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How To Wear A Hoodie Over A Collared Dress Shirt

Wearing a hoodie with any formal wear is incredibly unconventional. But times are changing and fashion is evolving. So, can you really wear a hoodie over a collared dress shirt?

You can wear a hoodie over a collared dress shirt, but you must do so with caution. Make sure it’s appropriate, and keep patterns to a minimum. Consider wearing a zipped hoodie as they will leave the shirt collar visible.

While that’s the gist, there’s a lot more to it.

So, let’s get to it. 

shirt under hoodie
Image From Deposit Photos

1. Strongly Consider A Zipped Hoodie

Layering is common in both formal and casual apparel. However, layering the two together is something of a grey area in style.

That being said, doing it is still possible and can demonstrate your style prowess and confidence in experimenting.

A solid way to layer a hoodie with your dress shirt is by going with a zipped hoodie. 

While wearing an unzipped hoodie is still technically layering, a zipped one can really add some depth to the outfit.

Leave your hoodie partially zipped to show off your dress shirt underneath but maintain the hoodie’s centerpiece status.

Alternatively, leave your hoodie fully unzipped if you wish to show your daring experimentation.

This will make your dress shirt highly visible and is a fantastic fashion statement.

2. Hoodie Color Matters

The color of your hoodie is the first thing to think about. 

Because your hoodie is a primary piece of the outfit, and it will seem somewhat out of place with a dress shirt, it’s important to get its color right.

Doing so will minimize the prominence of the outfit’s formality mismatch, transforming it from a strict fashion faux pas to something that can look great.

Of all the colors, grey is arguably the best one for your hoodie when wearing it over the top of a dress shirt.

Grey is an incredibly versatile neutral color that pairs nicely with pretty much any other color.

Image From DepositPhotos

Moreover, if you pick a light grey hoodie (as opposed to a dark grey one), it’ll couple with the likely lighter tone of your dress shirt for a near-monochromatic look.

If grey isn’t for you, however, pretty much any color can work with this outfit, as long as it isn’t too loud.

Bold, bright, loud colors can interfere with the look, drawing too much attention to the hoodie and, thus, detracting from the rest of the outfit.

While this may be acceptable with some outfits, it’s generally best to avoid it with this outfit.

Not only will it detract from the rest of the outfit, but it will look even more out of place when worn with a dress shirt.

This is because, generally speaking, loud colors make statements, as do formality mismatches, such as wearing a hoodie and a dress shirt together.

Sometimes, you may be aiming for a statement outfit, and if this is the case, feel free to wear your hoodie and dress shirt however you like.

But if not, it’s best to avoid making two major statements together.

3. Tucked Vs. Untucked Dress Shirt

Knowing if you should wear your dress shirt tucked or untucked with an outfit as controversial as this one can be a huge challenge. 

Some may lean towards the “it’s casual, so leave your shirt untucked” approach, while others may go for “dress shirts should always be tucked.”

Both are valid statements and should be taken into consideration when making your final decision.

To be completely transparent, whether or not you wear your dress shirt tucked is entirely down to you.

However, here are a few factors to think about during your decision-making process.

Firstly, dress shirts are noticeably longer than casual shirts, as they’re designed to be tucked in.

They have a long and rounded hem that will most likely peek out beneath the hem of the hoodie. Technically, it’s a tell-tale sign that the shirt was meant to be tucked in. 

Not a great look. 

This specific design, as well as the formality of a dress shirt, are great reasons to leave the shirt tucked when wearing a hoodie. 

On the flip side, hoodies are very casual garments. Your hoodie will be considerably more visible than your dress shirt.

Some may argue that the additional length of a dress shirt could be seen as a stand-out feature – one that adds some flair to your outfit.

It’s up to you. But in general, it’s best to leave a dress shirt tucked under your hoodie. 

long oversized shirt under hoodie
Image From Deposit Photos

4. Ensure It’s Appropriate 

It’s no secret that this outfit is extremely controversial.

After all, dress shirts are worn at events demonstrating the epitome of formality, such as black-tie and white-tie events. 

Hoodies, on the other hand, are only usually worn on casual occasions. For example, you might throw on a hoodie to keep warm on a quick trip out to the shops.

This stark formality contrast means that this outfit isn’t suitable for every situation. 

In fact, it makes it inappropriate for any formal occasion, despite the dress shirt, leaving only informal scenarios.

On top of this, the casual nature of the hoodie overpowers pretty much any formality level of the dress shirt, meaning that it’s only appropriate on casual occasions.

So, to ensure you are never underdressed for your formal event, remember to avoid this outfit on occasions of even a slight bit of formality.

That being said, it’s important to make sure that your outfit works in the instance that, for example, you have to take your hoodie off.

Taking off your hoodie to reveal your dress shirt will completely change the dynamic of the outfit – making it considerably more formal.

To keep your outfit looking casual, even with a dress shirt, consider leaving it untucked, rolling up your sleeves, and unbuttoning the top one or two buttons.

Doing so will dress down the shirt as much as a dress shirt can be dressed down.

5. Try To Avoid Patterns

As mentioned, wearing a hoodie over a collared dress shirt is very much a statement outfit.

Because of this, it’s important not to go overboard in the other aspects of the garments, such as color, pattern, and extra detailing, like hoodie graphics.

Patterns are one of the things that it’s usually best to avoid with this outfit.

This includes hoodie, pants, and dress shirt patterns, as these are the most visible parts of your outfit.

As such, avoiding them will keep the formality contrast between your hoodie and dress shirt as the singular statement of the outfit.

Not going overboard is incredibly important (unless you’re trying to make a major fashion statement) because doing so will seem extravagant or flamboyant.

Some may argue that you’ll appear this way, regardless, when wearing a hoodie with a dress shirt.

However, if you do it the right way and follow the tips in this post, your statement will be visible yet subtle – showing experimentation yet respect for boundaries.

6. Think About Pants Style

The optimal pants style to wear with this outfit is an interesting topic. 

Do you match your pants’ formality with your dress shirt or your hoodie, or do you go somewhere in between?

Pants can generally be split into four distinct categories. These are utility, casual, semi-formal/smart-casual, and formal pants.

Utility pants are those that are designed to fulfill a particular task, such as joggers for running.

Their design isn’t usually too concerned with appearance, and they usually favor function over fashion.

Casual pants are those that thrive in casual scenarios and are usually inappropriate for formal or semi-formal events.

Cargo pants and light-wash or distressed jeans are fantastic examples of casual pants.

As we move up the ladder to semi-formal/smart-casual pants, examples include chinos and dark blue or black jeans (with no wash nor distressing).

Finally, the formal pants category is pretty much solely dress pants.

The best pants category for this outfit is on the more casual side of semi-formal/smart-casual.

What this means is going for chinos or dark blue or black jeans, but those with some informal features.

For example, if you go with chinos, consider wearing those of a more casual color – avoiding colors like charcoal, navy, and black.

Similarly, dark blue or black jeans can look great, but think about going for distressing or a lighter wash, as these features wouldn’t usually be seen formally.

Doing this will ensure your pants match both your hoodie and your dress shirt, so if you have to take your hoodie off, your outfit still appears intentional.