Step 2: Assessment

Self-assessment in any capacity is difficult. In my experience, it starts in times of prolonged isolation. Downtime at work, car drives home without music, and even forgetting to bring your phone to the toilet, can all trigger some level of self-reflection.

More often than not, these moments have nothing to do with style… directly. I will go out on a limb and say that many of your problems begin in the bedroom—more specifically, your closet. If you’re in the dating world and not attracting the right type of person, it may somewhat be attributed to your looks or weight, though Beyonce did marry Jay-Z. Money aside, you have an opportunity to show that you’re a cut above the rest with your style.

Another example, feeling that you’re not well-respected in the workplace. It may be your confidence, or just being the “new guy” at work, but if my military experience has taught me anything, it’s that a well-polished pair of shoes and pressed uniform can (and will) let you get away with murder.

Getting back to assessing your wardrobe, go into your closet, take everything out, and look at what you have.

• What do you wear most often? Put that away.

  • The best time to do this is right before laundry day because obviously, you wear all of that clothing at least semi-regularly.

• Anything with tags, get ready to resell or donate.

• Anything leftover, get rid of it.

  • This will be more than you feel comfortable getting rid of. Get over it. The clutter was affecting the rest of your life in ways that I’m not qualified to discuss. Trust the process.

As men, this probably wasn’t that hard. Most people have a few pairs of jeans, some joggers, maybe shorts, and 10-20 t-shirts of varying styles. Shoes are always a toss-up, some men have one pair of running shoes and maybe a pair of “going-out” shoes. This is a much easier fix. Plain sneakers, leather boots. I have another series beginning this Wednesday “Application” further discussing this very simple style upgrade.

Now that you have your core wardrobe, two-three pairs of jeans, your favorite shirts, some shoes, and two to three jackets should get you through a week or two until you watch these videos and make some sound decisions.

Men’s Fashioner “Year-Round Essentials” playlist:

https://www.youtube.com/playlist?list=PLPCBY2Zswqehqud3uIid8ba03G8aek7FS

• Note: The playlist is ALL inclusive, so find the videos that apply to your climate, time of the year, and of course—style.

HeSpokeStyle “How to Build an Essential Menswear Wardrobe”:

https://www.youtube.com/playlist?list=PL3v2lRj6jZMfVJccRxM8eChpLEsaHD0hw

• Note: This is a much more “dressy” option, but it’s where I started!

Sartorial Talks — “How to Build a Wardrobe pt. 1, 2, and 3”

• Note: You will buy a suit after this master-course in style.

Of course, there are other options. Some of which I listed in my previous article “Step 1: Inspiration.”

Finally, there is the last issue at hand for a thorough assessment.

Finances.

Luckily, the next step in this series will address exactly that. Look out for a list of stores to buy from, ones to stay away from, the best online interactions, and all of these in a variety of price ranges.

“Dressing Up” has nothing to do with finances… though it does help to have some nice shoes.