One of the most common styling questions I get both on social media and one-on-one with clients is how to do the whole ankle boot-tights thing — particularly for the office. First and foremost, not every ankle boot is meant to go with dresses and skirts. Some that mimic the cowboy boot heel are really meant to be paired with jeans.

Exhibit A: Don’t do this ankle boot with tights and a dress. This style is really meant for denim.

With a dress or skirt look, you want an ankle boot that mimics a pump. You can do one with a stiletto-type heel or a block heel. Exhibit B:

The most flattering and polished way to do the tights/ankle boot combo with a skirt or dress  is to match your tights to your shoes. Not that you can’t rock purple tights with red ankle boots if that’s your thing. But, most of our clients are looking for classic, purposeful, difficult-to-go wrong combos that work for their daily professional  lives. And if that is one of your style requirements, go black on black following a few simple rules:

1.) Wear opaque black matte tights; avoid any sheen to your tights that draw attention and add volume.

2.) Suede black ankle boots work better than a shiny leather. The matte-on-matte slims and lengthens the leg line.

3.) Opt for a pointy or almond toe for a polished look that mimics a pump.

4.) Look for an ankle boot that has a low vamp or cuts down into the ankle/foot instead of coming up high toward the upper ankle. This is the most flattering since higher the shoe comes up on your leg,  the shorter your legs look.