Leather dress boots that mean business

Questions and answers

Are these boots good for everyday office wear?

Yes, if your office allows smart-casual. The leather upper and wingtip detail look dressier than a work boot, and the rubber outsole handles wet sidewalks. They are ankle height, so they pair with trousers and dark jeans rather than suits.

How do Bar III boots fit?

Bar III men's footwear generally runs true to size, and these are listed in medium width only. The lace-up front lets you tighten the ankle, but there is no wide option. If you have broad feet, consider sizing up half a size.

Is $69.99 a good price for these boots?

It is the only new price listed, $69.99 at Macy's as of November 5, 2026, so there is nothing lower to compare against. For a genuine leather dress boot that is a low entry price. Watch for seasonal markdowns, since department-store boots often drop after the holidays.

What is the difference between the black and dark tan?

Only the color. Both use the same leather upper, wingtip toe, lace-up closure and rubber outsole. Black is the safer choice for dressier outfits; dark tan shows brogue detailing more clearly.

What is the heel height and shaft height?

The listing gives an ankle shaft height and a block heel but no exact measurements. Expect a heel in the roughly one-inch range typical of men's dress boots. Check the product page for exact figures before ordering.

Can I wear these in rain or snow?

Light rain is fine thanks to the rubber outsole. They are leather ankle boots with no waterproof membrane, so heavy rain or deep snow will soak through. Treat the leather with a protector and avoid slush.