Beauty & Fashion

Style Boots

So many cute boots to choose from, so many ways to wear them wrong.

What’s a girl to do?

When it comes to boots it’s all about proportion. That means getting the height, cut and length of your boot to balance, not match, not offset, not augment, but balance with the length of your dress, skirt or pants.

Here are a few tips …

The ankle boot: I am die-hard fan of the ankle boot (also called “booties” when they hit just below the ankle bone and “shooties” when they rest well below the ankle but lay over the top of the foot).

The right one can be worn with pants — cropped or long, wide, baggy or skinny — or dresses and skirts, including the circle, bubble, A-line, mini and pencil. Below is a little sample of outfits for every occasion that I think works well with my fave bootie of the season

The key to the ankle boot is to make sure there is enough leg showing between the top of the boot and the bottom of the skirt or pants. Otherwise your legs will look short and stumpy. The heel should be high because it is a rare girl who can pull off a flat bootie with cropped pants or a skirt.

Knee-high boots: These boots can be casually rustic or sleekly equestrienne, adorned with buckles and straps or a simple column of shining leather, grounded with a wedge or teetering on a spike. Whichever you wear just make sure that the top of the boot comes to the bottom part of your knee (not over, that’s a different boot.)

If you’re wearing them with a skirt or a dress, you can cover the top of the boot with the hem of the skirt. Otherwise have no LESS than 3 inches of leg showing. In the event that your skirt merely skims the top of the boot and you risk having less than 3 inches of leg showing, wear a matching or complementary colored tight to bridge the gap.

See how well it works on my friend Rebecca here?

Over-the-knee boots: Sometimes known as “rocker” or “pirate” boots, these look best with skinny jeans, floaty mini dresses and big circa 1960s Bridget Bardot hair. But for dresses or skirts, “mini” is key here to achieve that ideal “3-6 inch gap” between boot-top and hem. Oh, and you better have the legs to pull it off.

Thigh-high boots: Arguably this year’s hottest boot (but, if you ask me, not the one with the most staying power). This boot is not for the faint of heart or the short-legged. If you carry your height in your torso, stick with ankle, knee-high or over-the-knee. But if you are one of the lucky ones with more leg than you know what to do with, go for it.

I like thigh-highs with styles that counteract the stripper-y vibe of the boots, so I chose a cute cotton dropwaist dress with a nautical attitude and leggings for day and a hot pink cocktail dress for night and grounded both outfits with a versatile plaid boyfriend jacket:

Calf-high boots: These boots work best for shorter women and, in my opinion, should only be worn under pants because they can cut your leg in an unflattering way. I like to pick a boot with a cute toe that looks cool peeking out from under my bootcut jeans (I’m a purist when it comes to jeans. Though I will wear skinnies, I think the best, most flattering is a boot-cut jean)

I go for toes that are uber-pointy or — my favorite — the squared-off pointed toe of a cowboy boot. Also, consider a kicky colored boot as an accent, yummy burnished leather or an embellished toe.

I’m also a stickler for proportion here. The “break” of the hem of my pants should cover the top of the boot up to where the toe begins and should reveal the tiniest sliver of a heel in the back. Pants that hover above the boot to reveal the whole foot always look way too short to me.

A few more tips:

The inside heel of a boot should have a little wiggle room to avoid rubbing.
A basic boot wardrobe (yes, even here in California) should include one tall (knee-high) dress boot in black or a neutral color that works with your wardrobe and one tall casual boot for wearing under or over jeans, with leggings or with flouncy skirts. This boot can be heeled or flat, but if you get “tall” boots in both work- appropriate and casual styles, a lot of the guesswork about what goes with what will be taken care of.
Pay as much as you can reasonably afford for your basic boot wardrobe (and shop sales!). Get as simple and classic a line as you can find. That means neutral colors, a heel that is neither too chunky or too spindly and a toe that is neither too of-the-moment pointy or too grandma-shoes square. Then with proper care, the boots can last for years and become a genuine investment.

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