For the Ladies: A Guide to Dressing to Please a Man

A woman in a blue dress and white hat sitting on the grass.

Quite possibly the most beautiful casual outfit a lady can wear.

Editor’s note: As an etiquette guide, this article is based on opinion. It’s goal is to create a standard.

I think I should start with a little disclaimer. I’m not advocating that women dress based exclusively on the opinions of men, or even that it should always be a factor. I’m offering guidance to help overcome modern women’s tendency to dress like their trying to be men or “courtesans,” and instead can look both attractive and respectable. 

Also, I’m not going to say much about practicality or the bedroom. Practicality should trump all. It’s better to wear pants and protect your legs than to wear a skirt and appear feminine. When you’re in the intimacy of the boudoir it’s all between you and your man, nobody else’s opinions matter. 

Femininity & Modesty

The ultimate guiding principle in ladies’ fashion should always be femininity. No matter what the situation a lady should always wear the most feminine outfit that’s both suitable and available, and she must never wear men’s clothes in public. 

Modesty can be thought of as the sartorial equivalent of humility. Just like humility is the middle ground between arrogance and self-loathing, modesty in ladies’ fashion is the middle ground between looking like a “lady of the evening” and looking like a prude. The goal is to accentuate your natural beauty while still looking like you have more to offer. Sometimes this can be a fine line, so tread lightly. 


Yes, pants deserve their own section. They represent the single largest change in ladies’ fashion over the last century. In the Victorian era women were expected to exclude themselves from certain activities because they would’ve required pants. Now, pants are standard for many women. The right norm falls somewhere in between. 

Pants aren’t very feminine, just short of the line into masculine.  On the flip side there aren’t any more practical alternatives. For that reason, ladies’ pants are inherently casual. Nice enough pants as part of a nice enough outfit can be equivalent to a man wearing khakis and a blazer but the equivalent of a suit requires a skirt or dress. 

Showing Some Skin

When it comes to how much skin a lady should show, less is more. Unless you’re Muslim and living in the Middle East, don’t go full shariah. If you’re thinking talking about what the minimum amount of skin to show is stupid then we’re probably on the same page. As long as you feel comfortable and unlikely to draw unwanted attention, you’re probably showing the right amount of skin. 

It gets a little more complicated when it comes to skirts. There are two things to consider; your age and the formality of the situation. As you get older and the situation gets more formal, your skirt should get longer. Knee length is never too long and only too short in the most formal settings.


Shorts are athletic and outdoorsy, so keep them for those situations. Shorts are really only a good idea if wearing a skirt would feel weird and pants would be uncomfortable. 

Makeup & Jewelry

This is another less is more situation. Wear a few pieces of jewelry but don’t get to the point where you end up looking like a walking pincushion. As for makeup, the point is to accentuate your own natural beauty so if you do it right nobody can tell until they see you without it. 


Here’s where you get to go nuts. There’s a plethora of attractive hairstyles for ladies. Going longer is generally preferred. Most short hairstyles are sorely lacking in femininity, or severely age you. When you’re doing your hair in the morning, remember that simple hairstyles are casual and elaborate hairstyles are formal. Personally, I like a woman’s hair to be curly and slightly longer than shoulder length, or perhaps down to the middle of her back. 

Along with hair it’s worth mentioning that a hat or fascinator is never a bad idea.

Your Most Important Accessory 

Time for some guessing. What’s your most important accessory? Your purse. Your shoes. Your glasses. Yes, I love a pretty bespectacled face but your most important accessory is your smile. I’m not saying you always have to look happy no matter how you feel. In fact, if a man loves you he’ll want to be there for you in the hard times. I’m saying the most important part of looking attractive is to carry yourself with confidence and exude charm and caring. There’s no better way to show this than a cute smile. 


One comment on “For the Ladies: A Guide to Dressing to Please a Man

  1. In lumina says:

    […] via For the Ladies: A Guide to Dressing to Please a Man — Reviving Manliness […]


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