I was all over flat oxfords when they re-appeared on the fashion scene in 2008 for three reasons. First, I wore flat white oxfords to death in the ’80s, so it’s a nostalgic and fun style to wear the second time round. Second, I love the look of refined menswear inspired footwear thanks to my tomboy style gene. And third, I’m always interested in closed flat shoes because of their high comfort factor. 

Five years ago, flat oxfords did not get much love from my clients or from our readership. Many liked the idea of the style but were stumped as to how to integrate them into their outfits. I suggested guidelines on how to wear flat oxfords, but still the reactions were very mixed. The challenge was the same: how NOT to look and feel dumpy, stumpy, short legged, flat footed, and masculine.

A laceless version of the flat oxford came out a couple of years ago, which seemed a little more feminine. That style won over more of my clients and our forum members. Availability in softer colours like taupe, nude, blush and light grey also made a difference. 

Now that ankle length and cropped pants are just about the biggest trend on the planet, flat oxfords are gaining even more popularity. Matching them with on trend rolled up boyfriend jeans is another fashionable way to wear the masculine ped. But truly, matching flat oxfords with just about any bottom these days — skirts, dresses, shorts and trousers — is perfectly acceptable. The outfits below show the versatility of the flat oxford across a variety of colours.

I enjoy wearing flat oxfords and just replaced my black and white pair that I walked into the ground. I bought Cole Haan’s Skylar Oxford in mirrored metallic, and couldn’t be happier with them. I like to wear flat oxfords with skinnies and tapered trousers best, both cropped and full length, and always sans socks. I like to showcase the entire shoe and see skin coming through the top of the shoe, which means no socks. That’s what keeps the vibe feminine to my eye. Of course, I can cheat by wearing nude hosiery and knee-highs so that it looks like I’m not wearing socks and still keep my feet warm. 

I’m interested to hear whether, after five years, flat oxfords look better to your eye, especially since wearing high vamped footwear has become completely mainstream. Do you still feel stumpy, dumpy, frumpy and masculine when you wear them? Or do they look fashion forward and flattering?