Bootcut Jeans, Three Ways

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Start with the bootcut jeans in your closet and pick the version that fits your day. Try the shoes and layers you already own before filling a gap.

1. With a striped tee

Try a close striped tee and small loafers. Let the hem graze the top of the shoe, leaving enough clearance to walk without catching the heel.

Compare black loafers 🛍 shop · amazon

2. With a hoodie and sneakers

Choose a hoodie that ends near the hip and a skate shoe with a broad toe. The wider shoe fills the flare and keeps the hem from collapsing inward.

Compare wide skate shoes 🛍 shop · amazon

3. With mesh and silver

Use a slim opaque base under a dark mesh layer and add one silver detail. Check the length with the shoes you’ll wear out; it can change with a taller sole.

Compare a dark mesh layer 🛍 shop · amazon

4. Check the fit before you go

Try on the jeans with both a flat and your tallest usual shoe. Choose the length that works with the pair you actually wear most.

5. Try this with what you own

If the flare feels too wide, try a subtle bootcut in a dark wash with a clean front.

Pick another piece from your closet or browse more Y2K outfit guides.

More ideas: A Mesh Top, Three Ways, A Graphic Tee, Three Ways, and more men’s outfits.