Rules will always apply to dressing to fit the occasion

Q

During most of my business life, I dressed rather formally, primarily in suits and blazers, and I thought of myself as a guy who knew a thing or two about how to look good. Nowadays, I am working in and out of the office (in person at the office and on Zoom from home). Sometimes I’m in a sport coat, but never in anything as dressed “up” as a suit. Still, I like to look good, without overdoing it. Do you have any thoughts on what is an appropriate formula to follow?

A

I am so glad to hear that just because your work environment has changed, you don’t think it means that “anything goes.” These days, the workplace is a very different place from what it was a while back. Since business casual has become the new norm, far too many men act as if dressing no longer requires any thought. Today, with so many fewer rules, it may be harder than ever to know what is appropriate to wear and what is not. Even so, never make the mistake of assuming that there are no rules and that dressing well no longer matters.

Of course, it still matters in all work environments. But, in addition, what also matters is how you feel about yourself. A man who likes to look good still pays attention to the clothes he chooses to wear and what they say about him to the world. If you think about what you want your clothes to project about you to others, you can discover what look works best for you.

So, what is the image you want others to connect with you? Is it class-act elegant traditionalist; or quietly preppy; perhaps fashion-forward style setter; or stand-out-fromthe-crowd not-your-average Joe; are you Mr. Super Casual; surely not the guy who doesn’t really care what he wears or how he looks? The clothes you select speak for you far more immediately than you might guess.

To ease decision fatigue, choose a base uniform you can wear on most work days. Then the items you add can reflect your personal style and should, of course, fit the occasion. To keep it simple, begin with a versatile pair of khakis and perhaps a pair of dark dress trousers, plus a dress shirt.

Pants: Unwrinkled, flatfront, well-cut styles are best. The darker the trousers the dressier the look. Cotton khakis and wool dress trousers are both good choices.

Shirts: Everything from a solid white, through stripes and small subtle patterns in long-sleeve, neatly ironed cotton dress shirts, range from a French cuff shirt to a button-down collar with the sleeves rolled up. Shirting material goes from more casual Oxford cloth to dressier fine broadcloth.

Belt: Any good-looking dark leather belt will pull it all together.

Shoes are where most people make their mistakes. Comfort does not have to mean clunky and ugly. Instead of the sneakers that everyone wears, buy a comfortable pair of handsome leather loafers. They’re always right.

For those days when more is better, you have a huge range of options to layer over this daily uniform: a navy blazer, tweed sport coat, cropped bomber jacket, quilted zip-front vest, cardigan sweater or V-neck sweater vest. A further upgrade might be the addition of a necktie.

In essence, what’s called for is attire that combines dressing appropriately with the comfort of a casual look (as long as the pieces are clean, in good repair and fit well). No matter what the day brings, you’ll be ready, looking good and feeling confident.