Q: I bought a leather-jacket-type vest, but I have no idea what to wear it with. I like the rock-and-roll vibe, but I don't want to look like I belong on the back of a Harley. How can I make it more girly?
A: By definition, this style of vest will never be girly, but the rest of your outfit can be. In fact, a leather vest is the perfect item to toughen up an otherwise feminine look. However, it is critical to consider proportion when wearing a leather vest. It looks best with tops that have high necklines, but almost any pant can work. It can also be worn with dresses and skirts—just try to avoid apparel with lots of volume.
VEST $298, Victoria's Secret; victoriassecret.com.
DRESS $228, Leon Max Collection; maxstudio.com.
Q: I am transitioning my wardrobe from that of a bartender to something more professional. The issue is that I have fairly large tattoos on both of my feet. I want to wear a chic and simple pointy-toe heel but need something with more coverage. I cannot find anything!
A: Your question is very timely because I've been working with another individual with the same challenge. Together, we found a very stylish and on-trend solution: a pointy-toe ankle boot. This style works perfectly with pants and skirts, is available in a variety of colors and surface treatments, and can seamlessly transition from day to evening. Let me also suggest that you consider makeup or tights as a cover-up. Few looks are more sophisticated than an LBD with black tights and a black heel. Good luck!
BOOTS $1,575, Pierre Hardy; pierrehardy.com.
WRITE OR WRONG
Q: One of my best friends from college is having a book celebration in Chicago. It is a reading, party, and networking mixer. Is a little white dress professional enough?
A: I appreciate knowing the full context of your friend's celebration because I was initially inclined to say, "Who cares? Wear the white dress!" But then I thought, Would I wear a white suit to a job interview? No. It's still a celebration, so wear something upbeat yet professional. Think about enlivening more conservative silhouettes with vibrant color and patterns. In my experience, few options work better than a classic wrap dress. (Thank you, DVF!) Enjoy!
DRESS $485, Diane von Furstenberg; (646) 486-4800.
Photographs courtesy of the designer, Studio D, WireImage and Getty.