16. Casual Preppy Street Ivy
What This Idea Means
Casual Preppy Street Ivy takes traditional East Coast collegiate Ivy League staples—varsity jackets, cricket sweaters, polo shirts—and updates them with oversized streetwear proportions, skate sneakers, and raw streetwear attitude.
How to Make It
- Base Layer: A structured Oxford cloth button-down (OCBD) worn untucked, or a heavy-gauge rugby shirt with a white contrast collar.
- Outer Layer: A heavyweight wool varsity jacket with leather sleeves and chenille chest patches, or a deep V-neck cable knit cricket sweater.
- Bottoms: Relaxed pleated beige chinos with a slight ankle crop, or loose vintage denim shorts.
- Footwear & Accessories: Two-tone penny loafers worn with crisp white crew socks, or low-top retro basketball sneakers, styled with a corduroy baseball cap and a canvas tote.
Styling Tips & Variations
- Layer the collar of an Oxford shirt over the ribbing of a crewneck sweatshirt for a classic Ivy aesthetic.
- Swap traditional loafers for chunky lug-sole loafers to give the outfit an edgier street stance.
- Choose varsity jackets with unexpected modern color combinations, such as forest green and mustard or dusty lavender and cream.