Personally, I have always enjoyed the look of flat oxford shoes. To quote hubby Greg: “They are VERY cute”.  But there is no doubt about it: flat oxfords shorten the leg line and look masculine because they are flat shoes with high vamps. Unless you have a proportionally long leg line they aren’t the easiest shoe to wear.

With some experimentation you can balance out the masculine vibe and shortening effect. Here are some things you can try:

• Pair them with tapered pants, jeans or ankle length leggings: Showing off the entire shoe when wearing pants, jeans or leggings somehow makes them look more feminine. When sporting perfect pant lengths with wide legs or bootcuts, the tips of the shoe peek out while the rest of the shoe is covered. This looks more masculine to my eye. Of course, the masculine look might tickle your fancy so by all means wear flat oxfords with wide hemmed pants if you prefer that visual effect.
• Reveal skin on the foot: Sometimes, allowing a bit of skin to peek through between the vamp of the oxford and the hem of the pants keeps things feminine. That’s why I like to go sock-less when I wear my oxfords with tapered jeans. Although it shows more skin, I do not cuff my jeans when wearing flat oxfords because the horizontal cuffs and finished length of the jeans are too leg shortening for my tastes. Instead I leave my skinnies scrunched.
• Raise the hemlines of skirts, dresses and shorts: This visually lengthens the leg line. I’m not one to wear short hemlines, but a couple of inches above the knee works well. Baggy short shorts work particularly well with flat oxfords because they showcase most of the leg.
• Voluminous pieces: Unstructured items complement the look of flat oxfords. It’s not a slam dunk, but short sack dresses, breezy blouses, boyfriend cardigans and baggy boyfriend blazers like to be paired with flat oxfords. Somehow, surrendering the waistline is key.
• Cropped jackets: Boyfriend blazers work beautifully with flat oxfords when worn with tapered jeans, but cropped jackets work well too. Wear a cropped jacket over a flared skirt or dress, tapered pants or with walk shorts. The short hem on the jacket visually draws the eye to the waistline which raises the line of the leg.
• Add hosiery: Keeping a low contrast between the colour of your legs and the shoes creates a longer leg line. For example, wearing black opaque tights with flat black oxfords is visually lengthening because there is no contrast between the oxfords and the leg. Wearing black micro fishnets with my oxfords keeps the contrast low too.
• Choose a low contrast shoe colour: Sometimes, opting for nude, metallic, light grey or light brown flat oxfords works better with dresses and skirts because there is low contrast between your leg colour and the shoe. It can also soften the integrity of the shoe, making it more feminine.

A combination of these tips will also work in an outfit. It’s really up to you and your figure flattering priorities. If you like to keep a long leg line as I do, these tips will help. If sporting a shorter leg line works for you, wear flat oxfords with just about anything.

Although flat oxfords are an acquired taste, adding them into your current wardrobe mix can change up the look quite dramatically. They bring both an arty and an androgynous element to your style, which can be appealing. And the comfort factor is pretty compelling too – after all, my flat oxfords saved my feet at Fashion Week!

You might remember these outfits from my recent Fashion Week posts. And that’s forum member Tara peaking over my shoulder in the first picture. Adorable!