Four Dresses Women Should Never Wear

Or Men. Nobody Should Wear These Dresses

Keturah Hickman
May 05, 2026

My morning routine is very simple. I put on clean clothes 1. I brush my hair and put on a covering. I wash my face, brush my teeth, and sometimes apply a little face cream. I almost always spend more time on the baby than I do myself. And yet, I never feel bad about my appearance because I love the dresses I wear.

Even though I’m postpartum and have a little more weight than I’d like, my dresses help me maintain a positive mindset about my body. They’re comfortable and flattering even with the extra baby pounds.

The other day my husband and I were walking down the road when we saw a woman come out of her apartment. She had a full face of make-up, but her hair was piled high on her head and she was still in her pajamas. A common Upstate New York sight. My husband commented, “It astounds me when you can tell a woman spent an hour in front of the mirror but she still doesn’t looked ready for the day.”

I confess, putting on a dress is much easier than doing one’s make-up. However, just because it’s the lazy woman’s beauty hack doesn’t mean it’s not worthwhile. Putting on a dress and keeping your hair tidy is a statement. It’s choosing to be feminine while simultaneously avoiding vanity. It’s the best of all worlds.

However, not all dresses are equal.

Another time my husband and I were out shopping, he pointed to a woman ahead of us. “ She’s wearing a dress,” he said, “You should go talk to her and become her friend.”

Often I will do just that. But this time I shook my head. He seemed puzzled. I explained that there was a difference between a woman wearing a dress and a woman who wears dresses. I could easily make friends with women who wear dresses, but a woman who simply has a dress on for the day — and she often wears a specific type of dress I’d rarely if ever wear — might be weirded out if a stranger tried to make friends with her because of her fashion choice that day.

These are the things that only a woman can discern. No wonder we fascinate men.

If you want to be a woman who wears dresses, you have to fully embrace your femininity and beauty by only wearing dresses that are feminine and beautiful.

Here are four types of dresses (or skirts) I’d never wear and why.

1. Jean skirts

Jean skirts — especially the sort home-schooled girls live in — scream, “My mom won’t let me wear jeans.”

They are rarely paired with feminine blouses, but with sporty shirts or button-ups. The “look” is sealed with a pair of tennis shoes. Nothing about the outfit is “girly”.

I don’t like them for ideological reasons — they are usually cut to look as much like jeans as possible. Most girls I know who grew up in these skirts resented having to wear dresses, wore these as a “compromise”, and then exchanged them for the real deal as soon as they ran away from home.

I also don’t like them because they’re ugly. They look like a girl pulled a stiff, shapeless box down around her hips and knees.

If you want a denim skirt, I recommend something with ruffles or a-line gores. The denim skirt pictured in the upper left corner was sewn and made by Revivall, a company whose clothes and mission I adore.

2. High-Low

This dress is the barmaid meets pastor’s daughter. The uneven hem makes it seem safe for the church girls who want to flirt with their femininity without being accused of looking Amish. However, it draws all the attention to their knees, and unless your knees are extremely well-cared for, it is not a flattering spectacle.

When choosing the length of your dress, be decisive. It can’t be both short and long without looking ridiculous. For religious reasons, I don’t approve of mid-thigh but it certainly does a better job at revealing what one might want to see without focusing on the knees.

I understand wanting some texture to your skirt. There are ways to do this without it looking like the seamstress skimped on the fabric. Cascading ruffles, triangle shaped gores, etc are all great alternatives.

3. All Lace Formal Wear

The knee length lace dresses are often worn by women who never wear a dress until they’re forced to attend a wedding. Sometimes it’s an attempt to LARP as a blue-blood. The dress, though, is too tacky to be true formal attire. It is garish instead of elegant — everything about it is wrong from the often skin-toned under layer to the jarring difference of hem lines, odd sleeve lengths, and the mismatched necklines.

Lace is good, but this is too much lace. Remember, when trying to look elegant less is more.

Other formal wear to avoid unless: The mermaid dress, dropped waistlines, unusual sleeve cuts, etc. Most women I see wearing these dresses don’t have the right body type to pull them off. It’s better to stick with classic styles for formal wear. If you want unique features, choose an interesting neckline. Generally this is a safer option than messing with too much below the natural waistline.

If you want a nice dress for weddings, try silk or velvet and focus on simple aesthetics with one or two complex features. It’s good to have a hem length that looks good with heels which is usually mid-calf or past the ankle.

4. T-shirt Dress/ knit Skirt

I used to be a fan of the knit skirt before I understood that it was hardly any different than wearing a pair of leggings or sweat pants.

T-shirt and tank top dresses are included in this category — sure, they are all comfortable, but in a white-trash sort of way, and that just isn’t worth it. And they aren’t flattering on most body types (you have to be really skinny to pull it off). It’s more difficult to get away without wearing a bra with knit clothes, too.

If you want comfortable clothes that are becoming, decent, and dignified I recommend Super Cute Dresses (cotton spandex dresses, but they don’t cling to all your curves) or linen dresses (they hang loosely).

Love What You Wear

The goal should be to curate a closet you don’t want to throw away. Even if it takes years, every garment should make you feel beautiful. Most of them should be comfortable, too, as well as practical for your lifestyle.

Dress-wearing is a hack. It should bring out all your best feminine qualities. And so you should never feel frumpy or ugly or slovenly. Mostly you should never feel like it’s highlighting the wrongs parts of your body — knees and reproductive organs. The right dress will make you look and feel like a lady, and you will be able to wear it through the various stages of life from girlhood to motherhood.

If you’d like to embrace your femininity apologetically but need more ideas for flattering, visit out my guide for wearing a dresses.

Let me know what you think about the dresses and skirts I’ve shared. Is there anything you’d add (or take away) from the list?

Share this essay with your female friends as a conversation starter!

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