Matter?
You could argue that nice clothes are nice clothes, and that you should be able to wear the same ones on and off the clock.
And it turns out you can, if you want to! There are men who don't bother differentiating between their work clothes and their social clothes.
But small changes can help to send a useful signal. A man who looks good in his work clothes still looks like a man who just came from the office.
A man whose clothes clearly could not have been worn at the office, on the other hand, is making a deliberate statement: "I don't look this way by accident."
It tells people that you're not just someone who buys good clothes, you're also someone who thinks about how to wear them well. And that's a subtle distinction -- but a flattering one. Even people who don't think it through consciously are still more likely to identify you as a "sharp-dressed man" when there's no question of it being accidental.
It bears mentioning that you shouldn't even consider going the opposite route -- that is to say, buying fancy-looking evening clothes and then wearing them into work. That makes you look like you came straight from the Walk of Shame, and it does not say good things about your character.
How to Transition from Work Wear to Social Wear
Switching from an on-the-job look to an off-the-job look is one of those "your mileage may vary" situations. The best way to do it depends on what you wear to your job.
But in general, the goal is to have at least one clothing element that is not work-appropriate, at least in the mind of the average viewer.
Here are some quick examples of transitions that can make a clear distinction:
Men who wear ties to work can shed the tie, open the collar, and perhaps even undo the top button on the shirtfront. This is almost mandatory -- unless you're going somewhere very formal, no neckties after 5:00 PM or so.
Men who don't wear ties can throw on a shirt or a jacket that's too brightly-colored or vividly-patterned for conventional offices.
If there's no chance for a change (going straight from work to drinks at a bar, say), rolling up the shirtsleeves is always a good way to signify "off-duty."
Upping the level of contrast in an outfit makes it less formal. That's why a lot of "social" shirts have multicolored stripes -- it lets one garment bring the formality level of the whole outfit down.
Anything that's a little on the flamboyant side -- colored leather shoes, say, or brightly-colored pants -- is definitely off-duty wear, and works well in social settings.
Long story short: give it some pop. Put some flair in your outfit. Don't go so over the top you look like a clown, but don't be afraid to catch the eye a little. That's what makes it clear to everyone that you're not just some shmoe on his way home from the office.
Dressing Up at Night
All that works great if you want to dress down -- to relax, unwind, and let people know that you're taking it easy.
But what do you do when you need to go someplace dressy at night?
A couple easy strategies:
Wear a jacket. A suit is fine; so are blazers and dressier sports jackets. Avoid anything too unstructured, and make sure the fit is reasonably close -- you want to look at ease, but not slumped.
Skip the necktie. Unless you're going somewhere ties are required (such as some "white linen" restaurants), an open collar beneath a suit or jacket tells people that you're off-duty.
Wear dark colors. This applies to suits, jackets, and trousers, but it can apply to the shirt as well. Deep, rich colors like burgundy and forest green give an air of richness but still couldn't be worn to work, making them ideal for evening social outfits.
Play with contrasting formalities. If you need to look nice, but not stiff, pair something like a dressy blazer with dark, fitted jeans or a pair of Nantucket red pants. Or do the same thing with a nice pair of charcoal gray slacks and a casual, tweedy sports jacket on top. It's a way of effectively "dressing up
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