How to know He’s still a boy

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15 Things He Wears That Show He’s Still A Boy (& 5 That He’s a Real Man)

Even if they’re not exactly Miranda Priestly from The Devil Wears Prada when it comes to fashion, most girls can admit that they like looking good when they go on a date. Ladies want their hair and makeup and outfit to be beautiful, and it matters to them that they make a good impression.

When they start dating a new guy, one of the first things that girls notice is that while they try not to wear the same thing all the time and rotate their outfits, he’s not doing the same. He’s wearing the same t-shirt, jeans, and hoodie pretty much on every date that the two go on. Sure, he might have an adorable sense of style, but there are definitely a few girlfriends or wives who wish that their guy would try a bit harder when it comes to getting dressed.

There are some outfits that are better than others and some items of clothing that suggest that someone might be a little bit immature. Likewise, there are things that impress the ladies and show that a guy has a great sense of style. Here are 15 things he wears that tells his date he’s still a boy (and five that he’s a real man).

20 Boy: Ripped Jeans (But Not On Purpose)

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Ripped jeans are a staple in many people’s wardrobes. Whether a pair of jeans has some tiny and creatively placed rips throughout each leg or a huge rip in one or both knees, these are easy to pair with many different tops.

We’ll know that he’s a boy if he wears jeans that are ripped… but not on purpose. 

Many of us would agree that ripped jeans are only cool and stylish if they are bought that way. If a guy is wearing jeans that are so old or in such disrepair that they’re all ripped up, it’s a fashion don’t and also might speak to his immaturity. We would definitely want to ask him why he doesn’t go out and replace his jeans.

19 Boy: Band T-Shirts

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Band t-shirts are a popular item of clothing for high school and also college/university-aged boys. They go to concerts on a regular basis and love buying these. They also like getting them for super cheap at a vintage or thrift store.

We get it for sure… but we do have to say that if someone is above a certain age and still wearing their old band t-shirts, it might be time to buy some new shirts. There’s nothing wrong with band t-shirts per se… it’s just that they aren’t as mature and sophisticated as a plain white, grey, or black t-shirt.

18 Boy: T-Shirts He’s Had Since High School

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On that note, if a guy is still wearing the t-shirts that he wore in high school and now he’s in his mid-twenties, that’s not the best sign and we could say that he’s still a boy.

Clothing, like food, is a powerful and nostalgic thing.

Many people find it tough to part with the items that they used to wear. That’s why so many people don’t give away or throw out clothes that no longer fit them. But a t-shirt that is super old might have holes in it and the color might be super faded. T-shirts are fairly easy to find at many different clothing stores, so we would wonder why he hasn’t replaced his shirts and why he’s still wearing the same ones.

17 Real Man: Dress Shoes

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If a guy is wearing dress shoes, we’re definitely going to say that he looks like a real man. This is a truly impressive type of shoe.

Dress shoes say maturity and sophistication and elegance. They tell us that this guy knows how to look fashionable, and he’s probably paired them with some seriously stylish ensembles. Think a suit, a blazer, and nice dark jeans, or a clean-cut t-shirt with a pair of dress pants. We would look at him and wonder what he does for a living and think that he’s got an amazing work ethic. The clothes might make the man but the dress shoes will make the man, too.

16 Boy: Sweatpants

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What can we say about sweatpants? Well, we can say that anyone wearing them might not be the most mature person ever. Okay, we should note that we get that wearing sweatpants while at home is a nice, cozy thing. We would never say that there’s something wrong with that.

The problem with sweatpants is when people wear them outside and in public.

They’re not the best thing to wear to school or work or out to dinner, and if we went on a first date with a guy who wore sweatpants, we would wonder why he didn’t put any more effort into choosing what he was going to wear.

15 Boy: Socks With Holes In Them Or Crazy Patterned Socks

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Finding plain socks isn’t very hard. You can get them from pretty much any store, either in the actual store or online, and you can find tons of deals as well.

If he’s wearing socks that have holes in them, it’s kind of weird (not to mention a bit gross). We would wonder why he hasn’t replaced them and why he doesn’t take a bit more pride in himself. Wearing nice socks is just a normal thing to do, right? And if he’s wearing colorful socks with a really silly pattern on them, we might wonder why as well. It’s not the best look when someone is of a certain age.

14 Real Man: Brown Or Black Blazer

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A real man wears blazers because he knows that they are gorgeous and instantly elevate any outfit. If we think about our own closet and sense of style, we know that there’s a huge difference between wearing a dress with a blazer and wearing it with a jean jacket or sweater. It just makes the entire outfit sing.

Whether he’s wearing his blazer with dress pants or jeans, or his jeans are perfectly ripped (on purpose, of course) or fancier than that, we’re going to call a blazer a fashion do.

It is something that always looks awesome, and we can all agree with that.

13 Boy: Oversized Hoodie That Doesn’t Fit At All/Wears The Hood A Lot

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Hoodies are a tough item of clothing. They have to fit perfectly if they’re going to look good, and they have to be a good color, too. A neon-colored hoodie, for example, is anything but stylish, but a nice black or grey one might look good on the right guy.

If he’s wearing an old hoodie that is super baggy or he wears the hood up a lot, that’s another story, and it’s not a fashionable one. Oversized hoodies that don’t fit aren’t very attractive. They don’t look cool and he should replace them with one that is actually the right size (or a tiny bit looser).

12 Boy: Flip-Flops

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Unless you’re on vacation, flip-flops aren’t something that should be worn on a regular basis.

They would suggest that the person wearing them is still a boy since he doesn’t have any proper, real shoes.

The problem with flip-flops is that they are way too casual for almost any event, place, or situation. They aren’t out of place at a pool or beach, but chances are, the guy wearing them is walking around his city or he’s heading to dinner with friends or family or going on a date. He should get some real shoes, right? Yes, he should for sure.

11 Boy: Old Sneakers That He Hasn’t Replaced

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Old, gross sneakers that badly need to be replaced aren’t the most attractive footwear, either. If we went on a first date with a guy who was wearing super old-looking sneakers, we would have a lot of questions.

First of all, he would wonder why he didn’t just go out and buy some new shoes. There are so many deals everywhere these days, especially if you do some online shopping, and it seems like it would definitely be possible to get at least one new pair of sneakers. Second of all, we would wonder why he didn’t want to wear better-looking shoes.

10 Real Man: Collared Shirt

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A real man wears a collared shirt to work, to formal and more casual parties and events alike, and whenever he feels that it’s a good idea.

The thing about a nice shirt is that it can be dressed up or down.

He can wear one with nice blue or black jeans or with dressier pants. He can wear it buttoned up all the way if he’s going for a formal look and heading to a work event, or he can roll his sleeves up if heading on a date or to a fun party with friends. It’s a really cool look either way, and we’re going to think that this guy is so stylish.

9 Boy: A Backwards Baseball Cap

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A backward baseball cap is a super immature look. Sure, we get that people think that wearing a backward baseball cap makes them look cool, but we think that it makes them look much younger than they actually are.

Guys can get away with this in high school but once they graduate and enter the working world, we would probably all agree that it might be time to retire this particular hat look. If they want to wear a hat, then by all means, wear a hat, but wear it facing the right way (that’s the best way to get some sun protection, too).

8 Boy: A Windbreaker

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He’s still a boy if he wears a windbreaker because this is something that kids wear when it’s raining or a little bit cold out (think spring weather). It doesn’t seem like the best thing to wear when someone has graduated from high school or college and is trying to seem like a grown-up.

The problem with windbreakers is that many of us would agree that they’re not always that fashion-forward.

Some have a weird combination of bright colors or patterns or just aren’t the most flattering shade. These jackets also make someone’s overall outfit look sporty, and that might not appeal to everyone.

7 Real Man: Nice Jeans That Aren’t Ripped

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A real man wears a nice pair of jeans that aren’t ripped at all. That goes for tasteful jeans that are sold already ripped, too.

These jeans can be any number of shades, from dark denim to black to light blue. They are all attractive and we would immediately think that any guy wearing a nice pair of jeans was trendy and really knew how to dress. He at least knows the importance of buying a nice pair of jeans and he wouldn’t want to leave the house in a piece of clothing that looked old and tired and ripped, and we can appreciate that.

6 Boy: A Puffy Vest Instead Of A Jacket In The Winter

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There is something about young guys that makes them think that wearing a winter coat or jacket is a truly bad idea. If we think back to our high school or college days, we can probably remember a friend, boyfriend, or our brother wearing a puffy vest instead of a winter coat.

This is not only unfashionable but it’s also pretty silly since come on, winter is a cold time of year. That’s the whole point.

A guy wearing a vest instead of a real, actual coat isn’t going to impress his friends or a girl. If we see this, we’re just going to think that he looks freezing and wonder what happened to his coat.

5 Boy: Board Shorts

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Board shorts say boy, not man for sure. They’re probably fine on a tropical or toasty beach vacation because, hey, everyone has loosened up the reins a bit when it comes to clothing and people are wearing much more casual outfits than they would normally.

But if someone wears board shorts out and about in their own city or town or, worse, wears them on a first date or to an important party or event, it’s game over. That’s not the best idea, and we would wonder why they hadn’t gone for something at least a little bit more fashionable.

4 Boy: Polo Shirt

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Are we getting high school flashbacks?! When many people think about polo shirts, they remember all the boys in their high school class wearing these on warm days or to pool parties on summer weekends.

The polo shirt may be preppy but at this point, it kind of feels like it’s gone out of style.

And the polo shirt might be something that many people think signals class and power, but honestly, it’s often paired with shorts or jeans and flip-flops, and the whole look is kind of childish. There are many more items of clothing that are more mature and sophisticated.

3 Boy: Turtleneck Or Sweater Over Another Shirt

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Turtlenecks may keep you warm in the winter but why not just grab a scarf and wear that? When a guy wears turtlenecks, it makes him look a lot younger than he actually is, and that might not be the look that he’s going for.

The same thing is true if he wears a sweater over another shirt. This is a classic outfit combination but definitely screams “high school” and would make him seem like more of a boy than a man. We would suggest just picking out a nice sweater and that any guy should forget wearing a shirt underneath it.

2 Boy: The One Plaid Shirt He Owns

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Look, we have nothing against plaid. We love wearing plaid shirts and leggings and cozy socks on a fall or winter day, and plaid can be a really cute pattern for other things like sweaters and dresses.

If a guy only owns one plaid shirt and wears it over and over again, it might not be the most stylish thing ever.

The thing about plaid shirts is that they can contribute to a certain look (aka lumberjack), especially if paired with jeans and a beanie and work-style boots. It appeals to some people but not everyone, so it just depends what your type is.

1 Real Man: A Tie

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Of all the things that a guy can wear on a daily basis, a tie might not be one of them, unless he’s a lawyer or has to dress in formal wear for his job. But even if he has a more casual job than that, he might wear this to weddings and other special events.

If he’s wearing a tie, we could definitely consider him a real man. He’s probably wearing it with a nice shirt, blazer, dress pants, and dress shoes, and it’s going to be a really fashionable and attractive look (we won’t judge if he has to Google or look up how to tie a tie on YouTube, though, although he might keep that a secret from us).