I mentioned in my post about Fall & Winter 2015 trends that booties with higher shafts are the fashionable choice, and will be trending strongly for a while. Note that a bootie with a higher shaft measures an inch or two above the ankle bone, so taller than regular ankle boots but not as tall as mid-calf boots. 

Booties with higher shafts can be paired with just about any outfit these days, the silhouette is that versatile. But there are four ways to wear them that are quite straightforward. 

Heeled With Cropped Jeans or Pants 

The cropped pants and jeans trend complements the high shaft bootie trend to perfection. Wear your booties higher and your bottoms shorter. Show a slither of skin between the booties and bottoms, or insulate the skin with a low contrast sock. Wear nude-for-you knee highs if you want to “show a slither of skin” but feel insulated, (my favourite bootie trick of all). 

Create a column of colour, or at least keep the contrast between the bottoms and the booties low to create a longer leg line. Feel free to create a high contrast between the bottoms and booties too. You might want to tuck the top to further elongate the leg line from the hips up in that case, but it’s not essential. These photos provide good visuals for the variations.

TOD'S Laser-cut Leather Ankle BootsSAM EDELMAN Edith Leopard-print Calf Hair Ankle Boots

JIMMY CHOO Mass Suede Ankle BootsNEWBARK Sabrina Snake-effect Leather Ankle Boots

Flat With Cropped Jeans or Pants 

Feel free to combine FLAT high shaft booties with cropped pants and jeans. Show a slither of skin between the booties and bottoms or insulate the skin with a low contrast sock. Visually, I prefer seeing a slither of leg skin, which can be insulted with nude knee highs. 

If you’re concerned with feeling short in the leg, keep the booties and bottoms the same colour as shown in the example on the left. Creating a shorter leg line with high contrast flat booties and jeans, as seen in the example on the right, can be offset by tucking the top which lengthens the leg line upward from the hips. 

ISABEL MARANT Roddy Leather-trimmed Suede Ankle BootsAQUAZZURA The Heilbrunner Shearling-trimmed Velvet Boots

With Mini Skirts 

Wear flat or heeled high shaft booties with a short skirt or dress. The short hemline on the skirt or dress lengthens the leg line upwards from the knee, offsetting the high vamp of the booties (and their lack of heel if you’ve chosen flats). Create an even longer leg line, as seen in the example on the right, by wearing a bootie that is low contrast against the skin tone.

RUPERT SANDERSON Hamilton Leather BootsSAM EDELMAN Louie Fringed Suede Ankle Boots

With Midi Skirts 

The proportions of midi and high shaft bootie are easier to achieve with a naturally long leg line, and/or high-heeled booties. Culottes work as well for the look when they are at the midi length. 

The vertical integrity of a column of colour combined with high shaft booties in the same colour — as seen in the example on the left below — creates a unified whole because there isn’t much space between the hemline of the skirt or dress and the top of the bootie. The eye is drawn up and down without a break because of the intense repetition of the colour. 

Conversely, the example on the right shows high shaft booties that are high contrast to the column of black, yet the result is as flattering. That’s because the booties are high heeled and low contrast to the models skin tone, which lengthens the leg line downwards from the calf.

SAM EDELMAN Bryton Leather Ankle BootsMAISON MARGIELA Glittered Leather Ankle Boots

Of course, these are merely guidelines that will get you started. There are countless other ways to incorporate high shaft booties into outfits that look just as fabulous. If you are stuck, feel free to ask questions in the comments section.