How to Pick The Right Shoes for a Dress

You know how I always rave about dresses because they are “one-and-done” outfits and require virtually no thought. Well, that’s sort of a lie. You do need shoes. Sure, you need shoes with every outfit, but they seem to matter more with dresses because the length and style of the dress play such a big role in how a pair of shoes look on you. Dresses fall into 3 categories by length:

  1. Short (above the knee) or street length (right around the knee)
  2. Long (maxi)
  3. Mid-calf (midi)

And while these all present unique challenges when choosing shoes, the most challenging dress length to style has to be the midi. Pick the wrong shoe, and you look shorter, boxier, and yes, that dreaded word, frumpier. Pick the right one and you have a chic, wearable, and modest outfit.

For today’s video, I’m excited to be partnering with Rihoas, an elegant, affordable brand known for its French girl aesthetic and feminine dresses. I chose 4 dresses (well, one is a skirt and sweater outfit, but that counts as a two-piece dress) to illustrate how best to pair shoes with dresses.

But first, let me share some pointers.

3 Tips for Choosing The Right Shoe For a Dress

Scale

The scale (volume) of the dress should pair well with the scale (volume) of the shoe. So a sleek shoe with a fitted dress, or a chunky shoe with a voluminous dress, for example.

Flattery

A shoe with a high vamp (i.e. one that covers the whole top of the foot) is going to be less flattering than one with a low vamp. So choose ballet flats over loafers with dresses for maximum flattery. The exception? Boots. Since they go up the ankle, they continue the leg line rather than cutting it off. Straps across the ankle or at the top of the foot can also affect how flattering the shoe is. In general, the thicker and darker the strap, and the higher up on the foot, the harder it is for the shoe to be flattering.

In general:

  • High Vamp Shoes look better with pants
  • Low Vamp shoes look best with dresses (but also work with pants)
  • Booties are harder to pair with midi skirts than knee-high boots
  • A knee-high boot that extends under the skirt is a very flattering choice

Details (Functionality)

Practical considerations are another factor when choosing shoes. Are the boots to bulky to fit under the dress? Do the booties get caught in the hem and bunch up? Comfort and wearability are important considerations. For example, the boots on the left are too bulky to wear under most midi dresses, while the pair on the right are sleek enough to fit and create a nice long lean line.

Functionality can also include the shoe matching the dress in formality and in season.

Here are the Rihoas items I chose. Use code NadaM for 20% off.

And now, 4 Rihoas dresses with 6 pairs of shoes each.

The Red Ribbed Side Split A-Line Maxi Dress

To shop: https://bit.ly/3uzK3bQ. Use code Nada20 for $20% off.

Here, the pics are shown in order of the most flattering shoe to the least flattering/functional shoe.

The Black Square Neck Flare Sleeve Midi Dress

To shop: https://bit.ly/3uzK3bQ. Use code Nada20 for $20% off.

Here, the pics are shown in order of the most flattering shoe to the least flattering/functional shoe. The last shoe, while flattering, doesn’t suit the cozy vibe of the dress. It’s a summer shoe paired with a sweater dress, which makes it look off.

The Striped Two Piece Sweater Dress Set

To shop: Sweater and Skirt shown with the red cable cardigan. Use code Nada20 for $20% off.

Here, the pics are shown in order of the most flattering shoe to the least flattering/functional shoe.

The Red Square Neck Floral Velvet Midi Dress

Click here to shop this dress. Use code Nada20 for 20% off.

Here, the pics are shown in order of the most flattering shoe to the least flattering/functional shoe.

What’s your biggest takeaway from these shoe + dress pairings? Did you have an aha moment? Let me know in the comments!