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.


Dressing Your Kids to Enjoy Their Childhood and Become Mature Adults

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

Everyone has opinions on how children should be dressed. Some are ridiculous and some are reasonable so it can be hard to sort them out. I’m going to be throwing my hat into that ring and trying to guide you into dressing your children to ease them into the adult world without keeping them from playing.

Complement the Adults

You and your wife likely put a lot of thought into how you dress, but how do your kids fit into that? If they’re dressed better than you it’ll look like you’re trying to show them off, if they’re dressed worse it looks like they don’t really matter to you, and if they’re dressed as well as you but totally different it looks like their very presence was an afterthought. You’ll want to make sure you have at least one outfit to go with every outfit in your child’s wardrobe. You don’t have to coordinate like they’re an accessory, so long as you’re both dressed to the same standard.

For girls that’s pretty easy, a cute dress goes from the playground to church, but boys are harder. If your son’s wearing a more juvenile version of what you would wear, then you’re probably good.

Span Formality

Children’s clothes seem to rarely go beyond the realm of the casual, but they should. Don’t buy your kids any formalwear they won’t use soon, but they do need at least one church-ready outfit. By “church-ready” I don’t mean your church, but rather any church. Every girl needs at least one nice dress, and every boy needs at least one outfit with a tie. Kids clothes are flexible in terms of formality, so whatever they’d wear to a more formal church would probably work right through black-tie optional and maybe even beyond.

Keep It Modest

Children are not sexual beings, so they’re likely to internalise everything about their childhood as being non-sexual, so long as it doesn’t cross the line into molestation. If you dress your young daughter in skimpy outfits than she’ll likely dress even skimpier as an adult. Essentially, hold children to the same standards you would adults.

Move Towards Adult Standards

The long term goal is obviously that your children dress appropriately as adults. To that end, every fashion decision you make for them needs to be a step in that direction. The only case in which it’s acceptable to dress a child significantly different than an adult is if that difference would later be abandoned entirely. If how you dress and how you dress your child are sending them mixed messages, they’ll end up taking the path of least resistance and make sartorially apathetic choices as an adult. You will have created the type of person that wears pyjamas in public and t-shirts in church.

Put Practicality First

This is where the enjoyment of childhood really comes in to view. Children will always want to play and you don’t want to quash that enthusiasm. So, be sure everything they wear allows for that. Don’t dress them in anything that appreciably restricts their movements, unless that’s the only way they can be dressed appropriately. Also, choose your daughters’ skirt length with that in mind. You don’t want it dragging on the ground and getting caught on things, but you don’t want her constantly flashing her playmates either. 

Summer: Dressing for the Heat

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

Summer is here, and it’s brought the heat with it. If you’re not dressed for it you end up baking like your grandma’s rhubarb pie. I’m going to help you dress comfortably in warm weather without looking like a cad.

Keep Your Shirt On

There’s a trend these days of guys taking their shirts off any time it gets warm. Often these guys are pretty out of shape too. I say, don’t. Unless you’re at the beach or pool or maybe playing a pickup basketball game, keep your shirt on. Nobody wants to see that anyway. You’re a man, your intellect and character make you far more attractive than your body ever could.

Choosing Your Fabrics

Your choice of fabric can greatly influence your comfort level in any weather conditions. When choosing fabrics for warm weather, you’ll want to wear something light and breathable. Cotton is a good choice, as are certain synthetics. You want to be careful with the synthetics though, they can look excessively casual. Lighter colours are a wise choice as well, as darker colours will heat up more in the sun.

Wear a Hat

In the heat, hats go from a wise fashion choice to a necessity. The right hat will protect your head from the harsh sun. A baseball cap would do the job, but there’s not much that’s less classy than a ball cap as an everyday hat. A gentlemanly white Panama hat is probably your best bet. It’s summery looking but still classy, and it goes with a wide variety of casual and informal outfits. On top of that, you’ll look a bit like Al Capone. 


Shorts are far more comfortable in the heat than pants but can easily be worn wrong. It’s sad that I have to say this but, shorts are exclusively casual. In fact, you should probably limit them to your street clothes. A man’s shorts should be approximately knee length with a relaxed but not baggy fit. You have a little bit of leeway on the baggy side but otherwise they’ll almost instantly look ill-fitting. You also need to remember that simpler garments are more formal, so only pair cargo shorts with t-shirts. Personally, I would always go straight to pants after cargo shorts. Finally, never tuck your shirt into your shorts.


Sandals are an excellent choice to keep your feet cool in the heat, but there are rules here too. Most importantly, there are two garments that must never be worn with sandals; socks and pants, you’ll just end up looking like an old man, even if you’re thirteen. Leather flip-flops or hiking sandals are a touch more formal so they’re a good choice with a polo or button-down shirt. Anything else is best kept in the realm of t-shirts.

Be Prepared to Layer

Even the hottest days can get pretty cool in the evenings, so you’ll need to be ready for that too. If you expect to be out into the evening, be sure to bring along a sweater or coat that goes with your outfit. Fit is less of an issue since you’ll be most comfortable wearing only one layer anyway. If you’re going out on a date, a blanket is your best choice so you can cuddle up with that lovely lady when it gets cool.

Suck It Up

Sometimes you may have no choice but to tap into your inner stoic, and suck it up. Men’s fashion gets inherently warm once you get up to the more formal end. It can even be enough to make you jealous of the fairer sex and their light airy dresses. Just carry a handkerchief and try to stay indoors. 

Fashion Staples Every Man Should Have

A lot of men’s wardrobes seem to be nothing but jeans and t-shirts, but they still have no desire to expand it. I’m still in the process of expanding my own and through that consideration I’ve gotten some extraordinary insight and have come up with this list of fashion staples Every Man should have.


These are the things you really should have at the ready, regardless of what culture you live in, because you may need them on too short of notice to go shopping.

Black Suit

A black suit is really irreplaceable. They almost form their own level of formality and to some people, including me, they’re the only thing that’s appropriate at a funeral. You’ll probably want to go with a two or three button single breasted jack with notch lapels.

Dark Suit

A black suit isn’t always appropriate, especially in some cultures where they’re considered exclusively funeral attire. For that reason, you’ll want to have a charcoal grey or navy blue suit in your closet for those other occasions.

Dress Shirts

You need to have a variety of dress shirts to go with various outfits. Be sure to include at least one solid white shirt and several more of other solid colours. If you want to throw in some patterns, feel free, just keep the patterns subtle.

Ties & Pocket Squares

You’ll need these to complete your suits. They’re also the best place to add bold colours and patterns.


I recommend having at least two belts. A woven fibre belt for street clothes and a leather one for casual and semi-formal. Your belt should match your shoes, so you may need more right there. You’ll also need more belts if neither of those work with some of the outfits in your wardrobe.


Blue jeans only. A man should only wear other colours of denim if he has a very good reason. The exact style and fit is a personal choice but every man should stay away from skinny jeans.


I mean a variety of sweaters, from sweatshirts to wool crew necks. Every outfit you have should have a sweater to go with it.


You’ll need t-shirts for cases where comfort should trump style. They can also be incorporated into casual outfits in some very expressive ways.


Most men don’t need many shorts, since they’re inherently so extremely casual. Whatever shorts you have should be approximately knee length and fairly loose.


Every man should have at least one blazer. A classic navy blue is a good choice, but there are so many options that every man can have a blazer that perfectly suits him.

Sport Coats

In the same vein, every man should have some sport coats. A sport coat or two can be combined with virtually any outfit to create something classy but expressive.


In addition to jeans, shorts, and suit pants, every man needs some nice trousers. Jeans and shorts are often inappropriate and suit pants should only be worn with their matching jackets so they wear evenly.


For obvious reasons, every man needs coats. After all, you don’t want to freeze to death, I hope. Exactly what coats you need depend on where you live but they should include coats to go with every outfit and all weather conditions.


Unless you never go outside, you need some shoes. If you actually never go outside, start. You’ll want at least a pair of oxfords or derbies, a pair of canvas sneakers, a pair of athletic shoes, a pair of work boots, and a pair of hiking boots, in colours that match your belts and coordinate with your pants. It’s also a good idea to have sandals and some more unique dress shoes, like Chelsea boots.


I’ve said it before, every man should wear a hat. For that you need to own some. You want at least one casual hat, one informal hat, and one hat to go with your street clothes. You can’t have too many hats though so go nuts, just be sure to wear them appropriately.

Sporting Attire

Since every man should be ready to play sports, he needs to have at least one appropriate outfit in his wardrobe. You’ll also want to have the traditional attire for any sport you play frequently and the uniforms for any organised team sports you play.


You’ll likely want to have two pairs of sunglasses. For practical reasons, like sports, you’ll want to have some more rugged sunglasses but you’ll want some nicer ones too. Your standard sunglasses should be something with metal frames and black or mirrored lenses, like classic aviators.

Traditional Attire

If you’re closely associated with a culture that has traditional clothing, like Scottish kilts or Japanese yukatas, you need to be sure you have that too.

Get When You Can

There are some things that you really should have in your wardrobe but you’ll almost certainly have time to shop for when you need them.


The classic tuxedo is the standard of evening semi-formal attire. It consists of black pants with a satin stripe on the outseams, a matching jacket with satin lapel facings, and a black bow tie and waistcoat.


If you don’t know what a stroller is, it’s the daytime equivalent of a tuxedo. It includes a black suit jacket, grey trousers (usually striped or checked), and a four in hand tie and waistcoat (usually grey, black, or buff in colour).

Evening Dress

No, I don’t mean an actual dress. Evening dress typically refers to men’s evening formalwear. It’s identical to a tuxedo but with a tailcoat, and white waistcoat and bow tie.

Morning Dress

Again, the daytime formal standard is very similar to its semi-formal equivalent. The only common difference this time is the use of a tailcoat. It also has more acceptable variation.

More Hats

Naturally, when you have more outfits you may need more hats to go with them. For formal and semi-formal you’ll likely want to go with a bowler, homburg, and top hat.

More Shoes

Again, adding outfits may necessitate adding more shoes to your wardrobe as well.

That’s my list of men’s fashion staples. I didn’t mention anything about uniforms because you either need them immediately or not at all. If you have anything to add to this list, feel free to add it in the comments.