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What Shoes to Wear? Tips for Stylish, Warm, and Comfy Choices

By Imogenl @ImogenLamport
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I hear you when you say that picking shoes to wear with your outfits can be tricky—especially when you just want to keep your feet warm and comfy in the cooler months! Here’s a guide to help you select the best shoes based on your outfit, body proportions, and comfort needs.

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1. Level of Refinement

One key factor to consider is the level of refinement. This refers to how casual or dressy your shoes and clothes are. Your shoes should generally match the level of refinement of your outfit:

  • Casual shoes (like sports sneakers) work best with very casual outfits.
  • More refined shoes (like dress sneakers or leather flats) are better with smarter, casual looks but aren’t too formal.  Sneakers will always dress down an outfit, even if they are a dress sneaker rather than a running shoe.  This is because they come from a lower level of refinement.  A ballet flat or flat boot (ankle or knee high) will always dress up an outfit more than a pair of sneakers.
  • Heels and dressy flats work well with more refined or dressy outfits.  Think refined ballet flats, kitten heels,  and even wedges.

Think about how your shoes fit with the overall tone of your outfit. Are you aiming for casual comfort or a more polished, put-together look?

2. Body Proportions and Shoe Vamps

The vamp of a shoe (how high it comes up on your foot) plays a big role in how it affects the length of your legs:

  • Low vamp shoes (like ballet flats or pumps) elongate the legs, making them appear longer. These are great with skirts and dresses, especially if you have shorter legs.
  • High vamp shoes (like ankle boots or brogues) can visually cut the length of your legs, so they work better with trousers, maxi skirts or short skirts where either the leg is completely covered or more leg is showing.

If you have long legs, you can get away with high vamp shoes with skirts or dresses  If you have shorter legs, opt for low vamp shoes or nude shoes that blend with your skin tone to avoid breaking up your leg line when wearing skirts or dresses that have hems on the knee or below.sneakers can work with a maxi skirt

Sneakers can work with a denim maxi skirt (like I’m wearing here) as there is length through the garment, ideally match the colour of your sneakers to the skirt if you have shorter legs, or to  your hair if you have long legs like me!

3. Shoe Scale and Outfit Scale

The scale of your shoes should also match the scale of your outfit and your own personal scale. For example:

  • Chunkier shoes work well with outfits that have more volume, like wide-leg pants or flared skirts.
  • Sleeker shoes are better suited for more fitted or refined outfits like pencil skirts or skinny trousers.

dress sneakers always make a look more casual

Here I’m wearing a metallic wedge dress sneaker, the metallic finish makes the look a little more polished, but the rubber sole of the sneaker always dresses down a look.  The wedge works to balance the volume of these wide leg trousers.

Also, consider the size of your feet and ankles. If you have smaller feet, oversized chunky shoes can look unbalanced. Similarly, more delicate shoes might look too small if you’re wearing bulkier clothes.  If you are petite, a chunky shoe will look out of balance with you as a whole.

4. Staying Warm and Comfortable

If warmth and comfort are priorities, here are some stylish options:

  • Knee-high boots are fantastic with skirts and dresses in cooler weather. Even though they go up to your knee, they act like low vamp shoes by elongating the leg line, creating a seamless look.
  • Ankle boots work best with trousers or jeans, especially if they’re slim or cropped at the ankle.
  • Ballet flats are a great option for skirts and dresses if you’re after comfort, while still wanting a low vamp style that flatters your leg line.ankle boots dress up jeans

Ankle boots are great with trousers and jeans and they give a more dressy appearance than sneakers. I painted these ones from beige (which were great when I had blonde hair) to silver to match my natural hair colour.

5. Practical Tips

  • If you have shorter legs and love wearing skirts or dresses with boots, go for nude knee-high boots to elongate the leg line.
  • Avoid wearing ankle boots with skirts or dresses if you have shorter legs, as they cut off the leg line at an awkward place.
  • For casual pants, sneakers or ankle boots are great, but if you’re looking for something that works across styles, a more refined flat (like a leather ballet flat or loafers) can offer both comfort and versatility.

Final Thoughts

Shoe choices are about more than just comfort—they can elevate or detract from your entire outfit. By considering factors like refinement, body proportions, and scale, you can make more informed choices that not only feel good but look great too. So, whether you’re reaching for your comfiest flats or styling boots with a skirt, these tips will help you feel confident that your shoes are the perfect finishing touch.

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What Shoes to Wear? Tips for Stylish, Warm, and Comfy Choices

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What Shoes to Wear? Tips for Stylish, Warm, and Comfy Choices

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