Entertainment Fashion & Style Men's Shoe Rules to Live By 23 Footwear Tips That Will Keep You Looking Good Share PINTEREST Email Print rolandvaneck/Getty Images Fashion & Style Shoes Accessories Tops & Sweaters Dresses Skirts Jeans Pants Do It Yourself Skincare Advice Makeup Hair Fragrance Tattoos and Body Piercings Kids and Teens Bumps & Babies Learn More By Craig Playstead Updated on 02/13/18 What are the shoe style rules that men need to follow to be sure they look great and they are wearing the appropriate footwear? Here are the guidelines that can give you confidence in what you're wearing on your feet. Color Rules for Shoes, Socks, and Belt Your shoes should be darker than your pants. The darker your suit, the darker your shoes. This simple rule will keep your choice appropriate for formal, business, and casual outfits. Get a pair or two of black shoes, they will go with any choice but navy pants, in which case you need dark brown or black Bordeaux (reddish-brown). You can wear brown shoes with brown pants, but they should be darker than the pants. Match your socks to your shoes. They should be a nice bridge between your shoes and your pants rather than a contrasting color. Your shoes should match your belt. Don't pair a brown belt with black shoes or vice versa. Best Shoe Styles When in doubt go conservative over edgy. You don't want to spend good money buy shoes that will look dated in just a few months. Loafers go with just about anything. Wingtips are cool again. Buy a nice pair of brown oxfords, they go with almost anything. Make sure you have one great pair of boots. Shoe Buying Rules Always choose fit over style. You won't look great if your feet hurt.When in doubt go conservative over edgy. You don't want to spend good money buy shoes that will look dated in just a few months.Your shoes should be the most expensive part of your wardrobe. Always spend money on shoes rather than shirts or pantsSplurge once a year on that pair of shoes you really want. Sandal Rules No socks with sandals. Buy new flip-flops each summer. No flip-flops at work. Unless you work at a surf shop. Don't wear sandals if you have gross feet. Boot Rule Cowboy boots don't work with suits. Unless you are a real, honest to God cowboy. Sneakers and Athletic Shoe Rules Be careful when wearing sneakers with khakis, you run the risk of looking older than you are. Be fitted for running shoes if you're going to push yourself. You need to know you are getting the right mechanics for overpronation, support, and cushioning. Go to the most serious running shoe store in your area to get properly fitted by experts who care about your running. Replace your workout shoes at least every six months. Try out the new athletic shoe trends before training with them. Walk around in them in the house and take them out only for short runs at first. Buy them at a serious running shoe store that has a generous try-out and returns policy. Shoe Appearance Rules Your dress shoes should always be shined and looking good. Know how to shine your shoes, and if you can't do it, find a professional shoe shiner. You'll get great looking shoes and an interesting conversation.