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20 Clothing Items That Humble Our Most Confident Dressers


20 Clothing Items That Humble Our Most Confident Dressers


Say “Maybe” To The Dress

Confidence is everything, and you should always feel good about what you’re wearing. Unfortunately, a lot of clothes aren’t made to make you feel good, either by making things too loose or too tight, sitting in odd places, or needing to constantly be readjusted. Even the most self-assured dresser can have trouble with these fashionable items.

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1. Skinny Jeans

The iconic pants of the 2000s and 2010s, skinny jeans, will give anyone a run for their money. They might look good once they’re on, but anyone who has worn these tight-fitting pants remembers the 10-minute struggle to pull them up their legs, leaving you sweaty and a little embarrassed.

woman in blue denim jeans and white converse all star high top sneakers sitting on orangeLaura Chouette on Unsplash

2. Bodycon Dresses

While they can be comfortable in terms of fabric, bodycon dresses have an incredible ability to highlight just about any aspect of your body you would rather not have highlighted. Not to mention, the annoying bra and underwear lines tend to leave you feeling rather exposed.

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3. High Heels

The ultimate shoe for work or formal occasions that ultimately leaves you with blisters and bruises. High heels may look pretty, but staggering around like a baby deer leaves less to be desired. Even a constant heels wearer is at risk of getting caught in something like a sewer grate.

woman in black leather heeled shoesLaura Chouette on Unsplash

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4. Pencil Skirts

They may be good for office wear, but like bodycon dresses, they tend to show off the parts you’d rather keep hidden. Also, they’re so uncomfortable to sit down in, nearly requiring a lesson in how to gracefully get in and out of a chair if you’re planning on wearing one.

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5. Peplum Tops

These were all the rage in the early 2010s, often popularised by the boho-chic, hipster style that dominated 2011-2013. Today, we’re much wiser, often noting that peplum tops can create an unflattering, cupcake-esque shape in your midriff section.

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6. Berets

Unfortunately, not everyone can pull off a beret. We’re not sure what it is, whether you’re unable to wear it correctly or simply don’t have the personality to pull it off, these adorable French hats just aren’t for everybody. Luckily, you’ll be able to tell right off the bat if you can wear one or not.

woman in black spaghetti strap dress holding coca cola bottleVladimir Yelizarov on Unsplash

7. Strapless Tops

Strapless anything means you’re in for a rough night of continuously pulling your shirt/bra/etc up, only to have it slide right down again. If you’re lucky enough to have a strapless top that doesn’t fall, it very likely means you’re dealing with icky plastic rubbing against your skin all night, which is also not pleasant.

Young woman in a checkered dress kneeling outdoorsFaustina Okeke on Unsplash

8. Gaping Shirts

A button-up is a great way to dress up a pair of jeans for work, but what happens if you’re unable to keep it together? We mean this literally, as any of our larger-chested readers know, that a shirt will be a perfect fit everywhere—except at the bust. This means you either get to deal with an unpleasant gap in your shirt, or you have to look bunchy by going a size up.

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9. T-shirt Dresses

They are incredibly comfortable, but they're not always the most flattering. While t-shirt dresses are a great way to be able to run out and do errands, you’ll often feel a little bit like a square. Sure, you could create a silhouette with a simple belt, but that defeats the purpose of this otherwise cosy outfit.

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10. Leggings

Yes, we know that leggings are like the ultimate comfort bottom. However, anyone who’s had multiple pairs of leggings knows that loose, see-through, or bunchy leggings are the bane of your existence. Not only are you showing your patterned undies at the gym, but you have to stop mid-set to make sure they don’t fall off.

woman in gray and black long sleeve shirt and black leggings sitting on white concrete benchRyan Hoffman on Unsplash

11. Mini Skirts

These skirts are so cute and look positively adorable on anyone. However, if you have a bigger backside, you may often feel a little too revealed in this small piece of fabric. What good is wearing a mini skirt if you’re spending the whole time worried if your butt is on display?

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12. Knee-High Boots

This problem comes in twofold. One, regular knee-high boots are super cute, but can humble anyone with larger or athletic calves. The slouchy knee-high boot is also an issue, as you’ll spend your entire day pulling them up to where they're supposed to be sitting.

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13. Short Shorts

Like the mini skirt, short shorts can look cute on anybody, but they also run the risk of revealing something you don’t want revealed. Alternatively, you may have a problem with the shorts riding up your backside, leaving you with a less-than-favourable wedgie you now have to fish out.

woman in blue and white dress sitting on brown wooden benchAlexey Elfimov on Unsplash

14. Bras

Bras are widely considered to be one of the most uncomfortable pieces of clothing ever conceived by the human mind. Yes, they make your chest look good, and a good-fitting bra will keep you supported no matter what. However, ill-fitting bras will either ride up your back or hang off your chest, either way creating some undesired feelings.

a close up of a bra on a tableMalta Gordos on Unsplash

15. Bralettes

Similar to bras, bralettes also have the issue of not being super supportive. If you’re a smaller-chested person, they could be a great option, but anyone over a B cup knows they’re going to be hiking the ladies up time and time again.

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16. Tights/Stockings

They can look super cute when they're the proper size, but otherwise, they’re just plain annoying. Stockings have a tendency to run or catch, causing problems for anyone who needs to wear them for work, while too-loose tights will bunch around your ankles and start to sag around your pelvis. Too-tight tights make it difficult to sit, cross your legs, or just generally be comfortable.

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17. Teeny-Tiny Tees

The baby tee is an adorable fashion staple that goes well with just about anything, but that doesn’t mean they’re comfortable. The close-cropped nature of a tiny tee means you run the risk of bra exposure at the slightest lifting of your hands, leading you to continuously pull it down.

woman wearing gray and black striped long-sleeve shirt holding her wristAllef Vinicius on Unsplash

18. Underwear

Obviously, we need underwear to maintain decent hygiene, but can’t a company make them right? Certain types of underwear will bunch, leading you to have a diaper-like silhouette, while other brands have a thick band across the top that cuts into your waist. And don’t even get us started on thongs!

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19. Certain Hats

This one is a little more subjective, as different hats can look bad on different people, while a rare few folks don’t look great in any hat at all. Regardless, an ill-fitting hat will either leave you with a headache, a chic forehead line, or the constant need for readjustment.

a man in a coat and hat covering his faceAlexandra Tran on Unsplash

20. Bulky Coats

When the cold weather approacheth, we turn to our thicker coats. Unfortunately, the puffier the coat, the harder it is to move around in. It’s often cited as a bit embarrassing to have to try and tuck a backpack, tote bag, or purse over your shoulder when wearing one of these babies.

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