What to Wear with Brogues and Oxfords


I bought my first pair of brogues back in the late 1980s, they were the fashion trend at the time – but with a long pointy toe (not quite a winklepicker but heading that way).  My next pair arrived into my life in the early 1990s, a rounded toe, and traditional decorative perforations.  A third pair, these ones were high heels and I’d wear them out clubbing and dance the night away in them (then hobble home afterwards).

Brogues and Oxfords have been back in fashion the past few winters and as they bring comfort and style to a winter wardrobe, this classic shoe style is a great one to include if they appeal to you.

Now that my shoes have to accommodate orthotics, my brogues are ones that happily do this and are getting a good workout.

What to Wear with Your Brogues?


Simple and easy – you can cuff the jeans or wear a cropped jean too to expose your ankles and wear the brogues with a sockette that doesn’t peep over the top of the shoe for a modern streamlined look.

What to wear with brogues and oxfords

If it’s too cold to show any skin, you can add a sock either in a fun pattern or one that blends with your shoe.  These were from Clarks a couple of seasons ago.

How to wear brogues - and what to wear with them

And when it’s cold outside a sock that blends with shoe and jean is the easiest way to go!   These suede orthotic friendly oxfords are from Ziera.


Wear with an Above the Knee Skirt or Shorts

What to wear with brogues and oxfords

The easiest way to wear brogues or oxfords with a skirt is to choose one that ends at or above the knee.  In winter, pair with opaque tights for added warmth.

What to wear with brogues and oxfords

These brogues have a wedge heel and an almond toe that gives them a more feminine appearance.

What to wear with brogues and oxfords

Look for a brogue or oxford with a small heel too (these ones below are orthotic friendly as they have a removable insole – from Ziera)

What to wear with brogues and oxfords

Because of the high vamp of the brogue which can have a leg shortening effect, going for a slightly shorter skirt adds that leg length back into the proportional equation.

Wear with a Flared Midi-Skirt

What to wear with brogues and oxfords

Look for a brogue colour that isn’t really contrasting with your skin (in the way black would with my fair skin) and make sure that your skirt is flared – the contrast in shapes works well.  A high waisted midi-skirt with a tucked in top will give you the proportional ratios to assist you in creating the right balance.  The femininity of a flared skirt also balances the masculinity of a brogue.

Alternatively, a shoe in the same colour as your hair always creates a lovely bookend effect to your outfits.

More Tips on Choosing and Wearing Shoes

7 Easy Ways to Use Visual Grouping to Coordinate Colours

How to Have the Perfect Wardrobe of Shoes

Top 6 Ways to Choose Shoes to Go With Your Outfit

What Colour Shoes to Choose?

What to wear with brogues and oxfords


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  • I wear prescription orthotics and flat heeled oxfords are one of my few choices. I have them in five colors and long only for red. I have always liked the looks of flat heeled oxfords, including with knee length or shorter dresses. Think Audrey Tattou in her Doc Marten Oxfords in the movie Amalie.

  • It is so helpful to get guidelines like this with multiple real-life examples. I love shoes like this for walking, and travel but never paired them with skirts because I didn’t see ways to do it successfully. I am definitely referring back to this post when I plan my fall and winter sewing, which will include more skirts now. Yay!

  • Thank you, Imogen, for this inspiring post. The way you’ve shown them with your lovely outfits has encourage me to include at least one pair in my shoe wardrobe!!! Again, thank you.

  • Excellent ideas Imogen. I used to think of brogues and oxfords as old lady shoes until I saw your illustrated essay. Thanks, these shoes should be very comfortable for travels. The shorter skirts are especially fetching with the heavier footwear. Thanks.

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