Men: do you not know the first thing about dressing up? Ladies: are you sick of your man looking like a schlub? Want to dress better but don't know where to start? Look no further. I've compiled the following list of tips which, taken together, will go a long way towards making you look more like Conan O'Brien and less like Conan the Barbarian. If you're pressed for time (or are just efficient), all you really need to read is the bold-face text, but the subsequent explanations will add context and clarity.

1. Never, EVER button the bottom button of a single-breasted jacket.
Why not? Well, logically speaking, it's because a properly-tailored jacket is designed to flare out slightly at the hips, to give you more room when walking or sitting, so if you try to do up the bottom button, it will be too tight. But illogically speaking, you just don't do it. Period. It's just one of those rules. I didn't make it up; I'm just telling you so that you don't look silly to people who know the rules. (N.B.: For double-breasted jackets, all buttons should always be kept buttoned unless you're sitting down.)

2. The bottom tip of your tie should fall in the middle of your belt buckle.
This isn't always easy to accomplish for shorter men or men with small necks, because we don't tend to use up enough of the tie. The problem can often be solved by using a different tie knot. For most men, the knot they know how to tie—the one they were taught by their dad, or by some chagrined girlfriend 15 minutes before leaving for a semi-formal function—is the four-in-hand. It's a compact knot that forms an asymmetrical (scalene) triangle. Now, if you find yourself with too much tie, try the half-Windsor. It's a slightly more bulky knot that forms a symmetrical (isosceles) triangle. It also uses more of the length of your tie, because you wrap the tie around an extra time before finishing the knot. Result: no more sloppy extra length.

Bonus tip: Always allow yourself a minimum of 10 minutes to tie your tie. This prevents you from feeling rushed when you're getting ready, and gives you enough time to retie several times if you don't get it right the first time (and it will be a miracle if you do).

3. Chinos are not semi-formal, unless you wear them with a jacket.
"Chino" is the generic term for a khaki-style pant (i.e. one made of cotton) that's not khaki-coloured. If you're invited to a holiday party with a semi-formal dress code, wearing chinos with a dress shirt and tie is not good enough. At a minimum, you should wear dress pants. The only exception to this is when you're wearing chinos with an odd jacket (sport coat or blazer).

Bonus tip: An "odd jacket" is any jacket that is not part of a suit, i.e. not worn with trousers made from the same fabric. A "blazer" is a solid-coloured jacket with metal buttons. A "sport coat" is a patterned jacket with plastic, horn, or leather buttons. A solid-coloured jacket with plastic buttons of the same colour as its fabric should not, in most cases, be worn as an odd jacket.

4. Pleated pants don't look good on anyone.
If you're thin, pleated pants add bulk to your thighs and midsection. If you're not thin, pleated pants put more fabric and detailing in the area towards which you least want to draw attention. Flat-front pants look better on everyone, and are always correct.

5. These are not dress shoes.
These are casual slip-ons, and ugly ones at that. A dress shoe is (for the most part) plain, unembellished, simple, and elegant, ideally with a leather sole. If you only have one pair of dress shoes, they MUST lace up. (Some dress shoes are slip-ons, but these are for the most part monkstrap loafers, which are unusual enough that they should really only be your third or fourth pair of dress shoes.)

The following is the prototypical dress shoe, the Park Avenue model by Allen Edmonds:

The piece of leather across the toe part of the shoe is called a "cap toe." Plain black cap-toe laceups such as these are perfect for any formal or semi-formal occasion. They can be bought for less than $100 by manufacturers such as Florsheim and Bostonian. Please invest in a pair. If you only wear them a few times a year, they'll last a long time, and they'll never go out of style.

Bonus tip: Buy shoe trees as well. Shoe trees are spring-loaded pieces of cedar carved in the shape of feet, which you put into dress shoes while you're not wearing them so that they maintain their shape and don't crease too much where your foot bends. A $20 investment in a decent pair of shoe trees will dramatically extend the life of your shoes.

6. Nor are these dress socks.
The same socks that you'd wear with jeans or other casual pants are absolutely not acceptable for semi- or formal wear. You need dress socks, which are very thin, because they are designed not to interfere with the close fit of dress shoes. They are usually made of cotton, wool, or a rayon blend. (I personally swear by Calvin Klein socks, which can be gotten fairly cheaply at your local Winners/TJ Maxx/Marshalls/TK Maxx.) If you've never worn dress socks before, you may imagine at first that they feel like pantyhose. This feeling will go away. Please note that you should match the colour of your socks to your pants, not your shoes.

Bonus tip: Always wash dress socks inside-out in cold water to prevent fading.

7. A dress shirt collar is supposed to fit snugly.
This is so that, when you button the top button and put on a tie, there won't be a gap between the collar and your neck. If there is a visible gap between your collar and your neck anywhere around the circumference, your collar is too big. You should be able to fit two fingers in between the shirt and your neck, and that's all. If you want to be sure of a correct fit, have a friend take a flexible sewing tape measure and measure around your neck where a shirt collar would be. Note the measurement to the nearest half-inch. Now, when you go to a store to buy a shirt, buy a shirt which is sized one-half inch larger than your actual neck measurement. To ensure accuracy, you can unfold and unbutton the shirt, and then measure the back of the shirt's neck from the middle of the button to the middle of the buttonhole. Again, this should be one-half inch larger than your actual neck measurement.

Bonus tip: Your tie should always be darker than your shirt. If you must wear a very dark or black dress shirt, minimize the contrast between the shirt and tie. Also, always take dark dress shirts to the dry-cleaner so that they don't fade, and be sure to specify that you want them dry-cleaned, not laundered. Light-coloured dress shirts should be machine-washed on warm and hung to dry, never put in the dryer (unless you want them to shrink).

That's all for now. Check back soon, when I'll present the advanced version of this guide, with tips on how to make your suit fit like a movie star's.


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