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How to Wear Dresses with Flat Footwear

Richard Wright

Gone are the days when heels higher than an inch was the best footwear option for dresses. In fact, these days it’s more fashion forward to pair flat footwear with dresses and skirts.  Plus, flats or heels of an inch or less can effectively dress down an outfit. It’s unexpected, refreshing, and for many an extremely comfortable option. 

The outfits here showcase an assortment of dress silhouettes with an equally large assortment of flat footwear styles. These examples are by no means exhaustive, but they are a good base to work from. Some pairings are a lot more wearable than others because they create conventionally flattering proportions by elongating the leg line.

FLAT SANDALS WITH SHORT HEMLINES

Vince Bracelet Sleeve DressHELMUT LANG Draped Jersey Dress

Pairing flat sandals with shorter hemlines is the most wearable option because the combination makes your legs look longer. Showing part of the kneecap is ample skin, and there is no need to show more if shorter lengths are not your thing. Wearing low contrast sandals further lengthens the leg line, thereby offsetting “that stumpy feeling”. Bookending the colour of the sandals with your hair is another slam dunk that grounds the look. Curved hemlines visually elongate the leg line even further.

FLAT SANDALS WITH KNEE-LENGTH HEMLINES

Nightcap Clothing Crochet Hanalei DressETRO Printed Silk Shirt Dress

Wearing a longer hemline with flat sandals can feel a little short-legged but there are ways to overcome that. Try wearing a dress with a high-low hemline, or again, create a low contrast between the colour of the sandals and your skin tone. Both strategies make the lower leg look longer while wearing a longer hemline. 

FLAT SANDALS WITH LONG HEMLINES 

SPELL White Dove Vintage Lace Maxi DressISSA Maya Printed Silk DressDONNA KARAN Draped Stretch Crepe Midi DressRICK OWENS LILIES Stretch Jersey Midi Dress

Preventing the short-legged feeling with midis and maxis can be overcome in two ways. Wear maxi lengths with side vents to give the illusion of a shorter hemline. This is especially effective as you stride because the vent opens to expose leg skin. Wear midi styles with asymmetrical hemlines because the broken line of the hem adds structure to the leg. That’s why the straight hem of the midi skirt in the bottom right corner looks the most “stumpifying”. It’s a fashionable look that requires a relatively long leg line to look more proportional.

LOAFERS AND D’ORSAYS WITH SHORTER HEMLINES

CARVEN Seersucker Wool Blend DressMiH The Knot Front Dress

These examples showcase high-vamped footwear with an assortment of dress lengths, which are the trendiest combinations at the moment, and the toughest to pull off. The exposed foot skin of sandals helps elongate the leg line because “skin equals structure”. High-vamped footwear shortens the leg line. To some extent, you have to be at peace with the shortening effect of high-vamped footwear. 

The principle is the same. A shorter hemline offsets some of the stumpy factor of the outfit, and half a kneecap is ample skin if short hemlines aren’t your thing. Pointy toed flats also help elongate the leg line. Dress silhouettes that are cut fairly loose prevent the hem of the skirt from riding up to a shorter length.

SNEAKERS AND BIRKENSTOCKS WITH DRESSES

RAQUEL ALLEGRA Shredded Spray Dye Cotton Blend Jersey DressTOTEME Belize Knitted Jersey Midi Dress

It’s extremely fashionable to pair sneakers with dresses, which we discussed at length a few months ago. Pairing Birkenstocks with dresses is just as fashionable. In both cases the point is to create proportions that are just flattering enough, instead of striving for conventionally flattering proportions. 

On the left, the asymmetrical hemline and visible kneecap elongates the leg line. On the right, the side slit creates leg exposure which visually lengthens the leg line. The repetition of white in both the top and bottom parts of the outfits creates a cohesion that pulls the outfits together.

FLAT OXFORDS WITH DRESSES

ACNE STUDIOS Lash Oversized Cotton Poplin Shirt DressACNE STUDIOS Dita Turtleneck Wool Sweater Dress

Flat oxfords are a very stumpifying shoes that intuitively seem a bad choice for dresses, especially if they are in a high-contrast color to the skin on your legs. It’s much easier to create flattering proportions with heeled booties than flat oxfords. I’m voting this combination as hardest in this list, yet it’s also the most fashion forward and interesting.

The shirt dress on the left creates slightly more flattering proportions because of the curved hemline and visible kneecap. The outfit on the right is more shortening, even on a tall leggy model, because of the straight hemline and longer length of the dress. But at the moment this look makes the more fashion forward statement. Who knows, perhaps we’ll all think it looks flattering five years from now.

Wearing flat boots and booties with dresses is another option, and one I’ll cover at a later date. In the meantime, I’m encouraging all my clients to continue wearing their dresses with heels, but also to experiment with flat footwear. Manipulating trends so that we can be fashionable and comfortable is part of what is so liberating about modern fashion. 

I LOVE wearing dresses with loafers, sneakers and lace-less flat oxfords, and have been doing so for weeks in our stunning Summer weather. My dress lengths are either just above or just below my kneecap, and the footwear is either white or silver, so low contrast against bare leg skin. At the moment, these combinations are my favourite way to wear warm weather dresses. Relaxed, modern and sans sandals.

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