Column 7:

The Young Man’s Guide to Wearing and Shopping for Women’s Clothes for the First Time

1. Decide on the store where you will be shopping. The best ones are either large, second-hand thrift stores like Buffalo Exchange, or mid-range mall department stores like Old Navy. Someplace where the employees will be too bored, high, or pretentious to bother you by offering assistance. Avoid higher-end places even if you can afford them; they’re too small and their employees are too annoyingly helpful for any reasonable sense of anonymity. Conversely, avoid bargain basement boutiques even if you’re dirt poor and have to save up even for the thrift store, as you will perish under a stampede of price-savvy single moms while you fatally pause, attempting to figure out if you’re a size 16 or a size 18.

2. Arrive outside the store. Casually peer inside. Walk around the block and/or mall floor. Rub your arms nervously. Repeat a few times. This will build your confidence.

3. Go home. Particularly if you are in a mall, any security guard watching you will think you are casing the joint, and not only that, doing an awful job of it. Dig through the cupboard for some noodles and a jar of Prego Alfredo sauce. Lift the jar up and put it back down. Decide you will never fit into the clothes you desire with habits like these. Take out some whiskey instead. Pour a double shot into a tall glass with some Diet Coke. Have a few of these. Convince yourself you probably never really wanted women’s clothes anyway. Maybe it was just a phase. Stagger into your roommate’s bedroom and challenge him to wrestle. Lose. Go to bed.

4. Wake up in the late morning with renewed determination. Go to the store immediately. Discover an intense hunger en route. Get a burger.

5. Arrive again in front of the store entrance. Pop half a Xanax. What the hell, pop another. Glide into the store on a cloud.

6. Look at the skirts section. There will be women there who appear at ease, or at least they will to you. Feel a rather bloated maleness. Finger the last Xanax in your pocket.

7. Go to the women’s pants section. Decide this will be a way to ease into this mysterious part of the store. Try to figure out your size. Remember that sizes on women’s clothing seem to follow no rooted system of measurement. Grab a bunch of different sizes of jeans, as well as a pair of Dickies. Scurry into the dressing room.

8. Find that none of the pants fit except for the biggest size. (The Dickies in particular give your legs and belly the appearance of a smokestack belching out a melted gumball.) Look at yourself in the mirror. Decide that even the pants that fit look terrible. Go back into the store. The skirts section will now look appropriately inviting.

WARNING: Do not under any circumstances go to the dress section. Do not look at the dress section. Do not think about dresses. Men gather fat in their belly, women in their butt and thighs, therefore, skirts will probably be the easiest for you to pull off. There’s also the broad shoulder factor. So stop looking at the fucking dresses, unless one of the following three apply: a) You are tiny of frame and weight (in which case Step 8 may not apply to you, also, you are an asshole.) b) You are rich in self-esteem. c) You have a lot more Xanax in your pocket.

9. Stride over to the skirts section. Be bold. Hold your head up. Summon some classic male entitlement. You are a Paying Customer. See a clerk’s head tilted slightly, looking at you. Feel your throat close up. Say “Huuurk!” Retreat to the men’s pants section. Feel simultaneously comforted and bored by the sizes that follow a comprehensible system of measurement.

10. Leave the store. Take the last Xanax.

11. Devise short yet complex stories in case someone asks you why you’re trying on women’s clothes. Enjoy this step. Be creative. “My girlfriend and I are the same size, and I want to get her something nice,” or maybe, “Well I’m a clothing designer, actually, and I think men need to really feel the clothes if they’re going to design them to be worn. This is part of my job, actually.”

12. Weigh the ludicrousness of these statements. Sigh. Go back into the store and check out some skirts. Don’t look up. Concentrate intensely. Hope fellow patrons think you are a store employee examining merchandise. Attain a deep seriousness. Discover you have terrible gas. Regret that burger even more than you already have.

13. Find something you think is nice. A brown, soft cotton knee-length thing that will drape in a flowing, subtle manner on your body, maybe, swishing around over a pair of tights, perfect on a cool fall day. Or something white, made out of impossibly thin fabric, with bright green flowers and green lines running along the sides, narrow at the top and widening to the bottom just below the knee, like something you might have seen a girl wear to the park in high school, sitting cross-legged and laughing with the skirt barely draping her knees, while you sat in huge jeans that seemed to billow around your legs, perspiring in a thin sweatshirt (you’ve never liked showing your bare limbs) feeling, again, that clumsy bloated-ness. Watching the skirt’s thin white zipper sway by her right hip as the lower inch of the skirt flutters in a light breeze, looking with a confused, implacable desire that only much later did you recognize as envy.

14. Anyway, find something like that. Take it to the registers. Pick up a pair of black socks on the way. You will not be sure why, but it will make you feel better. Try to pick the cashier that seems most disinterested in her general surroundings. Ask rapidly if you can have a bag. Find the bag is already clutched in your hands. Run out.

15. Go home. Take the Alfredo sauce out of the cupboard. Boil some water. Find your roommate playing video games. When he asks what you were out doing, laugh with exaggerated hysteria and tell him you were nailing chicks. Such banter is unusual for you. If your roommate comments on this, inform him that he is a fag.

16. Lock yourself in your room. Strip down to your underwear. Look at your blue plaid boxers. Every young man in America seems to own boxers just like these. Take them off too. Look at the skirt. Catch a glimpse of your body in the mirror. It looks dirty. Go take a shower. Wash every part of your body carefully. Decide to shave your armpits for the first time. When you’re done, do your legs too. Get up to the top half of your thighs before the hot water runs out. Discover a small amount of cuts and rashes when you towel off. But other then that, enjoy the smoothness. Don’t look in the mirror. It’s not helpful. Depending on how strongly you feel about this whole thing, it very well may not be helpful for a long time. Run your hands up and down your legs in the still-steamy room.

16a. Your roommate may inquire, “The fuck are you doing in there, watching Lord of the Rings? I’m about to take a shit in your closet!” while pounding on the bathroom door. If this is the case, remind him of the fact that he is a fag.

17. Get back into your room. Without underwear, step into the skirt. Slide it up your legs and zip up the side. Walk around. Let yourself even twirl, perhaps. Fall back on the bed. Get up again. Sit down cross-legged. Admire the spot where the skirt meets your shaven knee. Think about going out like this. Be afraid. Put your head in your hands.

18. Hear your roommate knock on your door. “Hey man? I ate your noodles and your Alfredo sauce. I’m sorry. I was hungry. We can go for burritos if you want. My treat.”

19. Open the door. See his eyebrows bounce in surprise. Tell him, “That sounds great. I gotta change though.” See him nod. Come back out in a T-shirt and jeans. Hear him say, “You’ve seemed kinda shaken up the last couple days.” Nod. Say, “I think I need to see somebody. There’s something I need some help about.” See him nod back.

20. Get to the burrito place. Order. Think about underwear. Think about those stupid boxers. Wonder if you could try on one of your friends’ bras to figure out your size. Ponder if you have the guts to do that. Decide you can probably at least buy some underwear. You can do that. Receive your burrito. It smells delicious.