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How To Wear High (Long) Socks With Shorts

High or long socks have existed for a long time; however, recently, in particular, they have exploded in popularity.  So, can you wear high socks with shorts?

It’s entirely possible to wear high socks with shorts. Consider the color of your socks – neutral colors work best – and think about the style of your shorts. Avoid dress socks, and remember that sock branding can look great.

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

So, let’s explore the topic further.

1. Consider Sock Color

Sock color is one of the most important factors to consider when wearing long socks with shorts, as the entirety of the socks will be visible.

Since the socks will be the centerpiece of the outfit, it’s important to get the sock color just right.

While it can be confusing to know the best color to match with your other garments, there are some colors that pair seamlessly with pretty much anything.

For example, black and white are both neutral colors and are, therefore, incredibly versatile. 

Image From Deposit Photos

A neutral color is one that doesn’t appear on the color wheel. Often, neutral colors pair easily with many colors because of this.

Not only that, but white is the lightest color and black the darkest, meaning that there’s a lot of room for different shades of colors to be worn with them.

It also means that you can easily add contrast to your outfit without it seeming excessive or over the top.

Other neutral colors that work well as long socks with shorts include navy, off-white, and shades of grey.

Some colors can be worn seasonally, too, because some colors are more appropriate in particular seasons than others.

For example, if you want to wear shorts in the fall, but it’s somewhat chilly, high socks are a great option for warmth and allow you to pick seasonal colors. 

Olive green, for example, is a fantastic choice to wear with shorts in the fall.

2. Keep It Casual

Getting the outfit right for the formality of an occasion can be tough. 

Not only this, but it’s also essential, as getting it wrong could be seen as disrespectful. 

This can put a lot of pressure on you to know the standards for particular dress codes.

When wearing high socks with shorts, it’s important to remember to keep it casual.

That is to say; this outfit is only appropriate for casual scenarios. 

Dress socks are often longer, which could lead some to believe that this outfit is best kept for formal situations. This is not the case.

Shorts are inherently casual garments and should always be worn as such – with only a couple of exceptions (such as smart-casual weddings in hot weather).

And while some may argue that longer socks are formal, there are many instances – such as athletic tube socks – where longer socks are considerably more casual.

Therefore, when wearing high socks alongside shorts, it’s crucial that you remember to keep it casual.

shorts and crew socks
Image From Deposit Photos

Keep in mind that if you ever think it might not be appropriate, then it probably isn’t. So, if you’re unsure, it’s best to steer clear of it altogether.

3. Think About Shorts Style

Shorts style is another important thing to consider with high socks and shorts.

There are many shorts styles out there; some look good with this outfit, while others don’t.

Because of this, it can be difficult to know what shorts to wear and when to wear them.

Despite there being many styles of shorts, they can be split up into a few umbrella terms:

  • Sports
  • Board
  • Denim
  • Chino
  • Bermuda
  • Khaki
  • Cargo

Sports and board shorts are, by far, the most casual shorts styles and are rarely appropriate for going out and about.

Denim is the epitome of casual wear, making denim shorts ideal for this combination.

Chino shorts are slightly dressier but still pretty casual, so they are also great alongside long socks.

khaki shorts
Image From Deposit Photos

While it may seem unlikely, cargo shorts look fantastic with high socks, so long as the cargo shorts aren’t too long; they create a ‘streetwear’ aesthetic.

Bermuda shorts are the most formal shorts and are too long and formal to be worn with high socks, as a general rule.

The optimal casualness sits around mid-casual shorts, such as the aforementioned denim and chino shorts.

Board and sport shorts, being incredibly casual, aren’t appropriate for this outfit and should be kept for summer and sporting endeavors, respectively.

Furthermore, these kinds of shorts – especially board shorts – are best worn without any visible socks, meaning that wearing them with high socks is counterintuitive.

4. Sock Branding Looks Great

Sock branding is a subtle yet great way to add some personality and flair to your long-socks-with-shorts outfit.

Branding shows the style you’re aiming for because different brands are associated with their own unique styles.

Go for branding of a color that is either analogous or contrasting with the base sock color and ensure that it’s clearly visible.

For a more put-together appearance, match the branding of your socks with that of your shoes.

Wearing matching long Nike socks and Nike sneakers, for example, creates an understated harmony between the garments.

While Nike works well, it doesn’t necessarily have to be such a high-end brand.

Other brands, such as Adidas, Converse, and Reebok, have the same streetwear aesthetic.

5. Avoid Dress Socks

Many dress socks are long enough to be considered “long” or “high” socks. In fact, it’s pretty much become the norm for dress socks to be particularly long.

Even though dress socks are a style rather than a length, the term “dress socks” generally conjures up an image of long socks.

Because of this, when wearing high socks with shorts, it’s easy to assume that you should go for dress socks. This simply isn’t the case. 

Optimal high socks to wear with shorts are actually quite the opposite of dress socks; they are athletic tube socks.

The main difference between long dress socks and tube socks is the material from which they are made – dress socks are made from higher-quality materials.

This means that they have minimal texture, are often block-colored, and usually have no branding.

Tube socks, on the other hand, have an obvious texture to them and commonly have a stripe or two around the top of them.

These factors make athletic tube socks dramatically more casual than long dress socks.

Wearing high socks with shorts is very casual – as has already been established – so it’s best to avoid the more formal dress sock and stick to athletic tube socks.

6. Shorts Length Matters

While it may not seem important at first, getting the right shorts length is essential to pulling this outfit off.

Going with shorts of the wrong length can look clumsy and feel uncomfortable.

Shorts that are too short can look outdated, whereas shorts of excessive length can appear sloppy.

On top of this, if your shorts are too long, there can be some overlap between your shorts and long socks. This should always be avoided.

This means that, overall, the best shorts length is achieved when the ends of your shorts sit just above your knees.

If you wish to wear certain shorts, but they are too long, consider taking them to a tailor.

A tailor can hem your shorts, and while tailors can be costly, usually, it’s relatively inexpensive for a small job such as hemming.

7. Go For Casual Shoes

There are so many different shoe styles that it can be challenging to know which ones are best for your outfit.

Luckily, with this outfit, knowing the best shoes to wear is straightforward.

Because wearing high socks with shorts is so casual, it only makes sense for your shoes to be similarly casual.

This means avoiding dress shoes, such as Oxfords or Derbys, and going for sneakers or trainers instead. Tennis shoes can also look great.

Additionally, while some boots are casual, such as Chelsea boots, it’s best to avoid boots altogether when wearing shorts.

It may work for some, but as a rule of thumb, boots simply look out of place with long socks and shorts.