothes fit you properly.

Any time I get a new pair of dress pants or jeans, I take them to my tailor – I tried a few and stuck with the one I liked the best – not just to have the length corrected, but to adjust the waist, seat, and leg-taper to fit me properly. It inevitably looks like I spent a lot more than I actually did.

The better look and increased comfort from the tailored fit positively affects your mindset, which affects the first impression you project. Being confident about how you look is definitely a visible trait.


Never Neglect Comfort: This one is pretty simple: no matter how well dressed you are, if you are uncomfortable that will come across in your interactions with other people. This goes for visual comfort as well as physical.

You might fidget a lot, or be more irritable, or distracted, but regardless it has a negative impact on your mindset which detracts from the first impression you project.

Physical discomfort can sometimes be remedied by a trip to your tailor, or something as simple as wearing an undershirt. But always make sure you feel comfortable in what you are wearing. Unless it is Halloween.


The Whole is Greater than the Sum of Its Parts: it is the combined effect of all of these that makes it solid. Picking one or two and ignoring the rest never works as well.