Alright, dare I go here? Dare a straight guy write a blog about dressing for a night out? The intelligent answer is ‘No’, but what the hell, let’s go for it. So, take this for what it’s worth. (A penny for your thought?)

Dressing is important as it not only gets us in the right mood, but it projects who we are. Yes, it is important who we are on the inside, but surely that great person on the inside wants to dress well so the outside matches?

For guys it is really not too hard. You can do a lot with a little. This is one area where it is much easier to be a guy. Yet, sadly, so many guys blow it still. One simple rule of thumb – It is always better to dress nice. I am not saying sport those Dockers and blue tie at the club Friday night, but T-shirts and tennis shoes have got to stay home. Guys have it easy, all we basically need are:
- Couple pairs of nice shoes (black and brown).
- 2-3 pair of nice jeans
- Black and/or other color of more dressy slacks (not business slacks)
- 5-6 nice shirts
- 1-2 blazers
Yes, yes, I know there are many more items, but these are the basics. You can add some ‘dress’ sneakers, vests, mi x in a tie now and then, etc, etc. But those are the basics. Like I said, guys have it easy.

Now for the ladies. Like all things involving the ladies, things are much more tricky. I may be wrong here, but I say dress for your mood and the event. I say this as I am out and about quite often. I can be at a formal/semi-formal fundraiser or a wild night on the town, in each of these I see some terrific ladies. Some really look terrific, and some miss the mark.

I am probably taking a much too much analytical approach to this, but when I think of how ladies dress, I think of two scales. Scale one is how dressy or casual they are and scale two is how sexy or conservative they are. So, bear with me here. With these two scales, we are left with four quadrants.
- Dressy and Conservative
- Casual and Conservative
- Dressy and Sexy
- Casual and Sexy

So, depending on your e mood and the event, you’ll be in primarily one of these quadrants. Or, if you are a real pro, you’ll layer or ‘de-layer’ to move between the quadrants as the fay/evening or your mood or alcohol level changes. [My personal ‘de-layering’ strategy is the transition from the Dressy / Conservative to the Dressy / Sexy – Off go the panties and blazer. Now we’re down to business.]

Not that this is the end all be all, but this just helps me as I look survey the field of lovely ladies. Each quadrant occupies an important event or part of the day, and dressing for each should be thought through. It is evident that some gals get this right. They are really thoughtful and they take the time to dress for the event and the mood they are in. Others’ seem to make little effort.

So, in the course of my day, whether I am solo or spending time with a lady friend, some of the events and moods may look like this:
Dressy and Conservative: Attending a fundraiser or business event. She looks good, conservative, but nice. Maybe a little sexy is trying to sneak in, but not too much. Like a good book, just makes me want to hang around a little more.

Casual and Conservative: Maybe this is lunch with friends/family or shopping. I often refer to this as ‘cute and colorful’. We can’t be too sexy here, so what we hold back on the sexy, we can pump up with the color. A little leg and/or cleavage is OK, but not too much.

Dressy and Sexy: My personal favorite, well I guess anything on the sexy scale is my favorite if the truth must be told. I think of this as the Saturday night sexy dress or the ‘sexy wife’ look. I really mean that as a compliment as there is nothing slutty about looking sexy, though some confuse the two. The girl with this look dresses great, there’s just not too much ‘quantity’ to what she is wearing, it’s all ‘quality’ baby. She’s strong. She’s sexy, she knows what she wants, and she’ll probably get it. Panties optional, at least after midnight.

Casual and Sexy: Maybe this is the Friday night outfit, or just a more casual venue, or perhaps this is hanging with a group of friends. Short jean skirt, tight jeans, low cut top, bustier top, backless halter, the list goes on. This chick is hot and she knows it. Always a happy ending here, at least for her.

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So ladies, we all know what it feels like getting ready to go out. We try incessantly to find the perfect shirt to go with that new skirt. When that’s not working, we swap the skirt for some skinny jeans and a chic belt. After glancing in the mirror again, we rustle through our closet, FINALLY finding our outfit of choice after trying on at least three (and ending up with a pile of clothes on the bed or corner chair to be dealt with at a later time.) And then we choose our shoes.

Now let’s think a moment about our shoes, shall we? A lot of places won’t even allow you in if you’re wearing flip flops or sneakers. And a sexy pair of heels would look amazing with that new skirt you finally decided to wear. They’d also look pretty hot if your night progressed into your wearing nothing but the heels themselves. When choosing your shoes, however, try to think beyond the initial impression. Choose wisely.

You have some idea before walking out that door of just how much you’re planning to drink throughout the evening. By all means, if you’re playing designated driver and can apply proper pressure on the gas and brake pedals while rocking six inch heels, go for it. If you are NOT D.D. for the evening, though, perhaps reconsider your footwear of choice. Because no matter how sexy you look walking out that door standing tall in those gorgeously sexy spikes, a couple hours later and a couple drinks in, you’re not going to look quite so hot tripping over yourself or falling into strangers. And unless you plan to tote a pair of those fold-up flats in your purse for your inevitably long walk back to the car, you can’t plan on taking off your stilettos and walking down the sidewalk. It looks tacky, and you just may end up with Hepatitis from some tossed away used needle laying around.

Here’s a little known fact for you, ladies. You know all those bruises that magically appear (usually somewhere on your legs and arms) after a fun night frolicking with friends? And you know how you can’t for the LIFE of you figure out where they came from, especially since you remember the entire evening? Well here’s your answer… it’s your shoes’ fault.

Your heel got caught in a sidewalk crack and you knocked into a street lamp. You seductively crossed your legs at a bar, but, in an attempt to not scratch yourself with the bottom of your stiletto spike, you kicked your leg up a bit too high and smashed your shin into the next bar-stool. You thought you’d look cute and sexy by sliding your legs to the other side of that three foot ledge you were sitting on, but you didn’t notice until you reached the other side that the ground was grass and your heel stuck in, forcing you onto your hands and knees on the freshly watered landscape.

Tall sexy shoes are not ALWAYS your friend. Choose your footwear responsibly. If you can’t bear to not wear your favorite spikes on a night out on the town, at least invest $10 in those folding flats that will fit in almost ANY purse. I promise you, the next time you want to wear your heels, they’ll look much better on without battle wound bruises from prior nights out.

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