For the Ladies: Dressing for a Date

Something that baffles me about the world of women’s fashion is how little voice straight men get. What’s even more ridiculous is that gay men are seen as experts, despite being incapable of having insight into the aesthetics or comfort of women’s clothes. Usually it just means men won’t like how they dress and it’s not a problem, but on a date the exact opposite is true. When you’re on a date, you’re selling yourself, you want him to like you. Obviously, nobody knows better what men like to see than men. I’m going to give you a few points to think about, some tips, and even end off with some suggested outfits. I’ve written about what men like to see but this will be assuming you’re looking to have him be interested in marrying you. 

What Has He Told You?

What he’s told you about his plans for your date and his preferences for women’s clothes can tell you a lot. Always dress appropriately for whatever activities he has planned, even if that would go against any of the other “rules” for dating attire. Also, feel free to ask him if it matters how you dress. If it does, he’ll tell you.

Be Yourself

You may be selling yourself, but you’re not a used car salesman. Don’t dress in any manner that you would consider inappropriate or weird. If you would have to cease being yourself to be his wife or girlfriend, then he’s probably not the guy for you.

The most important point here is that you have to dress for the body you have. Your goal is to accentuate your natural beauty, not create false beauty. Chances are, that’s well within your abilities. If that’s not good enough for him it could be the kick in the pants you need to lose some weight, but most likely he’s just a jerk that’s really just looking for a living sex toy.

Try For Sexy, Not Slutty

Sex is an inherent part of dating. No matter what he says or how wonderful a guy he is, staying with him means spending quite a bit of time in bed with him. On the other hand, any real man wants a woman who brings more to the table than just sensuality. You’ll need to walk the fine line between sexy and slutty. Showing some cleavage and leg is a good idea but don’t take either too far.

There are easy rules of thumb to know if you’re dressed too slutty or sexy enough. You look sexy if he’d accept an invitation to your bed, if looks are all he’s considering. You look slutty if you wouldn’t want your father to see you.

Go Easy on the Makeup

One of the quickest ways to go from sexy to slutty is to overdo your makeup. The point of makeup is, once again, to accentuate your natural beauty. You want to draw his attention to your face’s best features and away from your flaws, assuming you have any. If you did your makeup perfectly, he won’t be sure you aren’t so naturally beautiful that you don’t have need of makeup.

Wear a Skirt

Here’s where we get into the practical advice. Any man worth having, is looking for femininity, and there’s nothing more feminine than the skirt. Even so, it’s fine to wear pants if the activity calls for it or you’d never wear a skirt otherwise, given a reasonable option. It doesn’t matter what kind of skirt it is, or even whether it’s part of a dress or just a skirt worn with a nice top. Personally, I think a nice dress is the best way to go.

Dress Nice

People tend to pay particularly close attention to how they dress for job interviews, and when you think about it dating is essentially the same situation. The only differences are that it’s the most important job of your life, and there’s no chance for retirement, resignation, or dismissal. You’re trying to convince him that you should be his wife and the mother of his children, you should dress appropriately, considering something so important is at stake.

This is the time to break out one of your nicest dresses. Go ahead and wear those earrings you never get to. You’ve found yourself in the only situation where your looks should be of crucial importance.

Do You Need a Purse?

When you’re on a date, you may not need a purse. As long as he’s taking you out, you won’t need to bring any money or your debit card. You shouldn’t be using your phone on a date. I don’t know what you carry in your purse, but there’s a good chance you won’t need any of it, so a purse is just something to carry around.

Some Suggested Outfits

I can’t tell you exactly how you should dress, but these are some excellent options for a nice but modest dinner, or other classy date.

In Warm Weather

Wear a light sleeveless dress, something with a more flowing skirt. Pair that with some high heel or wedge sandals and a sun hat.

In Cool Weather

When the weather gets a little bit colder, you’ll want to switch to a heavy fabric for your dress, and maybe add sleeves. You’ll also want to add a light jacket. It’s also a good time to break out those tall black boots every woman seems to have, especially if they have a bit of a heel.

In Cold Weather

When it gets cold out, you definitely want to wear tights or stockings. Closed toe shoes are also a good idea, especially if there’s snow on the ground. Choose a heavier coat and a dress that won’t be crushed by it. As tempting as it may be, don’t wear any sort of hat that’ll mess up your hair. Keeping warm shouldn’t be a problem. If he’s worth having, he’ll try to keep things indoors when anything more than tights and sleeves are needed to be comfortable outdoors.


For The Ladies: Dressing Up

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

I’ve written about how a lady should dress when she’s concerned about men’s opinions and dress formality but never both at once, so here it is. Today, I bring any interested ladies some guidance for dressing to meet the codes of dress formality.


Here’s one place where men’s and ladies’ dress codes work differently. The wider variety of options means very similar outfits can be different levels of formality. Fit is the main distinction here. Tighter tops and looser skirts are more formal than looser tops and tighter skirts, although the tightest should be reserved for younger ladies. The correct fit for pants and shorts is entirely based on style.

Practical Attire

In the world of practical attire, form follows function. The priority is for your clothes to be suitable for your activities, no matter what you look like. This is where all athletic attire needs to stay. It’s also a good place for shorts to stay.

Street Clothes

Street clothes are what you wear in the absolute most casual situations, like running errands. They’re also the most formal attire where shorts, sweatshirts, and t-shirts and all forms of tanks as top layers, are appropriate.


When you get into casual then aesthetics take priority. This is also the point where it becomes important to pay attention to hair and makeup. Casual’s also the limit for pants. You can get a pretty good smart casual outfit with pants but you can’t get more formal than that. It’s also where you should leave the denim skirts and the like.


Informal is where men would be wearing suits so it’s most appropriate for ladies to dress similarly, but with skirts and no ties. Simple dresses are also quite appropriate, as are dresses that are more elaborate but in a more trendy way.

Once again, there’s something that shouldn’t pass this level. This time it’s separate skirts and tops. If you’re trying to go beyond informal then you need to wear a dress.

Semi-Formal & Formal

Just like for men, semi-formal and formal attire for ladies is more uniform, but for ladies the difference between daytime and evening is more pronounced. The best thing for daytime semi-formal is a cocktail dress with about a knee length skirt. For evening semi-formal and daytime formal, an ankle length evening gown is best, and for the evening you should transition to a floor length ball gown. If you’re wondering what the difference is, go back to the section on fit and that’s a simple version. Just remember that added accents and better materials make a dress more formal.
Another difference between men’s and ladies’ formalwear is that ladies should wear more elaborate attire to dress more formally. It’s also a good idea to wear gloves, even indoors, with more formal attire but you can put together a nice semi-formal or daytime formal outfit with them.

Jewellery & Accessories

For the most part less is more when it comes to accessories, but it’s not quite that simple. When you want to dress more formal you should go a little bit further with jewellery than you normally would. Also, you want to reserve the elaborate and rough material purses for your more casual outfits, and you may want to consider leaving your everyday carry up to your man for more formal occasions. 

Hats: For Gentlemen and Ladies

Older gentleman reading World War Two newspaper on the bus.
Editor’s note: As an etiquette guide, this article is based on opinion. It’s goal is to create a standard.

When we look at the manliest men in history, many of them wore hats. Teddy Roosevelt, Wyatt Earp, and Frank Sinatra all wore hats frequently. Why then have hats fallen out of favour? I can’t give you an answer because there’s no good reason for it. So let’s put our hats back on and exude the class the fashion world has been trying to extinguish and start wearing outfits that look well thought out and finished.

For Gentlemen

It’s not always appropriate for a gentleman to wear a hat. He must never wear one when in an office, home, or church, when eating a meal, or for prayer. When coming or going, or in any other indoor space, it’s at his discretion. A gentleman can also use his hat in greeting, but I’ll talk about that in other article. Most importantly, a man should always wear a hat if it’s appropriate.

Like all men’s fashion, subtlety rules in hats. A man’s hat should be mostly neutral colours. A colourful accent piece is fine so long as it doesn’t clash with the rest of his outfit. More colourful and elaborate hats should be kept to casual outfits, where the distinction between men’s and ladies’ hats begins to blur.

Some good hats for a gentleman to have in his wardrobe are fedoras, homburgs, top hats, bowlers, and flat caps or anything along those lines. Trilbys have become associated with some pretty unmanly boys and classless women, so they’re best avoided.

For Ladies

Ladies’ hats can be far more flamboyant than men’s, just don’t start looking like the Chiquita Banana lady. When it comes to colour, a lady’s hat should at least complement, if not, match the dominant colour in her outfit. Pill box hats and sun hats are good go tos, although sun hats are fairly casual. Fascinators, although not technically hats, are also a great option to go with more formal outfits. Unlike gentlemen, ladies generally only remove large hats when coming indoors, and can wear their hat all day, but wearing a more arranged hairstyle in place of a hat is also acceptable.

For Everyone

When we get into casual hats it becomes acceptable for men and ladies to wear the same hats. Large or flamboyant hats should be reserved for ladies. Baseball caps are very popular casual hats but they should actually be reserved for athletic contexts. Flat caps should be reserved for men and what’s formal for one gender is not casual for the other. Western hats should be reserved for western themed events and activities like ranching and horseback riding, unless you live somewhere like Texas, Arizona, or Alberta. One thing that’s crucial to remember, any branding beyond a maker’s mark expresses a strong association or affinity, so don’t wear any logo simply because it’s fashionable.

Cultural & Uniform Headdress

If you come from a culture with a strong association with a specific style of headwear then go ahead and wear it in accordance with its traditional etiquette, even if it conflicts with typical etiquette. If you’re authorised to wear a uniform that includes headdress, then do it in accordance with regulations, but never wear obviously uniform headwear if you shouldn’t wear the whole uniform.

My Hats

You may be wondering what hats I wear, and when I wear what. So, here’s what I have and what I plan to get.

What I Have

US Army surplus camouflage patrol cap (street clothes)

Charcoal grey flat cap (casual)

Black fedora (informal)

What I Want

Grey homburg (evening semi-formal)

Black bowler (daytime semi-formal)

Black top hat (formal)

Grey fedora (casual)

Royal Canadian Navy uniform headdress

Black and brown cowboy hats (practical attire, specifically riding)

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. 

What is a Lady?

Lady sharing tea with a gentleman.
There are two other types of people that it’s important to define to contrast with men. I’ve already discussed boys but defining a lady is also important. In the simplest terms; a lady is to a girl as a man is to a boy, but there’s more to it than that. This can be a guide to becoming the kind of woman that deserves a real man, or a checklist for finding a woman like that. 

What a Lady is Not

Possibly more important than what a lady is, is what a lady is not. This can be summarised quite easily; a lady knows and acts like she has value. She is not a possession. She is a person and thus her well-being is of concern beyond how it effects others, and she considers her own good when she must make a decision. She is not a slave. When she serves it is because she sees values in the service or enjoys serving. 

A Lady Accepts That She Will Never Be A Man

There may be debate over whether or not a person’s gender can ever truly change, but one thing that is clearly true is that anyone with a woman’s body cannot be a man. That’s not to say that a lady can’t have things in common with men or have traditionally manly interests, it just means that she is inherently excluded from any group defined as being made up of men. It’s quite common that women want to be a part of all male groups and activities, unaware that their very presence fundamentally alters the group dynamic. 

Also part of that is acknowledging the inherent differences between the sexes. I’m not saying that all traditional gender roles must be universally observed, but rather being aware of the differences that may have led to them is necessary. Mostly it means that sometimes gender may be directly relevant. A perfect example of this is the intentional male space, some women believe they need such spaces as well, not acknowledging that intentional male spaces exist because the natural male spaces have become female spaces. When women are present in male environments, they become female environments. 

A Lady is Beautiful

That’s not to say that if a woman doesn’t have alabaster skin, fiery locks, and a perfect figure she can’t be a lady, but rather that a lady takes pride in her appearance. As far as I’m aware, there’s no such thing as a healthy woman who can’t be beautiful if she tries. On the other hand, there’s also no such thing as a woman that all men find equally attractive, but there’s no need for that anyway. Part of that is embracing her femininity. There’s no denying that female and male bodies are different and a lady takes pride in that. When a woman wears women’s clothing that suits her body she tends to look beautiful and confident, but when she wears men’s clothes she sends the message that she’s ashamed of her body. 

As formality increases, so should the differentiation in men’s and ladies’ appearance. On the extreme casual end simply wearing gender appropriate variants of the same clothing is fine, but there should be no similarity at the formal end. 

A Lady Embraces the Roles She Accepts

This mostly applies to gender dynamics, but it’s somewhat relevant all the time. Most of the time it’s pretty obvious what roles she’s accepted but in a marriage it’s less so. When a lady gets married she either comes to an agreement with her husband about how labour is to be divided in their household, or they both accept the traditional gender roles. I’m not saying that there’s a universal “right” division of labour, but rather that the traditional gender roles should be treated as the assumed default. Virtually any roles can work with mutual consent, although it can be hard to stop the “househusband” role from becoming emasculating. 

A Lady is Moral

Defining morality can be a very difficult issue, so I’m not going to try. A lady’s morality is always held to a high standard. The same general morality should apply to men and ladies, beyond the simple willingness to differentiate. The one area that deserves to be mentioned is sex. A lady reserves all sexuality beyond a kiss for committed relationships and doesn’t embrace her full sexuality until marriage. 

A Lady is Supportive

They say behind every great man is a great woman, and that’s true. A lady has her man’s back. Her man will stand up for her as well. It goes both ways.