In My Humble Opinion...

Style Guide for Women: Everything You Need To Know In Order to Dress Yourself


If Melania Trump’s Jacketgate reminded us of anything, it’s that there is a fair amount of confusion over what we should and shouldn’t be wearing at any given moment. From the type of event, to the hour of day, to the time of year, and even the season in life, confusion abounds when it comes to how we should dress ourselves.

The following fashion Q and A is designed to help set a few things straight.

When deciding what to wear should I dress for men or women? This is like asking, “When I’m ordering lunch, whose palate should I consider? My friend’s or the waiter’s?”

Although the answer has somehow managed to elude us for years, the answer is glaringly obvious. Dress for yourself. What do YOU feel comfortable in? What do YOU believe is appropriate for the occasion? What do YOU think looks good on you? You’re the one who is going to be trapped inside the outfit for hours. That means yours is the only opinion that matters.

Everyone else can mind their own business. Their opinion is relevant only when it comes to whatever they’re wearing. True, folks can decide whether they like your outfit or not, but that doesn’t mean they have any actual authority over you. Think about it this way: I can have opinions on the landscaping or paint jobs of the houses I pass on my way to work, but that doesn’t mean my opinion should influence anyone else’s right to landscape their yard or paint their house however they want.

Must I wear heels to dressy events? Conventional wisdom is, unless you have a note from your doctor confirming an actual medical condition, women are obligated to wear heels to dressier events, particularly in the evening—comfort be damned. But that’s as stupid as it sounds. The only time women absolutely must wear heels is …wait for it…NEVER.

Can you wear heels? Sure, if you feel like it. Again, note that the determining factor is how YOU feel. Hate heels? No problem. Don’t wear them. Love heels? Great! Rock them with confidence and enjoy.

When is styling my hair a must? Styling your hair is an absolute must when you want to have styled hair. Other than that, it’s optional. And if you’re on the fence about whether or not to go to the trouble, here’s a handy trick to help you decide: First, ask yourself this simple question: Do I feel like styling my hair? If the answer is yes, then proceed to the next question: Do I have time to style my hair? If the answer that question is also yes, then you should definitely style your hair.

Do I have to wear makeup? Please see answer to question #3, above. The same analysis applies.

When attending events that call for cocktail attire, do I have to wear shorter hemlines or show cleavage? Not if you don’t feel like it. Your skin is your own. When to show some and how much to show are entirely up to you.

When am I allowed to wear sleeveless shirts and dresses? Recently, a sales associate at Nordstrom told me that one thing she’s learned from working retail is that all women—even those who look objectively amazing—hate their bodies. And the part that they hate the most? Their arms. This is a result of decades of hideous messages from the “beauty” industry, and it makes me both sad for us and mad at them.

So, the answer to the question of whether you’re “allowed” to go sleeveless is a very strong hell yes. If, however, you are uncomfortable doing so, then, hey, no pressure. But you might want to examine your discomfort to determine whether your feelings are truly your own, or rather the result of internalizing all the bullshit the “beauty” industry has been selling.

How do I know when certain items in my wardrobe are no longer in fashion and should be retired? When an article of clothing is no longer in fashion and when it should be retired are actually two separate questions. Let’s take them in order. Previous answers notwithstanding, it is true that fashion actually changes over time. Hemlines go up and down and pant leg widths go in and out. Some people care about this very much, others don’t care at all, and still others fall somewhere in the middle.

The fashion industry, however, is financially incentivized to care about this 100% of the time, and does its best to manipulate everyone into thinking that caring about fashion is mandatory. It’s not. Much like gardening or cooking, fashion is an interest, and it’s up to each individual to choose whether and how much interest you have in it.

If you have an interest in fashion, you can determine whether something is in or out of style be keeping up with style blogs and magazines. But make sure you read those with caution. Lots of attempts to manipulate you are embedded in these forums.

When it comes to whether something should be retired, however, the analysis is different. For this, what matters is whether you’re tired of it. When you put on an article of clothing and look in the mirror, how do you feel? If you like what you see, then it’s still got life left in it. If you don’t, then it’s time to take it out of rotation.

Where can I find the rules for what I should and shouldn’t wear based on how old I am? People who tell you that there is some sort of sliding scale for necklines or hemlines depending on your age are trying to put their rules on you. Don’t let them. It’s up to you to decide what looks and feels right for you.

There are no age-based rules; there are only comfort-based rules. But remember, comfort includes more than just how something physically feels. What you are wearing can also affect your mood. When it comes to physical comfort, your super soft bathrobe may win first place, but wearing your bathrobe to a business meeting might make you feel oddly out of step. Those feelings matter, too.

No matter how old you are, when you are deciding what to wear you need only to take into consideration the affect your wardrobe choice will have on your physical comfort and your mood and no one else’s.

How much weight should I give to other people’s opinions? The first thing to know here is that there’s a difference between opinion and information. For example, if you’re headed to a party on October 31st dressed like a naughty nurse and your friend tells you the event is not a costume party, that counts as passing along information. If, on the other hand, you are headed to a cocktail party and your friend tells you your dress isn’t vavoomish enough, that’s an opinion.

When it comes to an opinion, what matters is whether you asked for it. If you did, and they’re nice enough to go to the time and effort to give it to you, manners dictate you give it due consideration. You’re not obligated to take their advice, of course, but you should at least consider what they’re saying—especially since you obviously respect them enough to ask for their opinion in the first place.

Remember, each and every one of us has exclusive jurisdiction over what we wear. That means no one has the right to tell you what to wear, and you don’t have the right to tell anyone else what to wear, either. The sooner everyone gets that message, the better off everyone will be.

By dressing the way you want to dress you will actually help be the change you want to see.