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Q. While I know every trend I like is not for me, I am enamored with ankle boots paired with skirts (particularly pencil skirts) for work. I am 5 feet 3 inches tall and curvy, and my legs are of course short. Can I pull off this look? Also, should I look at boots that hit right at the ankle or those that come a bit higher?

A. The most flattering way for a petite curvy woman to wear ankle boots with a pencil skirt is to look for ankle boots (or booties) that dip down in the front, showing off more of your leg. Avoid any booties that come above the ankle bone. Look for slim heels, rather than chunky heels, to offer a more flattering look for your legs. Also, it’s best to pair them with skirts that hit above your knees, or right at the top of your knees, to help elongate (and visually slim) your legs. Here are some booties worth trying:


Q. I am looking for a stylish, summery, comfortable, flat work shoe that can be good for lots of walking (tours) and be good in the dirt of the garden (garden tours). Some ideas are: metallic tessa clogs, minnetonka loafers, flat espadrilles….anything come to mind that would be a winner?

A. It sounds like you need a comfortable, chic flat that can withstand a lot of walking and perhaps dirty or muddy conditions. The clogs you mentioned are certainly an option, but Minnetonka loafers and flat espadrilles are not ideal for walks in the garden as dirt will cling to the surfaces of the shoes, making it difficult to remove. Your best bet is to look for a flat or low wedge with a rubber sole that will provide comfort and a washable barrier for dirt. Boat shoes are made for outdoor living and come in a great variety of prints and colors, making them a great option for walking tours. A comfortable, yet sturdy, sandal is also an option if your job allows it. Here are some styles to help you get started with your search:

Q. I would love some help finding cute sandals that are not the usual thong-style. I have slight bunions and feel uncomfortable wearing the thong style that seems to be the most common option for sandals.

A. Sure! We found a selection of seriously stylish flat sandals with strategically placed straps to help minimize the visibility of your bunion. No thong styles included! (Another option is to try one of this summer’s must-have flat espadrilles.)

Q. Help! I’m going to a wedding (2 weekends from now ) in NYC and am having trouble finding shoes. Seems like there are wedges everywhere, but I need dressy black heels. One place suggested a wedge, but for a wedding? Any suggestions would be great.

A. I love a good wedge, but it’s not my favorite choice for a dressy affair. I agree that a sexy black heel is your better option for a NYC wedding. Here are some dressy black heels for you to choose from:

Q. I am not a logo person by any means but have always been drawn to the Tory Burch Reva Flat. I wear flats to work most days and I’m trying to decide if I want this shoe to be my next purchase. Would you consider the Reva Flat to be a ‘trend’ or more of a classic style staple?


A. The Tory Burch Reva Flat has definitely moved into “classic shoe” territory — no longer a trendy must-have, this iconic shoe is one that you can wear for years. That being said, if you have always been drawn to them and can afford the $195 price tag, then enjoy wearing them without worrying whether they are trendy or not. The tricky part now will be deciding which of the many versions available to choose!

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