Stuck in the '90s? How to Upgrade Your Look

Some items never go out of style — some do, including a few of those pieces you still have hanging in your closet and packed away in your dresser. Replace what you see on the left with these modern classics on the right.

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Out: Oversize Bomber JacketA too-big bomber in distressed leather screams dated. Leave the relic to Goose and Maverick.

In: A Fitted Leather JacketLook for a minimal design and lightweight leather, as with this Schott jacket. [$750; schottnyc.com]

RELATED: The Leather Report: 4 Jackets to Wear Right Now

Out: The Free T-shirtTypically made of rough, cheap cotton and two sizes too big, it's no way to commemorate the 5K you ran in 2006.

In: A Well-Made TeeNothing gets as much wear. Invest in quality material and a size that doesn't billow or hug. Our pick: Splendid Cotton Crew Tee. [$58; splendid.com]

Out: Shapeless, Light-wash JeansSuburban moms have stopped wearing these. So should you.

RELATED: 10 Perfect Fall Boots

In: Dark-Wash DenimThe antidote to acid-washed. [$70; levis.com]

Out: Chunky SneakersThe boxy shape makes you look more square, and no foot needs a pound of cushioning.

In: Low-Profile Tennis ShoesYou don't want to look like you're wearing your kid's Jordans. Try these Cole Haans. [$150; colehaan.com]