What to Wear with Leggings

Leggings are everywhere you look—bus stops, museums, restaurants—women of all ages are wearing leggings tucked into boots and topped with winter coats. And no wonder, who doesn’t love a pair of black stretchy, comfy leggings? So easy to slide into winter boots, and then swap with a pair of flats once you’re indoors. Leggings feel like you’re wearing pyjamas. But what to wear with them? How do you dress them up for work or dinner out? Especially if you’re older or rounder?

Here are some ideas from my sketchbook.




# 1: Go Long

You’ll need a top that’s long enough in the back to cover your derrière, and long enough in front to cover the crotch area. (You know why.) Not a dress—that rarely looks good because the proportions are off. Your best bet is a tunic top. Tunics are designed to be worn with leggings: not too short, not too long. Perfect to wear to work or an informal dinner.

 # 2: Find the right shape and length

Chunky, boxy knitted sweaters may look great on tall, thin models, but they make the rest of us look dumpy and fat. To make matters worse, most sweaters are cut straight on the sides, resulting in a figure-hugging look, which has a tendency to highlight any defects or extra curves.

The trick is to find a shape that works well with your figure. You need something with clear visual lines and some semblance of structure. A tunic top that skims the parts of your figure that you want to show and minimizes the rest. Unless you are Robin Hood wanting to show off a set of powerful thighs, you will want a tunic that ends somewhere between the crotch and mid thigh. As with a mini skirt, the taller and thinner your legs are, the higher the hem line can go and still be flattering. When in doubt, look for an A-line shape that fits at the shoulders and swings down and out from there.


#3 Keep it chic

The best winter outfits allow you to show some skin, without sacrificing body warmth. Tunics with a transparent layer—lace, gauzy chiffon, silk—work really well. They will keep you warm and still looking chic, delicate and feminine. They offer a little more modesty without making you look like a tent. They hide many a surface flaw (scars, blotchy skin, a few extra pounds) without anyone being the wiser.

Transparency adds an air of mystery, and makes you look more like a woman and less like a schoolgirl.


#4: Find the right fabric

Patterns are more forgiving than solid colors. Particularly random patterns, rather than rigid ones (checks, plaids, stripes) which tend to distort and amplify any extra curves.

Don’t go near any shiny fabrics. Shine works best as an accent than an all-over effect, so keep it for your shoes, bag, jewelry, hair accessories.

Darker colors —navy, espresso, forest green—are kinder than lighter colors, but all black will drain your face of color and make you look like a widow. If you must wear black, add some bright color with your winter hat, scarf, gloves, bag.

‘Bond Girl’ Fashion Ideas

Who doesn’t love comfy-chic clothes that can be worn more than one way? These two outfits go beyond the average day-to-evening with a look that you can change in seconds. Talk about convenient!

These ensembles were cooked up by designer Hussein Chalayan.


Either one would shine in an action movie. Can’t you just see a character in the next James Bond 007 film effortlessly transforming and revealing some secret weapon/document/prop without breaking stride? (Here’s some Bond music for atmosphere…)


Similar mechanics were used for Cinderella’s transformation on Broadway:

Finding the Perfect Summer Maxi Dress

I’ve been looking at summer maxi dresses for awhile, but most of them are just completely impractical (spaghetti straps) or unflattering (voluminous tent) unless you are a size 2.

However, I recently stumbled upon a great post by style expert, Deborah Boland, that featured some incredibly flattering ones. I decided to do a deep analysis of why they work. See if you agree.

Helen of Troy


Empire waist + deep V neckline = a winner.


Flattering from both front and back.

You will indeed feel as graceful and beautiful as Helen of Troy in this Grecian-inspired number. (The Ancient Greeks knew a thing or two about draped fabrics and hot weather.) It’s comfy, chic, versatile and flattering: the Holy Grail for most women!

I love this dress because It gets absolutely everything right:

  • pretty blue color
  • the pattern is a low-contrast motif, so it doesn’t overpower the viewer, yet still offers some camouflage for those extra curves
  • deep V in front and back to show some skin, yet still leaves something to the imagination
  • V-neck makes the waist look smaller
  • straps wide enough for a real bra
  • empire waist with a flat band around upper cage to maintain a feminine silhouette
  • soft jersey fabric that is heavy enough that it doesn’t pouf out (like cotton would) where it’s gathered but instead flows down smoothly over the tummy (without grabbing it)
  • enough pleating in the tummy area to allow you to eat whatever you want and sit comfortably
  • falls straight down from the hips—very helpful if you have heavy thighs
  • flares out at the feet so you can take real steps versus feeling like you’re wearing a restricting kimono
  • ankle-length means you can wear flat sandals or heels and it works
  • no ironing – perfect for travel!

Genius all around.

The only thing I would add is maybe a semi-sheer long-sleeved bolero cover-up/wrap to ward off the evening chill.



maxi2Another great maxi is this one, which has many of the same features as the one above. In addition it offers:

  • cap sleeves that flatter plump arms, and make the waist look slimmer in comparison
  • a modern square neckline enhanced by a faux V-neck look, courtesy of the piping on the bodice
  • an empire waist to flatter rounder figures, with a tie at the centre to draw the eye up
  • comfy, stretchy viscose fabric
  • a pattern that is bold, vibrant and fun, without overpowering the woman wearing it
  • a darker background color for a more slimming and sophisticated look that can be worn day or night

This would be a perfect choice for dinner al fresco, or drinks at the yacht club. Or even attending a casual beach wedding. Bridesmaid’s dress, anyone?

So if you’re looking for something comfy-chic to throw on for drinks by the pool or just to run to the store, the maxi dress can indeed be your new best friend… just be sure to choose wisely.