Article: The classic way to wear a trucker hat is facing forward and fitted to the head. This is an easy, comfortable position that can give off an intelligent, laid-back vibe when worn with the right outfit. Try wearing black fitted pants, a white v-neck, and a jean jacket with your forward-facing trucker hat to achieve this look. If you wear your hat straight backwards, it might look a little retro-gone-wrong. Avoid this fashion faux-pas and go for a much cooler look by placing the back of the hat just above your hairline and allowing the bill to point downward behind you. If you like to be more daring with your fashion choices, put your hat on so that it's facing forward with the bill coming out from your upper forehead horizontally. Then, lift the bill up so that it moves from your forehead to just past your hairline and is about halfway between horizontal and vertical. This makes for a fashionable European-inspired look. While wearing billed hats sideways was somewhat acceptable during the 1990's, it's no longer a trend. Go with a forward-facing or rear-facing position instead if you want to be stylish.
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Wear it naturally facing forward for a smart, casual look. Wear it backwards and pointed down to give off a cool vibe. Pull the bill up to get a bold, trendy look. Avoid wearing your hat sideways.