Which boots should I start with?

Timberland Redwood Edge Essential Chukka Boot Beige Nubuck is the most adaptable option. Beige and Nubuck give it a straightforward look, while the Chukka shape is easier to style than the Black Waterproof or Chestnut alternatives.

Which Chukka boots suit a college campus day?

Men's Coach Chukka Boot in Signature Suede Tobacco Maple suits a college campus day when you want a warmer colour and Suede finish. Redwood Edge Beige Nubuck offers a quieter alternative.

How do the materials differ across these boots?

Suede appears on Rowan Way and Coach Chukka Boot, Nubuck appears on Nellie, Redwood Edge and Timberland Chukka Boot, and Waterproof appears on Nellie. Ugg Burleigh and Coach Coconut offer other choices.