Dressing well does not mean wearing a custom 3- piece suit everywhere you go. It just means looking your best in whatever environment you are in.
Being a well-dressed man may mean having a well-fitted suit as opposed to something cheap and off the rack, or it might mean adding a blazer or tie when you could get away with just a dress shirt in a less formal work environment. It can be as easy as putting on a sweater or vest when you are out with friends and wearing nice loafers instead of tennis shoes.
You can look well-dressed in anything if you always make sure the men suits you wear fit properly. You can’t look good squeezed into something you bought five years and 20 pounds ago, even if it was a really nice piece of clothing. Just make sure you’ve got a good, consistent fit all around: long sleeve shirts should extend just to the wrist and hang reasonably close to the body. Pants should fit close to the body and “break” by resting lightly on the tops of your shoes. Jackets need to give your arms freedom of movement without pinching and to cover your bottom when you stand.
One of my favorite outfits to wear when meeting with a client, speaking to groups about my business, or meeting up with friends is a dress shirt, a tie and a buttoned vest paired with a nice pair of jeans. It works in business environments but also works in a more casual setting. For an “off-the-clock” look later in the day I even loosen the tie a bit.
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