I always end up with a closet full of shoes but I never know which ones to wear. Sometimes I think I've wasted money because then I can't match them with anything. What are the really versatile styles that are worth having?
The trick is to start with what you actually wear, not what you think you should have. If you notice certain shoes sitting at the bottom of your closet, they probably don't match your real lifestyle. Rather than filling up on shoes for occasions that happen once a year, it's better to invest in a few styles you wear often and that work with most of your clothes.
Neutrals definitely help, but comfort and context are even more important. If your day is spent between home and quick errands, a white or gray sneaker will save you. If your everyday life is more formal, go for a loafer or a flat in black or taupe. Add just one shoe for special occasions, like a pump or an elegant sandal, and you're set. As for the rest of the shoes you don't wear at least twice a month? Consider letting them go.
The most important thing is to start with neutral colors - black, white, beige, gray - because they'll go with everything you already own and you won't have to think twice about it in the morning. Get yourself a pair of classic sneakers (like white or black ones), a pair of loafers or ballet flats, and maybe a versatile ankle boot, and you've already covered most situations from around the house to work to casual dinner. Avoid buying models that are too trendy or colorful if you don't already have a wardrobe built around those tones, because you'll end up in that exact situation where you have gorgeous shoes but can't find anything to wear with them. If you want to be honest with yourself, before buying a shoe ask whether it matches at least three outfits you actually wear.
If your problem is that you have shoes you don't wear, you're probably buying for hypothetical occasions instead of what you actually put on. The right move is to start from what you actually do: how many times a week do you leave the house? Do you work in an office, from home, on the go? Do you go out in the evenings often? Once you know how your time is spent, pick styles that cover those recurring situations, not the exceptions. For example, I realized I was buying fancy shoes I never wore, while I was going around in comfortable shoes every day. So I cleared out half my closet and invested in pairs I actually wear.
For real versatility, it's worth having a boot or mid-height shoe that sits between casual and formal - like a Chelsea boot or an ankle boot, that you can wear with both jeans and a dress. Then a decent sneaker (not for sports, but for real urban walking around), and if your job or life requires it, something more formal. Neutral colors help, sure, but the most important factor is that they're comfortable: a beautiful shoe you suffer in, you won't wear it, period.
The other thing I'd suggest is being honest before you buy: can you see yourself wearing this shoe next week? If the answer isn't an immediate "yes," it's not for you. Better to have five pairs you wear regularly than twenty sitting in your shoe rack.
What nobody tells you is that the real problem isn't choosing the right shoes, but stopping yourself from buying those "perfect for the occasion" ones that never actually come up. Like, how many times do you actually find yourself wearing stilettos or hiking boots? I only figured it out when I actually cleaned out my closet and realized I wear the same three styles all the time. Before you buy anything else, pull everything out and look honestly at what you actually wear and what you don't. If a shoe's been sitting there for six months, it's not a coincidence - it just doesn't fit your real life.
The thing maybe others glossed over is this: neutral colors aren't enough if the shoe isn't comfortable or doesn't match how you actually move. A beautiful gray sneaker is pointless if you hate sneakers. Better to have fewer pairs that you actually wear than a closet full of "versatile" stuff you never touch. Think about your typical days - work, going out, home - and buy shoes that work for those. If you're always in jeans and t-shirts, a nice pair of black loafers or ankle boots is more useful than expensive dress shoes you'll wear once a year.
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