Chukkas are a great first shoe.
They sit between casual and formal, and can be worn during fall, winter, and spring.
I wear chukkas most with jeans, corduroys, chinos, and odd trousers. They’re my go-to shoes.
Wearing chukkas with worsted wool tailoring can look odd.
Why? The casual suede clashes with the rather formal worsted fabric. Suede also looks too warm next to the glossy fabric.
Chukkas tend to have fewer eyelets (between 2-3), so they conveniently slip on and off.
A dark brown chukka would be the most useful color, followed by mid-brown and sand.
Overall, chukkas are versatile, tasteful, and not fussy at all.
*Photo: Funny, I spotted this familiar chukka model at Purdey, who partnered with Crockett & Jones to make this shoe. I have the same one from Crockett & Jones, but in chestnut.