Originally Posted by Manton
Personally, I don't think cap toed shoes -- whether plain or brogued -- look particularly good with odd trousers and no jacket. I am probably in the minority on this, but to to me a cap toe is just too formal and demands a suit. Consider a pair of monk straps, which pair well with almost anything. Perhaps not the thing for a job interview or a funeral, but they can otherwise make the transition from shirt sleeves to suit coat very well.
I disagree, the Monk Strap is an advanced move and you might hurt yourself if you try this before you are ready. It's like trying a full-gainer when you've only yet just stopped holding your nose when you jump in the pool. Beware! I don't think black lace-ups crossover very well to jeans, ever. There are more dress occassions that will call for a somber lace-up, and a black cap toe is an excellent choice. You can opt out of any decorative perforation at the toe, and this shoe can go formal, too. The monk can't. Spend $400 or up on a great pair of lace-ups with a stitched welted sole, and keep them for when you are wearing a coat and tie. Get your self a pair of monk straps or slip-ons for business casual or going out in more casual clothes.