How to Wear High Heels (for Men)
If you've never worn heels before, look for shoes that have low, thick heels so you can get used to how they feel. For something more fashionable, pick up a pair of stilettos with tall, thin heels. When you're ready to rock your heels, turn your feet out slightly and walk forward on the balls of your feet, remembering to keep your chest up, abs tight, and knees relaxed.
Choose elevator shoes or shoe lifts for an invisible boost of height. If you want to look taller without the obvious addition of heels, elevator shoes are the choice for you. They look like regular dress shoes, but contain an extra insert inside, either attached to the shoe or removable, that can add anywhere from 1-6 in (2.5-15.2 cm) of height. You can buy the inserts, known as shoe lifts, separately. Place them in any dress shoe or lace-up boot for a few extra inches of height. Go with low-heeled boots for a subtle, trendy look. Another low-key way to boost your height, low-heeled men's boots are clomping their way back into fashion. You can buy them in leather or suede varieties for a retro or classy feel. Don't be afraid to take a look at women's boots too! Some of them look more masculine while others look more feminine. If you choose women's boots, be aware that they might be more narrow than you're used to. Consider a pair that's labeled "wide." It'll be more comfortable. Wear low heels or wedges to feel fashionable but comfortable. If the high heeled look is what you're after, start out with lower or thicker heels. Look for heels that are an inch-high or smaller, with a thick heel or even a platform sole. These platforms are known as wedges, which refers to the solid block, or “wedge,” that runs from heel to toe and supports the foot while adding height. A low-heeled boot can also be a great way to ease into wearing higher heels, for your own physical comfort as well as subtlety. If this is your first time wearing heels, choose lower heels or wedges for your first pair. The next set of heels can be the height you want, such as sky-high stilettos. Go with stilettos if you’re feeling confident and experienced. Stilettos have the classic thin, high, tapered heels. They're gorgeous, but notoriously difficult to walk in! If you've walked in lower heels before and feel up to the challenge, buy a pair and try them out. Don't give up if you can't manage the height. Keep practicing, and you'll be rocking them in no time. Figure out your size in women’s shoes. If you think you'd feel a bit uncomfortable having store employees size you up for women's shoes, or simply want to save time in the store or online, knowing your size in women's shoe's can streamline the whole process. In the US, women's shoes are about 1.5-2 sizes smaller than men's. For example, if you wear a size 10, you'll wear either an 11.5 or 12 in women's shoes, including heels. Go to a department store if you have smaller feet. Most department stores don't carry women's shoes, including heels, in sizes larger than a US 10. If your feet are smaller than about an 8 in US men's, browse the shoe department of your local department store. With the large selections of heels at department stores, you're bound to find something you'll like. If you feel comfortable, ask a store employee to help size you and recommend shoes. Try them on in the store for size and comfort. Try on your heels in the store if you feel comfortable. It's OK to feel a little uncomfortable or awkward on your first trip to buy heels. If you'd rather not try your heels on in the store, you can simply estimate your size and ask an employee to bring you a pair without trying them on. You can give them a test run at home and return them later if they don't fit. Say they're for a family member or friend if you want to avoid questions. There's nothing wrong with taking pride in your heels, since you already know you'll look great in them! On the flip side, there's also nothing wrong with keeping it to yourself if that makes you more comfortable. Order from an online or specialty store if you have larger feet. If you want a larger selection or more size options, or you simply want to avoid a trip to the store, head to an online vendor. You'll find options for larger-sized women's shoes as well as shops that sell heels made specifically for men, wider and longer than the typical women's heel. Some stores even offer a custom-made service if you know exactly what heel you want but haven't found it in stores. Test your heels’ stability with the “rocking technique. ” In the store or right after you receive your heels at home, stand them on a table with the heels facing you. Give the heels a couple good taps. If they rock side to side, they're not stable and will be difficult to walk in, so consider returning them for a new pair. If the second pair rocks as well, there might be something wrong with the design itself. In this case, you might have to choose a different style of shoe. Try on your heels to test the fit. Make sure that your toes aren't pressed too tightly in the toe box, which could be uncomfortable and cause blisters. The toe area shouldn't be too loose, either, or you'll walk right out of the shoe. Closed-heel or closed-toe shoes should have some wiggle room in the heel counter (the back of the shoe where your heel slips in), but not so much that your foot slides out while walking. For an open-heel or slingback shoe, ensure that your heel touches the back of the shoe without creating a gap or hanging off of it. Stretch your feet with warm-up exercises. Stretch out your toes and spread them wide, then rotate your ankles in small circles to the left and right. Point your feet and toes straight, then flex them so the toes are pointing straight into the air. A few easy exercises will loosen and strengthen the muscles that will be working when you walk in your heels. Sit down and slip on your heels. Take off your socks and strap your shoes onto your bare feet, or wear nylon stockings or pantyhose to help with a smoother fit. Some shoes will have a small strap with a buckle while others will simply be slip-on, so make sure to look at your shoes carefully before pulling them on. Stand up straight and find your balance. Focus on having good posture and keeping your spine straight, which will help with your balance. It might feel strange at first to have most of your weight thrust forward onto your toes. Don't worry; wearing heels for the first time is weird for everyone, men and women alike! Relax and let yourself get used to the weight shift. Take a few small steps, relaxing your knees and hips. Allow your knees to bend as you walk and turn out your feet slightly so your inner thighs are turning towards the front. Set the ball of your foot down first so that it touches the ground just before your heel. Let your hips relax and move naturally. Think about being flowing and graceful with your limbs and movements while keep your back straight. Keep your chest up and your lower abs tight. Pulling back your shoulders and keeping your chest high will help to counterbalance the weight shift onto the balls of your feet. Engaging your lower abs will help to stabilize your lower back. As a bonus, good posture will also help you feel confident in your new heels. Place one foot in front of the other as you walk. This will help your hips roll naturally and prevent you from walking bow-legged. Remember not to cross your legs too dramatically as you step, though; that will throw you off balance, and look a bit strange! Simply focus on putting one foot right in front of the other. Practice your walk in front of a mirror a few times. Keep an eye out for a few common mistakes of walking in heels, such as letting your ankles wobble from side to side or keeping your knees stiff, which will cause you to lean forward and have bad posture. You might also see that you're leaning back too far as you walk, which means that you're keeping your thighs too tense. Remember to stand straight with your shoulders back and stay relaxed through your hips and knees. Alternatively, film yourself walking, then watch the recording. Note any mistakes, such as wobbly ankles or stiff knees. Practice walking in your heels whenever you can. Have fun with it! Pretend that your hallway is a catwalk and strut your stuff. The more you practice, the more comfortable your heels will feel--and the more confident you'll feel while wearing them. Wear slacks and a regular shirt with elevator shoes. The point of elevator shoes is to provide an invisible boost of height, so there's no need to draw particular attention to them. Simply dress like you normally would with a pair of nice shoes or boots and enjoy the extra few inches. Pair low-heeled boots with dark wash jeans. Short boots are great for a rock-and-roll look, especially when paired with fitted jeans and a low-key shirt. The slim jeans will call attention to the boots without seeming over-the-top. Wear tight jeans, leggings or capris to show off higher heels. Throw on a t-shirt for a more casual look, or wear your heels with a full fitted suit. Heels with tight pants accentuate your legs in the best way. Choose a dress or skirt for a trendy, gender-bending look. Male celebrities have started to rock dresses on social media, while fashion designers often dress male models in skirts with heels. Men wearing skirts is definitely the new fashionable trend, so try it out for yourself! Pair your heels with a knee-length dress or skirt. Look for a color that matches your heels. Nude heels can go with pretty much anything, while black heels look best with black dresses. Continue wearing your heels in private if you feel like it. It's fine if you'd rather not debut your heels in public just yet, or maybe ever. Do whatever makes you comfortable and happy, whether that's rocking your heels on the street or simply in the privacy of your own home. Walk around in a safe, uncrowded area to build up your confidence. If you feel a bit nervous about walking outside in your heels for the first time, start small. Walk around in a park where you feel safe and comfortable. Remember to stand up straight with your shoulders back; assuming a strong posture will help you feel confident and poised. Walk with a friend and chat as you go to keep yourself relaxed. They can give you tips, help calm you down if you feel nervous, and catch you if you stumble. Walk on the streets if you’re feeling comfortable and confident. When you're ready, wear your heels in more normal streets and busier areas. Keep an eye out for any bumps, cracks or grates in the sidewalk. If you're still feeling shy or nervous, remember that most people won't even look at you long enough to notice your shoes. Act normally and walk confidently; by now you'll be a pro at walking in heels! If you get harassed by someone, ignore it and keep walking. If they see that their words don't stop you from rocking your heels, they'll probably give up. If they keep pursuing you, duck into a crowded store or turn a corner. If all else fails, call the police. No matter what happens or what anyone says, don't let bullies or a bad experience ruin your confidence. 
Choose elevator shoes or shoe lifts for an invisible boost of height. Go with low-heeled boots for a subtle, trendy look. Wear low heels or wedges to feel fashionable but comfortable. Go with stilettos if you’re feeling confident and experienced. Figure out your size in women’s shoes. Go to a department store if you have smaller feet. Try on your heels in the store if you feel comfortable. Order from an online or specialty store if you have larger feet. Test your heels’ stability with the “rocking technique. Try on your heels to test the fit. Stretch your feet with warm-up exercises. Sit down and slip on your heels. Stand up straight and find your balance. Take a few small steps, relaxing your knees and hips. Keep your chest up and your lower abs tight. Place one foot in front of the other as you walk. Practice your walk in front of a mirror a few times. Practice walking in your heels whenever you can. Wear slacks and a regular shirt with elevator shoes. Pair low-heeled boots with dark wash jeans. Wear tight jeans, leggings or capris to show off higher heels. Choose a dress or skirt for a trendy, gender-bending look. Continue wearing your heels in private if you feel like it. Walk around in a safe, uncrowded area to build up your confidence. Walk on the streets if you’re feeling comfortable and confident. 