All Request Day: What Is A Well-Dressed Man? Part 1.

An exasperated commenter requests a post:

Just what the hell does it mean when women say that they want a well dressed guy? What does well dressed mean for a guy?

A wonderful question.   In my experience, there are three general categories of men when it comes to dressing.  Category 1: Well dressed men, with a clear sense of style.  Category 2: Men who have learned the basics and are successfully avoiding the fashion "no's".  Category 3: Men who don't have a clue how to dress, and basically wear the kinds of things their mothers used to pick out for them when they were kids, supplemented by gifts and things that seem to fit and feel comfortable.  Category 1 is the rarest; categories 2 and 3 are more common.

Here's a strange fact.  In general, men in Category 1 are most attractive to me, men in Category 3 are second most attractive to me, and men in Category 2 are way in the back of the pack.  In some cases, Category 3 men are the most attractive.  That's counterintuitive, I know.  I'll explain more about this later, but for now, if you are a man who hasn't a clue how to dress himself, you needn't despair.   

Let's start with the basics: the fashion "no's" to which Category 3 men are blind.  Most of these are enduring principles.  A few are about trends, but I think should be heeded until a sharp dressed man or woman you trust, in your geographic area, tells you that the tide has turned.  (e.g., there is talk that pleated pants are coming back.  I am very suspicious of this, and even if it is true, it ain't true in Maine yet.) 

The basics:

    1) Your clothes should fit you.  Oversized T shirts are not attractive.  Too tight is not attractive, either, but too tight is better than too loose when it comes to knit tops.  Big, baggy, shapeless tops are no good.  Nor are pants that sag or gap.  Figure out what fits you and then pay attention to it.  Men's clothes are more consistent than womens' in terms of sizing, but there is still some variation across manufacturers, so you can't always assume that because a shirt at home that fits is a size medium, the medium at the store will fit the same way.

   2) The rules:  No pleated pants.  No white socks unless you're exercising.  No sneakers or hiking boots unless you're running or hiking.  You need leather shoes not only for dress up but also for wearing  casually around town.  No mock turtlenecks.  (Friends tell me the occasional mock turtleneck is permissible, but I am skeptical.)  No baggy sweaters.  Belt and shoes need to be the same color.  Dark socks only.  Button down shirts shouldn't have pockets on them.  No t-shirts with writing on them, unless you're running or at the gym.  (Category 1 men can and do and should break this rule with hip T-shirts.)  Outdoor gear is for outdoors, not for all the time.  No dark shirts or shiny shirts with a suit.  If you're in Category 3, shiny shirts are off limits to you entirely. 

    3) We'll get to how to be a Category 1 man in the next post.  But what am I forgetting in the basic advice?          

Comments

Your forgetting that people in Cat. 3, and probably in Cat. 2 won't pay attention to this.

[Thomas L. Vaultonburg]

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[Lynn]

Maybe this is just a personal preference... But I don't believe gentlemen should wear short-sleeve dress shirts. If it's too hot, roll up the sleeves or wear something else.

[Litoralis]

Ok...I generally agree, but why no pockets on dress shirts? I own a few Polo dress shirts that have no pocket, but I think pretty much every other dress shirt I own has a pocket.
And since you are a yacht club officer and should know this sort of thing...what is appropriate to wear on one's feet when wearing khaki shorts and a polo shirt after a regatta? I usually wear Reef sandals or leather boat shoes...what do you think?

[hkd]

My Dad, a family physician with his own practice, begain wearing short sleeved dress shirts to his office in the summer about 20 years ago. One of his patients actually wrote a letter of complaint to the local paper and a few others chimed in supporting the complaint. Unfortunately, neither the letters nor the protests of his daughters, got him back into long sleeves. He was a Category 3 fashion don't until the day he died.

[A.]

Oh, I don't know -- I think baggy khakis are pretty sexy. A little-too-large oxford shirt, too. I like the whole careless preppy vibe.

[girltuesday]

Sweaters that look like a Jackson Pollock painting gone wrong must be banned.

For the fashion-challenged of categories (2) and (3) noted above, who seek guidance, the "total outfit" stores can be helpful (think: J.Crew, Banana Republic). Equal parts preppy & meterosexual. And nary a pleated pant in sight.

[girltuesday]

Sweaters that look like a Jackson Pollock painting gone wrong must be banned.

For the fashion-challenged of categories (2) and (3) noted above, who seek guidance, the "total outfit" stores can be helpful (think: J.Crew, Banana Republic). Equal parts preppy & meterosexual. And nary a pleated pant in sight.

[girltuesday]

huh. don't know why my comment appeared twice? sorry . . . .

[turboglacier]

This pleats/no pleats business is totally out of control. I have, in my closet, somewhere around $1500 worth of pleated suits and pants. ALL were purchased within the past four years, and ALL under the direct supervision of women. Now, the women in my life are telling me that ALL of them must go to the Salvation Army.

In my interviews with men, and search of the web, I find that guys barely care about this, or are divided depending on body type. I believe we've become enslaved to fickle female fashion foibles. Does it impress women, somehow, to know that a man squanders cash to replace his wardrobe every two years because some little fabric nip is in, or out, or in again? Frankly, I think it's vile and wasteful. Marry such a guy and he's likely to choose new suits over sending the kids to college. Good idea?

A wise man once said, "Beware of all enterprises that require new clothes, and not rather a new wearer of clothes." At the risk of being labelled a frump, I must concur.

[wab]

Cheers for turboglacier. Where did this business of no pleats come from? Answer; some arbitrary fashion pundits paid by manufacturers to try to get men (or more likely get women to get men) to dump good clothes. My advice is the good fashion is fashion that looks good on you. If pleats are more flattering wear pleats, if no pleats flatter your body shape more, where no pleats.

I am surprised a more important rule has been omitted. "Don't wear cheap leather shoes" They look just that - inferior - and they are generally no too good for your feet either.

[Eleanor]

About the short-sleeved dress shirts -- my boyfriend wore one once, with a tie, for some school project, and the others promptly named him "Burger King Manager." I don't think he's worn one since.

[Al Wheeler]

Nothing wrong with pleats on suit trousers, but plenty wrong with off-the-rack pleated pants, most of which have the pleats going the wrong way.

[Ambrose]

Pleated pants make your ass look big. Unless you are pipe cleaner thin, they are a bad look that men get away with because they are wearing jackets. It's simple, really: More fabric means that the object being draped (in this case your butt) appears larger. Avoid pleats.

Also, baseball caps. These are fine if you are playing baseball, or otherwise engaged in some sort of outside activity where sun protection is important, but otherwise it's not a look that works. Besides, chicks think you're bald if you wear a baseball cap. If you are bald, be bald-- but don't go with that Paul Simon look. Nobody is fooled.

[tins]

somewhat wary of men who follow fashion too closely. a well-dressed man sticks with the classics with an emphasis on tailoring and the right accessories.

[a]

When in doubt: avoid patterns.

[Ben Duffy]

I should have read this post pefore posting to the 3rd installment on this topic!

Doh on me.

[Jason]

I think I fit in catagory 2 and am working my way up to catagory 1. I get complimented (by women) on how well put together I am all the time. I have to get in this pleats/no pleats argument.
Pants without pleats don't look good on me, I don't have hips and they seem to emphasize that fact. also it's embarassing to wear them without a jacket because they show off your package too much.

[Jason]

I think I fit in catagory 2 and am working my way up to catagory 1. I get complimented (by women) on how well put together I am all the time. I have to get in this pleats/no pleats argument.
Pants without pleats don't look good on me, I don't have hips and they seem to emphasize that fact. also it's embarassing to wear them without a jacket because they show off your package too much.

[bob]

Pleats/ No Pleats, I'l chime in too. While I know that no-pleats is more fashionable now, I'm yet to agree that you should never wear pleats. With suits, pleats are just fine, if the suit fits. Now, dress-pants or cords with pleats and no jacket are a different story. Women- hear this! If you walk into the majority of the expensive men's fine clothing store, and ask to see the most expensive suit in the store- it will have pleats! No-pleats is more popular with suit-seperates, and quasi-suit stores like Banana Republic, Club Monaco, and trendier (although not better quality) stores. I just bought a $1500 suit tonight, WITH pleats, and as a self-proclaimed Cat. 1 man, I'm proud of it!

[Moonraker]

I'm a Cat 1 man. I didn't use to be, but after my divorce four years ago, I made some changes in my life. I enjoy dressing well, and it makes me feel great as a person. I believe it's about self-respect. My idea of well-dressed is: Pair of dark grey jeans, a very white crisp dress shirt, a dark grey or black sport jacket and some very beautiful shoes. I have a few nice suits also.

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These are fine if you are playing baseball, or otherwise engaged in some sort of outside activity where sun protection is important, but otherwise it's not a look that works.

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Let's start with the basics: the fashion "no's" to which Category 3 men are blind. Most of these are enduring principles.

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