Should your clothes always fit? No way Jose'. There are times when the exaggeration of over sizing or under sizing is the perfect choice. Let me give you some current fashion examples. Oversize (also called chunky) turtleneck sweaters with very thick collars are very in right at this moment for the coming fall season and they look great.
The sweater itself is not oversize, it fits comfortably although a bit loosely, but the collars are very large and that is where the over sizing looks good. Big, bulky sweaters of this type are definitely a nice look. Oversized scarves that create the same type of look are in fashion for the same reason. In winter jackets, over sizing is important because the winter jacket must fit over your other clothes that might consist of a full suit or a shirt and heavy sweater depending on how cold it is outside.
It used to be that pants were worn as over-sized if you were part of the hip hop crowd but that trend is disappearing fast. One thing that is oversized and is fun to wear is a men's sleeper, which is basically a very large and long t-shirt that comes down to your knees and is worn to sleep in at night instead of pajamas. Men's watches are trending towards larger sizes also with chronographs that have every kind of dial to tell you the weather and even your altitude, many of them are quasi-military.
The big black men's shadow watches that are in fashion now and they are essentially all black color and oversized. Some of these are so black you cannot hardly even read the dial. Oversized wool knit ski hats are fun for the younger crowd. Stay away from those oversized ugly mukluk boots also called Uggs anywhere outside of the ski lodge, they don't really fit in anywhere else.
What about undersized? Half vests are interesting when they are made of leather or made out of something unusual such as chain mail. Tight pants are useful to advertise the merchandise. If you got it, flaunt it. There are some nice tight pants that only come down to halfway below the knee which look great for going to the beach or for a walk with the dog.
Suits can be tight-fitting and jackets can be undersized, which is all the more dramatic for the "reveal" when you remove your oversized outer winter coat as you come out of the cold to enter a fine restaurant. If you have rock hard abs you can wear a tight fitting t-shirt, but for any other body style especially when you are a bit overweight this is not a good choice. In other words, if you are oversized, then your wardrobe should be empty of any undersized clothes.
If you are skinny as a rail, then under sizing is fun, when you can get away with it. Glasses and regular hats need to fit you properly and the trend is to be more sedate in your sunglasses choice so avoid that Elton John look. Mix and match sizing where appropriate and you will have some real fun.
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