LEATHER CHUKKA
#5. Steve Madden Men’sBronxxx Chukka Boot ($68 @ Amazon.com)
Like a spoiled (but stylish) brat, this shoe takes from its more casual brother, the desert boot or chukka, which usually comes in suede. This version is dressed up in just enough leather to make it an all-purpose (and comfortable) option when you’re not sure where the day will take you. Country club or strip club? Doesn’t matter. Keep in mind, though, that this shoe is the least dressy of those listed here and it’d be in your best interest to avoid matching it with anything more formal than business casual.
BIT LOAFER
#6. Stacy Adams Easton Bit Loafers ($80 @ Amazon.com)
A staple of the preppy wardrobe since its inception in the 60’s, the bit loafer provides a great alternative to the penny loafer, with a flash of hardware across the vamp (shoe speak for “top”; shoe speak insists on making us feel stupid for sport). Here’s the thing: Dress loafer slip-ons are acceptable now to wear in business situations, with dress trousers or tailored dark denim, and these bit loafers add a bit (get it?! Okay, I’ll see myself out) more flair to an everyday work look.
