All Saints Olvera Long Leather Skirt in Deep Slate, $468; Milly Leather Bell Skirt in Camel, $725; Zara Leather Effect Long Skirt, $79.90; J Crew Covered Button Crepe Blouse, $98; Jimmy Choo Agnes Black Suede Pointy Toe Pumps, $595; Malene Birger Klein Gold Plated Necklace, $395; Tod’s D-Cube Bauletto Piccolo leather tote, $1,925.

To wear or not to wear leather at work—that is today's fashion brain teaser. While old-school adherants would probably shun the idea altogether, that may not be necessary in some of today’s more laidback, modern work environments.

Corporate offices have different standards from fashion or other creative businesses, which is where the lines get blurry. Leather pants might be completely inappropriate for a law office. A junior employee in an interior design firm, on the other hand, could probably easily pull off a cool pair of leather joggers with some pointed-toe booties and a cashmere sweater.

The general consensus is that the more senior one is in an organization, the more leeway one has. A queen bee can do no wrong, within reason. But a young staffer still trying to earn her stripes should tread carefully.

With all this in mind, there are a few general rules that will ensure your weekday leather doesn’t veer into S&M territory.

• Keep leather skirts below the knee.
• Opt for other colors than black. Tan, brown, burgundy, green, blue, yellow, orange—anything is less aggressive than black leather.
• Boxy or loose cuts are more directional and less overtly sexy.
• Balance edgy leather with classic accessories. Think ying and yang.

Alexander Wang Leather Peplum Top in Blue, $1,095; T by Alexander Wang Raw Edge Crop Top, Marigold, $650; BCBG Beata Short-Sleeve Oversized Top in Camel, $228; ManoloBlahnik Pointy Toe Pump, $695; Ann Taylor Long Pencil Skirt, $79; Tamara Mellon TM Love Large Leather Tote, $1,095; Eddie Borgo Cyprus Gold Plated Earrings, $200; Nars Audacious Lipstick in Oxblood Burgundy, $32.