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.
Out: Oversize Bomber Jacket
A too-big bomber in distressed leather screams dated. Leave the relic to Goose and Maverick.
In: A Fitted Leather Jacket
Look for a minimal design and lightweight leather, as with this Schott jacket. [$750; schottnyc.com]
Out: The Free T-shirt
Typically 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 Tee
Nothing 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 Jeans
Suburban moms have stopped wearing these. So should you.
In: Dark-Wash Denim
The antidote to acid-washed. [$70; levis.com]
Out: Chunky Sneakers
The boxy shape makes you look more square, and no foot needs a pound of cushioning.
In: Low-Profile Tennis Shoes
You don't want to look like you're wearing your kid's Jordans. Try these Cole Haans. [$150; colehaan.com]