Some of my clients wear leggings as an alternative to jeans, Ponte pants or corduroy skinnies. They are ultra comfortable, an easy pull-on-and-go, great for travel, versatile, and a way to change up your look. It’s no wonder that leggings have become a mainstream fashion staple with lots of staying power. 

Looking and feeling overly casual is a concern when wearing leggings, which is fine if that’s your style goal. But if you’re after a dressier look, you need to be deliberate about the support act. Here are some tips to get you started:

  • Choose black leggings because they’re the easiest to style and look the dressiest.
  • Choose dressy black footwear, flats or heels, to wear with the leggings because the colour repetition pulls together the look. 
  • Keep the the rest of the outfit NEUTRAL and either high or low contrast to the black leggings. 
  • Pleather black leggings add texture, shine and hard edge to an outfit. Sueded leggings are another option. 

The photos here provide good examples of smart casual leggings outfits.

Leggings & Tunics 

The outfit on the left combines a chunky and architectural tunic sweater — a poncho or sweater coat is fab too — with leggings, dressy black and grey loafers, and a black bag. The outfit on the right combines a dressy woven dress or tunic with pleather leggings and pointy toe flats. The dressy footwear is important, which means that black pumps or dressy booties work too. The streamlined simplicity, neutral colours and substantial fabrication of the tops go a long way to making the leggings look chic.

DONNA KARAN NEW YORK Cashmere-blend LeggingsTHE ROW Moto Leggings

Skirted Leggings & Roomy Knitwear 

Create skirted black leggings with an all-in-one style, or wear black leggings under a woven black pencil or A-line skirt. The latter can feel bulky on the midsection so make sure you’re comfortable with the layering. Combine the skirted leggings with a short, boxy pullover like the outfit on the left, or with a regular length high-low pullover like the look on the right. Finish off the outfit with dressy black flats like oxfords, loafers, d’Orsay flats, pumps, shooties, or Chelsea boots. Top off the outfits with a neutral topper like a moto jacket, trench coat, peacoat, man coat, cocoon coat, or trapeze coat.

FORME D'EXPRESSION Skirted LeggingsRAG & BONE Kristin Leggings

Lyseé leggings are a cut above the rest because they provide genius girdling support but do not give you muffin top. The fabric is substantial, it launders well, and there are many styles to choose from. Comfortable and well worth the price.  

A good few years ago I used to wear black leggings under black or patterned woven pencil skirts with dressy pumps. I loved the look back then, but haven’t worn the combination in ages. Perhaps I’ll give it another try in black and ink, since I enjoyed sporting my ink flag dress with leggings and pointy toe flats in the Summer time. How about you? Do these outfit combinations appeal to you?