Since I am out and about a lot, I often see a lot. And what I see often gets me to the thinking about things.

Just the other night what I saw swirling around me in a packed watering hole got me to wondering how people evaluate the way they look for themselves when they go out.

Or should I rather say, it made me question how people can be sure that the look and fashions they put together for a given occasion are (a) effectively delivering the message they want to get across and (b) flattering. Bottom line: How do you know when you look good? And when do you know you look godawful?

I mean we all want to look good right? Why else would we work so hard at it? We change and change outfits, we get our hair cut, we pamper and primp ourselves, we shop, we dry clean, we press and we steam. So why don’t more people look…well…more stylish? My theory is that we don’t ask the right questions. So, since most people don’t ask themselves the right questions and make the appropriate adjustments, I’m going to ask them instead so each and everyone of you can privately be the judge of how successful your recent fashion statements have been.

Question # 1: What, if anything, do people say about the way you look when you go out?

Yes the world is full of liars. I know this. But I find that only the most malicious people (some of whom happen to be close personal friends of mine) will actually go out of their way to pay someone a dishonest compliment. I mean why go tell someone they look bad when you can just as easily stand in a corner, point and snicker at them?

At least 85% of the time I believe it’s safe to trust compliments from friends and strangers alike and that you should take cues from these compliments to help you understand what works best for you. Not that you should ever dress for other people (we’ll get to that later…keep reading), but you should be aware nonetheless of the times when folks are especially complimentary.

Likewise you should also be aware of what people are not saying. If you never ever get a fashion kudos from the people around you or from the random stranger on the street, you might want to start thinking makeover. In this instance, silence is anything but golden.

Caution: Also be aware that at least 10% of the time people give compliments simply because they don’t know what else to say. So take everything with a grain of salt.

Question #2: How do people respond to you when they see you?

Do people stare at you when you walk into a room? And how long do they stare? When people are introduced to you, do they look you up and down nervously or do they have pleasant smiles on their faces? All of the answers to these questions can provide cues as to whether your general appearance is usually in the winner’s circle or the loser’s circle.

In my experience, one of the most favorable responses one can hope for involves touch. When people constantly want to touch the fabric of an item you’re wearing or when they note the fabric of a garment when they go to hug you , you have definitely scored a fashion homerun (unless of course, the person ends up scratched and bleeding in which case you’ve struck out).

In any case the answer to the “response” question is only effective about 60% of the time because a good part of the time we have no way of knowing why the hell people are responding the way they do to us and an even greater part of the time most of those staring at us look like big ol’ messes themselves so we find ourselves not even caring what they think.

Question #3: Why are you wearing what you’re wearing?

Fundamentally one of the most people important questions in this bunch of self queries is why we honestly wear what we wear. Naturally, we choose different styles for ourselves because we think they look good, but most of the time we don’t go the extra step and think about why we find a particular style attractive and whether that style is right for us.

Ask yourself this… Does your attraction to a way of dressing have more to do with emulating someone else than it does with saying something about who you are? Moreover, do you even know what you want to say? Because if you don’t know your style, how can you possible expect other people to vibe with it? Which brings me to the final question…

Question #4: How does what you wear make you feel?

A real fashion icon, can and should stand out in a crowd. Audrey Hepburn and Cary Grant stood out because of their simply elegant approach to dressing. Katherine Hepburn stood out because of her classically casual style. And Cher has always made heads turn by being the most outlandishly sexy bitch in the room, no matter how many other sexy bitches are in the same room.

The best way to know how you look in an outfit is to gauge the way you feel in an outfit, because if you feel fierce, chances are other people will feel the same. Why? Because your confidence will shine through anything you could think of to drape your frame. Attitude is the foundation of style. I’ve said it a million times in this column, but it always bears repeating.

When you stand in front of a mirror and you genuinely like what you see staring back at you, you can be 100% sure that you do indeed know how you really look to the person that matters the most…. and that is you. (Damn what anybody else thinks… and that even includes old , overly analytical fashionistas like myself).

Until next time!