Should You Wear Socks with Shorts and Other Fashion Advice

Once again, we're moving into the warm months. Shorts season is here, and many of us are ready to get out in the sun and enjoy all that summer has to bring. Before you slap on your shorts and run out the door, you need to stop and check your fashion sense. A lot of guys struggle with fashion, and they particularly struggle with shorts. It may surprise you to learn this, but the vast majority of shorts fashion faux pas stem from misunderstanding socks. We're going to break down this segment of fashion. When you're done reading, you'll be an expert in socks, shorts, and how to look great when the days are long and hot.

A General Rule to Get You Started

Fashion is a complicated topic, if we're honest. Just like people often ask us, "satchel vs. purse?", men also inquire about the rules of socks with their shorts. You can get by with a few hard and fast rules, but you find that things get convoluted as you dive deeper. So, before we get into those deeper details, we're going to start you with some general advice regarding your shorts and socks. The idea goes like this: socks should not be seen when you wear shorts; this is a rule passed down to us by the elite aestheticists, and sometimes, we should simply trust them.

We can extend this rule a little further. Socks shouldn't be seen at all. When you wear pants, you can have long socks because the pants cover them, but the rule with slacks is that the socks should not be obvious when they peek out from under the pants. There's nothing to hide the socks with shorts, so you have to pick socks that won't show.

So, if you're wearing shoes, you still want socks. Going sockless with closed shoes is a whole mess of problems that none of us need. That said, your go-to for socks and shorts should be no-show socks. They're super common. You can find them anywhere. They're designed to come just to the top of the shoe, so you get the protection and odor barrier that socks are designed to provide, but you don't risk crossing the aestheticist overlords. No-show socks are a safe bet, and they're a great way to approach shorts season.

Then again, shorts season and sandals season perfectly overlap. You might be wearing sandals with your shorts. That's perfectly normal, and it's a great look in many scenarios. The rule here couldn't be simpler. Don't wear socks with your sandals. It adheres to our general rule, and it's probably one of the few rules of fashion you've heard ad nauseam. If you stop here, you'll stay out of trouble, and you'll be fine. If you can't resist knowledge, adventure, or the hope that what comes next can alleviate a little boredom, then keep going down the rabbit hole. Just understand that the rules stop being reliable after this point.

The Exceptions That Blow up the Rule

They say every rule has an exception. Socks have a bunch of exceptions. They're not supposed to be seen, except when they are. Acceptable visibility in socks is almost completely arbitrary. The rules change fast and unpredictably. Guys shun socks until they see someone pull off a surprisingly enjoyable look. No one really gets it, but it happens, and we're going to layout the current trends.

Before we do, there's a final disclaimer. These looks are acceptable now. They will eventually fall out of fashion. These are looks that your children will ridicule. But it'll be ok because they'll probably be caught up in their own fad of the day or week or whatever.

The Sporty Look

So, this might be a little surprising, but it turns out that you can sometimes get away with tube socks or athletic socks while you're wearing shorts. The trick is to make sure they match your shoes; this doesn't mean they have to be the same color as your shoes. That normally looks pretty weird. The point is that they can't clash with your shoes.

If you're going to do this, you're looking for a fashionable, sporty look. You want those socks all the way up with no scrunching (which means socks with loose elastic are out). They should come to the midpoint of your calves, and that's part of the look. The calf-high socks can accentuate the shape of your leg and actually look good. That means, of course, that you should only consider this style if your legs are in good shape. You have to have defined calves to make this work—no shame to those of you a little behind on leg workouts. Just put in the time before you try to rock tube socks with shorts.

Going Pastel

The other big exception to the rule is using pastel socks. Once again, they can't clash with your shoes. Also, you can't do this with athletic shoes. You need to be wearing something nice on your feet. That also means you can't be sporting gym or cargo shorts with this style. Chinos are the in look right now, but whatever you wear, it should probably resemble stylish slacks that happen to stop at the knee. With your pastel socks, you have a few options. You can wear them up like tube socks (still coming to mid-calf). You can also bunch them a little to make them look a little more casual. If you do bunch them, don't go too hard. They shouldn't bunch by more than an inch. You don't want an awkward pile of socks at your ankles. That defeats the purpose.

Boldly Going Beyond

The last exception is a lesson in fashion altogether. Sometimes, a bold rejection of the rules is amazing. That said, any time you take this route, you're playing a high-risk game. Your bold look might fall flat, and because it's bold, everyone will notice and comment. If it does work, you get the high rewards that come with the risk.

When we're talking about socks, you can wear some attention-getting socks with your shorts. It becomes a daring practice of expression and confidence. Your socks can be a conversation piece, an ice breaker, and honestly, the funny way you made a new friend. If you want to get the most out of your bold socks, you have to highlight them. Tone down the rest of your outfit and let the socks do the talking.

Bold Fashion Can't Be Faked

It's important to understand that bold fashion can't be faked. You have to walk with real confidence to pull off a bold look (and it doesn't hurt to be wearing the best men's underwear when you're doing it). Fake it till you make it is best left for other endeavors.