We’ve just come back from a two week trip to Hong Kong and as always, I’m very inspired by the street style we saw. Women wear jeans less frequently, favouring trousers, skirts and dresses of all descriptions, and black leggings in particular. I saw leggings worn under mini dresses, midi dresses, tunics, straight skirts, flared skirts, cropped pants, harem pants, short shorts, long shorts and culottes. The combinations worked exceptionally well for some good reasons:

  • Leggings are practical and comfortable in mild temperatures. 
  • They can be worn with any heel height, especially flats and low heels which are essential in a city where most people commute by foot and public transport.
  • Their sleek silhouette adds instant structure to an outfit.
  • Leggings can make an outfit more interesting, creating that extra bit of drama.
  • They are easy to match with black footwear, which extends the leg line.

To my eye, leggings look best in black and worn with a neutral support act. They can be cotton-rich, pleather, or mixed media, depending on your preferences. Black leggings also complement women with black hair or partially black hair, creating a sense of natural balance in an outfit. Of course, you don’t need to have black hair to wear leggings with panache, but repeating black in the outfit helps to create a cohesive look. 

Leggings worn with flowing and oversized tunics and dresses with asymmetrical hemlines like the two examples below are a fabulous combination and I saw a lot of this in Hong Kong. The uneven hemlines and extra length of the tops are key to creating a more dramatic effect. Visually, the uneven line of the hem draws the eye upward and vertically creates a flattering effect. I preferred the combinations with woven tops and knitwear, as opposed to knitted tops made of jersey because they created a more luxurious look. Keeping the outfits neutral does seem to add a sense of chic to an otherwise very casual bottom.

DONNA KARAN Stretch Crepe Leggings Style PantsVince Poncho & Leggings

Tunics that are shorter and less oversized, like the next set of examples, are probably more wearable, but the visual effect is less dramatic. That said, it’s a good look that can be made more dramatic by wearing interesting black footwear. Think cut-out booties, peep-toe booties, ankle strap heels and flats, d’Orsay styles, cage heels, mules, upscale sneakers, flatforms, pointy toe slipper flats and monk strap oxfords.

Karen Kane Asymmetrical Hem Bateau Neck TopAllen Allen Slub Knit V-Neck Tunic

Eileen Fisher Merino Jersey Tunic DressSejour Colorblock Tunic Sweater with Removable Cowl NeckPotter's Pot Print Kimono Jacket

I also like the idea of adding black leggings to high-low maxi dresses like the ones shown here, thereby taking the look from a frock to a trouser outfit.

Anthropologie Acanthus DressAnthropologie Onyx Maxi Dress

Here are street style pins of leggings outfits for more inspiration: 

Remember that a pair of black denim jegggings or Ponte pants will substitute for a pair of leggings if you prefer wearing a more substantial pair of bottoms. 

I used to wear leggings in the ‘80s, and had another go at it about eight years ago. I enjoyed wearing zippered black leggings under woven dresses and pencil skirts because it was comfortable, warm, and turned the look into a trouser outfit. As long as I could keep the outfit somewhat soft and very crisp by combining leggings with dressier woven tops (and sometimes jackets) in luxurious fabrications, I loved the look. I’m inspired to create similar combinations again because leggings provide an alternative to jeans, and make skirts and dresses more wearable when it’s not quite warm enough to bare my legs. I’ll start off by popping a pair of black leggings under some of the dresses in my closet, and see how it goes. 

Over to you. What’s your relationship with leggings, and would you wear any of these combinations?