This is really weird. Just a couple of months ago, I wrote a newspaper column going on and on about how liberated I was because I didn’t own a suit. And now here I am with my own subscription to freakin’ GQ magazine. What a strange turn of events.
I have never really had a style to call my own. I was one of those in-betweeners never really dressing up but not quite dressing like the cross between a shadetree mechanic and a homeless person either.
For a long time, dressing up to me was wearing a sportscoat with my jeans and t-shirt. I have owned about six suits in my entire life, never more than two at a time.
My first suit after college was a gift from Aunt Jo. She took me over to a local men’s store, helped me pick out a nice navy blue number, one crisp white dress shirt and a maroon silk tie. I believe she even bought a pocket square to match the tie. It made quite an impression for my first sales job interview. Unfortunately, my lack of sales skills (or any skills at that point) did not leave a great impression and I did not get the job. Fortunately for me, I did not leave a great first impression because if I would have gotten that first sales job I would have sawed off my hand and tried to go on disability after about six months. That was 1987.
Since then, I have worn various degrees of dress up from suit and tie to sportscoat and tie to shirt and tie to something called “business casual,” which is usually oversized, comfortable chinos and a frumpy golf shirt (not POLO, but usually a golf shirt with a logo from whatever company gave it to me). This was my style, at least at work.
On weekends, I was even more laid back. T-shirts, jeans, or shorts were my go-to gear for going just about anywhere. For some strange reason, I used to tuck my t-shirt into my jeans or shorts for a more “formal” look. It turns out all that did was make me look like a “formal” twit.
Then about ten years ago, I jumped off the fashion train and jumped onto the much more comfortable fashion moped.
About two years ago, I gave up completely. I tossed out my last remaining suit, all my polo shirts (with or without company logos), my dress shoes (except one pair) and all of my slacks. All that was left in my closet were t-shirts, a few party frocks and three pairs of pre-washed, relaxed fit, boot-cut jeans. Oh, Jesus, was all of that comfortable. In facet, I bet Jesus himself would have worn the exact same outfits if he were around today. At least I used to think that.
Then the Summer of Change happened. It became the summer of 2014 and I needed a change. I needed an upgrade. I needed to do things differently.
Here are the four steps I followed to look more stylish and fashionable:
Step 1: Do a quick Google search for fashion blogs. I did and immediately found 2 million links to all kinds of ladies’ fashion blogs. I refined my search for “men’s fashion blogs” and came back with 4 million links to all kinds of men’s fashion blogs. Who knew that many men were into fashion? I did not.
It was eye-opening. I learned a ton.
For instance, I always thought that for a man to be fashionable, he had to be uncomfortable. That, I discovered, was not always the case. Many pairs of nice jeans, chinos, wool slacks, dress shirts, fitted polos and shoes of all kinds could be both fashionable and comfy. My God, I love the Summer of Change.
Step 2: Throw out your old shit. I went through my closet and through out all of my old shit. Well, almost all my old shit. I kept a few items to keep in the mix, but most of the old party frocks, boot-cut jeans and 27 pounds of old t-shirts went to Goodwill. My wife joined me in the fashion reboot and together we took about 10 garbage sacks full of clothes to be recycled. It was liberating and scary as hell all at the same time.
Step 3: Start shopping for a new look. I tried to buy just the essentials at first. Here’s my list of essentials:
1. Navy or grey suit.
2. One white dress shirt, one light blue dress shirt
3. Khaki and navy blue dress slacks.
4. Navy blue sports coat.
5. Brown dress shoes.
6. Black dress shoes.
7. Three or four dress polo shirts
8. Three or four nice white t-shirts (nothing in a bag).
9. A dressy henly-collared shirt
10. A nice grey sweatshirt.
11. A nice pair of white tennis shoes sans logo
I think that’s it. I haven’t purchased it all yet, but I’m slowly adding to it when it can. If you have these essentials, I discovered, you can mix and match to come up with a variety of outfits to wear to a variety of events, including events that might have called for a party frock in the past.
Step 4: Wear the new style. Dress up. Even if you feel slightly out of place, dress up. It’s amazing how much more respect and attention you get if you dress up.
Of course, that doesn’t mean wearing a navy blue suit with black cap toes to the beach, but it does mean make sure to wear the best in beach attire when you do hit the beach.
The main thing I learned was that things need to fit. For a man, that means trousers that are slimmer fitting around your leg and just long enough to touch your trousers with maybe a break about halfway up your shin. For shirts, they should hug your body, not too tight but definitely not sagging around your mid section like a produce bag full of broccoli.
A cheap suit can look expensive if it fits right. And an expensive suit can look cheap if it doesn’t fit right.
Find a tailor, get to know him and let him know the style you are going for.
Why should you dress up? Three reasons.
1. First impressions — It makes all the difference in the world. Pay attention to details — shoes shined, clothes with a perfect fit, pocket square, nice watch, tie bar, all the little things.
2. Respect. Dressing up makes you feel better and people around you treat you differently. My good friend Deion Sanders famously says, “If you look good, you feel good. If you feel good you play good. If you play good, they pay good.” And while I don’t want to play cornerback for the Cowboys, I would like to get paid well. (Call me Jerry Jones.).
3. Flexibility. Dressing up means you are flexible to do other things. If you wear a suit to work, you can take off the tie and throw on a nice polo or t-shirt with it to go out for drinks afterward. Your employee may want to send somebody to see a customer face-to-face. Who is she going to send, a guy with a well-tailored suit or the “business casual” guy with the baggy chinos and the red IBM polo he won at a trade show. Give me the suit guy any day.
Thank the good lord for the Summer of Change.