What Shoes to Wear With What: A Stylist's Simple Guide
"Which shoes do I wear with this?" is one of the questions I get asked most. It makes sense. The right shoes can make an outfit look finished, and the wrong ones can make a great outfit feel slightly off without you knowing why.
The good news is that it mostly comes down to a few simple principles. Here's how to choose, outfit by outfit.
The three things that decide which shoe works
Proportion. Shoes change where the eye stops. A shoe that continues the line of your trousers or legs makes you look longer. A shoe that cuts across it, like a chunky ankle strap or a boot that stops at the widest part of your calf, shortens the line. That isn't always wrong, but it should be a choice.
Colour. Matching your shoes to your trousers, tights or skin tone creates one long, unbroken line. A contrasting shoe draws attention to your feet. Your personal palette helps here too: shoes in one of your season's neutrals will go with far more of your wardrobe than shoes that fight your colours.
Style personality. The same outfit feels completely different with loafers, trainers or heeled boots. Choose the shoe that says what you want the outfit to say, whether that's relaxed, polished or playful.
What shoes to wear with wide-leg trousers
Wide-leg trousers look best when the hem nearly skims the floor, so choose your shoes before you get them hemmed. Shoes with a little height or a pointed toe peeking out keep the look balanced. Good options are block-heeled boots, loafers with a slightly chunky sole, platform trainers or pointed flats. Very delicate, flat shoes can get lost under all that fabric.
What shoes to wear with straight-leg jeans
Straight-leg jeans are the most flexible of all. Loafers, clean trainers, ballet flats and ankle boots all work. With ankle boots, the hem should sit on top of the boot or just above it, rather than bunching over it.
What shoes to wear with cropped trousers
Cropped trousers are designed to show a bit of ankle, so pick shoes that leave it visible. Loafers, low trainers, mules and slingbacks all work well. High-cut boots tend to hide the gap that makes cropped trousers look intentional.
What shoes to wear with a midi dress or skirt
Midi lengths can feel tricky because they end mid-calf. The easiest options are:
Boots that disappear under the hem, so there's no gap of skin between skirt and boot.
Knee-high boots, for a sleek, continuous line.
Low-cut shoes, like ballet flats, mary janes or simple sandals, which show more of your leg and keep things light.
Chunky ankle boots with a visible gap can work too, especially for a more casual look, but they shorten the leg the most.
What shoes to wear with a maxi dress
Keep it simple. Flat sandals, clean trainers or a platform sole all suit maxi dresses. A little height helps if the dress is long enough to trip over.
What shoes to wear with a mini skirt or dress
Knee-high boots, loafers (with or without socks) and chunky trainers all balance a short hemline. For a more polished look, try a slim ankle boot in the same colour as your tights.
What shoes to wear with tailored trousers and suits
Loafers, derby shoes, pointed flats, heels and minimalist leather trainers all work with tailoring. The more relaxed the shoe, the more modern and casual the suit will feel. This works for everyone, whatever you wear to work.
Amsterdam-proof shoe tips
Styling advice has to survive real life, and in Amsterdam that means cobblestones, cycling and rain.
Choose block heels over stilettos. They're steadier on cobblestones and easier on the bike.
Look for grippy soles. Wet tram tracks and bridges are slippery.
Invest in one good waterproof boot in one of your neutrals. It will do more work than almost anything else in your wardrobe.
The shortcut: know your framework
Most "which shoes?" questions get much easier once you know your colours, your body's proportions and your style personality. That's exactly what we work out together in a Complete Style Assessment. If your wardrobe is full of outfits that never quite feel finished, a Wardrobe Edit & Outfit Restyle is where we put it all into practice, shoes included.