Lance’s Guide to Man Grooming, Part 4: Clothing Optionals

Clothing Dept., Aisle A: Looking Underneath

Shortly after posting Part 3 of this series, I regretted making a promise that in this, Part 4, I would dive into the dangerous waters of advising anyone else about how to dress themselves. This is an area rife with landmines that are easily tripped, and in the end it comes down to you and your mirror on one side, and me and my opinions on the other.
My boyfriend, who has excellent taste (obviously) and manages on a small budget to buy precisely the right bits and pieces he can put together for nearly any occasion, from business meeting to a night out at a drag show–and I’m not talking race cars, friends–oftentimes looks aghast at my wardrobe choices. Sometimes his looks are accompanied by gasps and giggles and outright arguments.
Not without reason, I hasten to add. But that’s sort of the point; The secret to style is finding your own. That isn’t to say that everyone can’t use a little help now and again, myself included. So what we’re going to do here, you and I, is take a look in your drawers (so to speak) and sort out just what you need to create the style that is all you.

Please keep in mind that fashion is a huge, unwieldy, lengthy subject about which entire books, magazines, lifestyles and careers have been built. I’m scratching the surface, here… and I’ll still go on for thousands of words about it. I’ll certainly hand you some do’s and don’t’s before we’re finished, and I hope you’ll come away feeling better about yourself and excited about your choices. But take it all with a grain of salt and, in the end, do what you want to do.
Because you will, anyway.
The Psychology of Clothes
As you already know but I’m going to reiterate anyway for my own amusement, clothing serves two purposes; It covers us up to protect us from the elements and shield our naughty bits, and it enhances our self-esteem by making us look fashionable and stylish and attractive unless we are an underwear model working 3 hours a day on maintaining our 3% body fat and perfected six-pack ab wall in which case we’re wandering around as naked as possible all the time.
Assuming you are not an underwear model (which I think we can all agree is a fairly safe assumption) than what we all want out of the clothing we have hanging in our closets and laying in our drawers and strewn about on the floor, bed and chair awaiting folding and/or laundering is that the clothing makes us look (and therefore feel) better. To that end, there’s only a few things to look for:

  1. Does it fit?
  2. Does its color(s) and/or pattern compliment your body (shape, height, width, dimensions) and overall coloring (hair, eyes, skin and so forth)?
  3. Is it affordable?
  4. Will you actually wear it?

Simple? One would think so, but then you’re faced with moral dilemmas like:

  • “But it’s 75% off! And it almost fits!”
  • “I saw [Hot Celebrity] wearing this and he’s hot! If I wear it, I will be hot, too!”
  • “I’ve lost all that weight and now I can manage to close the waist on these pants and look! Only a couple of folds of fat are hanging over the edge! I’m thin!”
  • “I know that red makes my skin look blotchy, but I love red and I want this!”

It’s sometimes difficult to overrule the latter temptations by keeping the former rules in mind, but I urge you to do so. Look at your reflection carefully when you try something on. Are you wearing the clothes, or are the clothes wearing you? Don’t be a walking shirt. If you’re uncomfortable in it, you won’t wear it. If you feel it overwhelms you instead of complementing you, you shouldn’t wear it.
Which is not to say don’t be a little daring with your look. Men today have a lot more options and opportunity to find attractive, different, well-made, comfortable and good fitting clothes. But I think there’s a tendency to be a little bit… scared of choice. “What if I don’t look like everyone else?” “What if I stick out?” “What if this makes me look, well, queer?”
It’s easy for a guy in my shoes (Prada Sport, circa 2001, black leather and nylon with silver buckle lace catch and red stripe on the tongue) to shrug my shoulders and say, eh, so the fuck what? Isn’t that the point? You want to look like you. So it’s of utmost importance when you’re considering clothing to look at yourself in the mirror and think, “Do I like how I look in this?” Don’t think about how Brad Pitt will look in it. Brad Pitt looks good caked in shit. All that matters is how you look in it, and how comfortable you feel in it, and whether it will fit into your existing wardrobe (“Does this go with anything?”).
How to Shop
Men hate to go shopping. It’s something in our DNA. Even I, who spends way too much on shoes and shirts and outerwear, hate stepping into a grocery store. The choices are too many, I think everything’s too expensive, I regret getting things I’ll never actually use (beets? canned beets? whu huh?) and I walk out feeling like I’ve been taken.
What men like is hunting. Not necessarily in the “I really need to strap a deer on my Bronco” style of hunting, more in the basic “I have a target in mind and I will search until I locate it and claim it for myself” style. So think of shopping like hunting. You are on a shirt hunt. You are hunting for the juiciest, most satisfying shirt in the shopping wilderness, and nothing but nothing is going to stop you from that goal.
See? Shopping can be manly!
To that end, I have just a few requests to make of you when you find yourself out there in the vast, sprawling tundra of men’s clothes shopping:
1. Never say, “I like that, but I would never wear it.” I hear this a lot from guys. They see something, a shirt, a pair of shoes, a brightly-colored or amusingly-patterned tie and they will pick it up, smile, admire it, turn it this way and that, and then place it gingerly down where they found it. Clearly, they are enamored of that article of clothing, but they cannot place themselves inside it. I mean, they can’t even manage to try it on.
My advice: Try it on. Please try it on. You’re in a store, no one else will see you in that mirror in the changing room, and you might discover that it looks as good on you as it does on the hanger. Plus, just because the label says those are 34 jeans with a 32 inseam, one designer’s idea of how a man’s butt should fit doesn’t always match with another designer’s. If you don’t try them on in the store, you may find that when you get them home you’re wearing high-water pants–and high-water pants are never in style, even in a flood.
And don’t be so hasty about your fashion modeling, either. Don’t go in imagining you’re going to hate it and you just pull it on and button it up and look at yourself with the hurried demeanor of someone trying to escape a burning pink Oxford button-down. You can take your time, and also…
2. Always get a second opinion. When you go clothes shopping, you should never go alone. First, you’ll want someone to look at your backside to see what the clothing looks like where you can’t see it yourself. Second, if you don’t bring along someone you know, you end up relying on the sales clerk and, well, they might have a couple of ulterior motives regarding your purchases. I’m just saying.
To be fair, not all sales people are on commission, so to speak. Plus, if they do a good job, chances are you’ll become a repeat customer and they know that. So treat them like people instead of hired help, tell them your name and be honest with them if you’re uncomfortable in shopping situations.
3. Find a salesperson you trust. A good salesperson can be your most valued shopping asset. If you see a guy who looks like you want to look, clothing-wise, than you know his tastes approximate your own and his opinions may be more reliable for you. Obviously, if they turn out to be a total tool, ditch ’em and find someone else. But in most clothing stores, the salespeople know their product and in it’s in their best interest to make you happy.
In the event that this is a drive-by shopping experience (i.e. you saw the jacket in the window and you just had to have it!) and you need a second opinion and the sales clerk is too busy adjusting his coif or chatting up some dude in low-rise Diesels, ask a complete stranger. You heard me. Go up to another customer and say, “Excuse me, could I just ask… does my ass look fat? Seriously.” You’ll probably get an honest answer, since why should they care about offending you–and you just placed them in a trusted, stylish position. So chances are they’ll actually consider the answer before blurting out, “Oh my God, get those off your body immediately!”
Also, flirt a little if you feel like it. Why not?
4. Step outside the box. Don’t stay in the changing room, walk around a bit in your proposed new duds. Because you know what you do in your clothes? Everything. You sit in them, you walk in them, you lay on the couch in them, they have to move around and adjust to your body. Do you really want to buy those jeans you’ve only stood upright in, only to find that when you sit down they squeeze your thighs like sausages and ride up your crack so far they come out the front?
High Prices do not equal High Style
Labels came into force during the 70’s. I can remember being in High School and you could not wear a polo shirt that didn’t have a little alligator on it, and your shoes had better have a swoosh on the side or you just were not cool.
Today we’re faced with a dizzying and ever-widening array of designers and their labels and it can be enticing to believe that spending more money on a pair of jeans will necessarily mean they are of better quality, or will fit better or will last longer. Sadly, none of this is entirely true all the time.
In short, while you’re trying things on ignore everything going on except how you look in whatever you’re interested in buying. All the other considerations should be saved for later. It doesn’t matter how much that jacket will cost you if you put it on and hate it. It doesn’t matter how good the color looks with your skin tone if the sleeves end above your wrists. It doesn’t matter who made it if you look at your reflection and a smile comes unbidden to your face because, damn, you look pretty fucking seriously sexy in that thing, don’t you?
Now that you’re married to your purchase, look at the price and decide if you’re worth it. Seriously, that’s the question to ask yourself. You know you look good in it. You know you like it and will wear it. Now you know it costs about double what you were considering paying for a new (pair of jeans, dress shirt with French cuffs, casual jacket or what have you). Are you worth it? If you answer no, take them off, have no regrets, thank the sales person and move along. It isn’t like there’s not another (pair of jeans, dress shirt with French cuffs, casual jacket or what have you) to be had, right?
On the other hand, if it’s perfect, if the time is right, if you really want it (and you can afford it), buy the damned thing. There’s no more sour taste than regret.
On the other hand, if you look at yourself and think, eh, this’ll do, and the price is ridiculously affordable, think twice. What inevitably happens to me is that the “This’ll do” clothing never gets worn. Sure, I practically stole it off the rack, and it fits and it’s okay, but when I put it on I never feel the same way that I do as when I put on the “I look pretty fucking seriously sexy” clothes. So I favor the stuff I really like, naturally, and the cheap, just-okay, totally affordable nothing I bought still ends up a waste of money.
And never be talked into something you don’t like. Just because something is trendy, and simply everyone will be wearing it, and you’re told by the sales person that it’s perfect for you–if you don’t like it, you won’t wear it. Ignore trends, and start to develop your own style.
The Basics
If you’re like me, you don’t give a lot of consideration to underwear and socks. Certainly not as much to any other article of clothing you purchase, and they tend to be appetizers rather than entrees.
The style of undershorts you buy is strictly a personal preference. The notion that wearing tight-fitting undies will constrict your balls and reduce your chances of making child-producing spermatozoa has been debunked. There’s no medical reason to prefer boxers over briefs, so it comes down to how you want to look when you’re not wearing anything. Oh, and the opinion of your significant other may also factor in.
There is one thing almost everyone, male or female, straight or gay, can agree on: Boxers are not sexy. Boxers are baggy and loose and ridiculous. They may be comfortable to sleep in, but as undershorts they leave a lot to be desired. With so many choices available to you now, I urge you to look around and find something more attractive to squeeze your nice ass into. Try boxerbriefs–they’re comfortable, provide the coverage you’re looking for, have an ample basket to house your goods and come in brushed cotton which feels awfully nice against your skin.
You will also need a selection of undershirts. Always wear an undershirt beneath your dress shirt. This rule may not be broken. If you’re wearing a button-up shirt with long sleeves and a collar, accompany it with an undershirt, preferably a white one. I am also of the school that believes V-neck undershirts are a product of Satan. Crewneck only, gentlemen.
Undershirt fit is very important. Guys tend to buy their undershirts one size too large. This is acceptable when buying T-shirts (for purposes of our discussion, I’ll refer to undecorated, generally white, 100% cotton T-shirts as undershirts, and T-shirts you wear unaccompanied by another shirt and sometimes decorated and usually not white as T-shirts) but the purpose of an undershirt, as the name implies, is that it is to be worn under another shirt. Therefore, in order for your dress shirt to drape nicely, your undershirt should interfere as little as possible with your shirt. Not necessarily tight, per se, but the goal is to have an undershirt with as few wrinkles as possible.
Contrary to what you may be thinking, undershirts do not only come in S, M, L and XL. Undershirts also come tall (longer body) or fitted (tapered body). Understanding the type of body you possess will help you get a better fitting shirt.
A few rules of thumb:

  • You should be buying new underwear (undershorts and undershirts) at least twice a year.
  • Throw the old ones out. Do not give them to Goodwill, no one wants them–not even you.
  • You should have at least as many pairs of underwear as there are days of the week.
  • You should change your underwear daily.
  • Have at least one pair of sexy underwear.¹

How much should you spend on underwear? Me, I buy my undershirts from Gap. They come in tall or fitted or stretch (which I guess could be thought of as super-fitted) and you can get them in white, light or dark gray and black. They often have sales so you can stock up and keep rotating your undershirts so you’ll always look fresh, crisp and clean. I would like to steer you away from buying ‘bulk’ undershirts where you get half-a-dozen wrapped tight in a vacuum-packed plastic bag. They’re of shoddy, thin material, will get stretched out of shape too easily and won’t last long at all.
Undershorts are a little bit trickier. If you wear jeans, mostly, you’ll want to get undershorts that fit your body well, so your ass doesn’t squeeze over or under the seat, your cock and balls are nicely supported and overall they are neither too loose nor too tight. Unfortunately (or fortunately) you aren’t normally allowed to try on underwear in the store.
However, if you’re not buying tighty-whiteys and you’re going for more coverage from square-cut or boxer-briefs, you’ll generally have less problems with fit simply because there’s more material to go around. On the other hand, I’ve tried on some pairs (namely Calvin Klein) and the leggings ride up uncomfortably because there’s not enough there for my thick, muscular thighs (or so I tell myself). So, again, buy some, try some, find a brand you like and stick with it.
1. Everyone needs sexy underwear. If you think this is the sole province of the ladies, you’re oh so wrong. Get over yourself and revel in your sensuality and sexy body. If you’re embarrassed about sliding your purchase across the counter and under the judging eyes of the sales person, buy it online. Be sure to bring your lover in on the decision-making. And splurge, baby. You’re worth it. (And, no, it doesn’t make you gay. Ask your girlfriend if she’d like to see you in something besides the same old ratty shorts. My guess is she’ll be out buying them for you before you’ve finished asking.)
What can one say about socks, really? Other than, “If you’re wearing shoes, you should be wearing socks.” I am 100% against the sockless look once championed by the questionable talents of the cast of Miami Vice, and currently promoted by the so-called fashion expert on Queer Eye, whose opinions I often agree with but tend to think he dresses a bit too much like a circus attraction. And don’t get me started on wearing a tie as a belt!
But we’re not even there yet, we’re staring at your feet.
Socks aren’t the most glamorous of clothing articles, and are usually more about utility than fashion. There’s no doubt that you can find socks in as many different colors, patterns and styles as pretty much every other piece of a man’s wardrobe, and frankly if you can’t bring yourself to add some color to any other part of your body, hiding up your pant leg (you should excuse the expression) is a fine place to start.
When I was but a lowly bank employee, we had to wear decidedly boring clothes; navy blue or black suits, white or blue shirts, black or brown shiny leather shoes. There were only two places we were allowed to be what could be considered creative with our ensemble; ties and socks. Most guys, they wore black socks. Some wore knee-length, some wore mid-calf, some wore what were in essence black athletic socks. I elected to take a different path.
My socks were uniformly garish. Not just colorful, friends, these were socks akin to bad acid trips or something that might occur if a Scotsman threw up after a night of eating oriental rugs and bottles of Pepto Bismal. Paisley nightmares of intrusive hues like fuchsia and lime and tangerine. Plaid creations from a Tolkien fever dream. Floral prints, stripes, polka dots–if it was loud and colorful and downright offensive in its need to show off, I owned them.
Of course, a lot of the reasoning behind my desire (at that time) for loud socks was two-fold. First, it was my own silent revolution against The Man. No corporate structure, even an implied one, was going to tell me how to dress, at least not entirely? You want me to blend in? Fine, but guess what I have up my pant leg!
Secondly, hello! Closeted fag, here! Maybe it’s in my DNA or something, but I just had to have some color somewhere. It was suffocating otherwise.
When I sat in meetings and crossed my legs, the pant leg would raise and uncover my latest find. And do you know who loved my socks? The women. The women loved me and loved my socks. They would demand that I stand before meetings and unveil what was under my pants, gentlemen. They would coo and swoon and point and smile and nod. These banking women, also confined in vestments of dark wool and ugly, ugly shoes, knew the value of style no matter where you find it.
I managed to get away with a few interesting ties, as well, but I never wanted my tie to outclass me, if you get my meaning. I didn’t mind being “the socks guy,” because it was like having a great, happy secret. A loud tie says to some people, “I got this for Christmas and I know it doesn’t actually go with what I’m wearing, but I only own three ties and I’m a very messy eater.” Loud socks, if you can carry them off, add a dash of panache to an otherwise unassuming demeanor. They say there’s something else going on with you, something special and hidden… and people will want to find out what that is.
At least, that was my experience.
Currently, I favor two colors of socks: Black and white. I also own a few pairs of racy, daring, interesting stretch hosiery I bought at Barney’s and Sak’s, but those are for special occasions. I no longer need shocking socks, because I’ve usually got color coming off me in deep waves so there’s little need to hide my more colorful side within my shoes. Black and white socks go with everything, I have found, and usually I want people staring at my ultra-cool shoes rather than my somewhat dreary but very functional socks.
Again, I buy my socks at Gap. I’m buying them as disposable parts of my wardrobe so I don’t spend a lot on them. I want them to stay up and not sag down my leg so I have to constantly tug at them, and the Gap socks have some good elastic in them.
So here’s some advice for you. If you’re looking for someplace unobtrusive wherein you can start to display your more adventurous, interesting, and stylish side, start with your socks. It’s a relatively inexpensive investment so if you find you hate them, you’re not out a lot of dough if you feel like you can’t bring them off. You can find an endless array of styles and colors to choose from. They’ll always fit. And you can fill up a sock drawer with socks and no one will arch a brow and call you a clotheshorse.
You’ll just be a guy with a lot of socks.
Still to come: Shoes, Pants, Shirts, One Perfect Suit, Things You Should Never Wear and the Successful Accessorizer.

July 2, 2004

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