Pressed & Proper Blog

If you’re like most men, you make a million little decisions each day. You pair your socks with your shoes. You pair your toast with jelly…or should it be butter today? You agonize over which tie to wear to work, and wonder if you should start parting your hair the other way.

And that’s all before you even get to work.

If you’re feeling sick and tired of all of the “decision fatigue,” don’t fret. It’s simply a symptom of all of the little choices you've been making day in and day out. Luckily, there are ways to cut down on decision fatigue, especially when it comes to your wardrobe. Pairing a shirt with a trouser shouldn't be an agonizing decision, after all; it should be something that comes natural. And if it doesn't? Well, then you've got this handy guide to steer you in the right direction.

It might not seem like a necessity at first. Most men don’t grow up learning how to match their shoes with their pants, so they think any old pair of shoes will tend to go with any old pair of pants. As an adult, you know that clothes aren't so simple. You have responsibilities now—not only to look good at the office but to come off as a presentable individual in any new situation. Whether you're dressing for an important meeting or going on a first date, you'll want to look your best. “Big deal,” you might say. “So I’m wearing black shoes and brown pants. Who notices that sort of thing?”

The truth is, being a conscious and well-dressed man means that you should notice that sort of thing. Luckily, understanding how best to match your pants and shoes isn't not rocket science. Here's what you need to know.

It’s the unmistakable sign of a middling fashion sense: clothes that don’t quite fit. Even if you think you’re buying the right pants, the right suits, and the right button-downs, you’d be surprised at how disheveled your look can be until you’ve corrected perhaps the most fundamental aspect of what makes good clothing look good when actually worn: proper fit.

Of course, if you’re only a casual sartorial enthusiast, it’s not always easy to tell when your clothes fit and when they don’t; you just know what feels comfortable. That’s why we’ve put together these tell-tale signs that your trousers are in need of a good tailoring:

It might seem strange to recommend a pair of shorts for almost any occasion. True, for some occasions, only pants will do. Weddings, funerals, and many Sunday church services. But for the rest of the world you encounter this summer on a hot day, there can only be once choice: shorts are the only way to look good while staying remotely comfortable.

But comfort never trumps fashion; you have to find a happy medium in which you’re comfortable and you’re occasion-appropriate. That’s especially true for the more formal occasions and responsibilities you’ll face this summer that require a bit of dressing up.

So which shorts fit which situations? Let’s take a look at some of the shorts at Berle and see which ones might suit you best in differing circumstances:

The word “summer” might mean “vacation” for some, but there are no vacations from style. True: in summer, most guys can get away with donning a pair of shorts, a polo, a nice pair of shoes, and call it a day. We can cut our hair short to stay cool, put on the occasional hat, and rest easy knowing that we look about as good as we feel.

The problem? You don’t want to be most guys.

“Fit, fit, fit.”

In the fashion world, “fit, fit, fit,” is what “location, location, location” is to real estate. In other words, if your clothes don’t fit you well, you can forget about any pretense of style you might have had—it’s just not going to look good.

This isn’t a reason to feel distressed about your wardrobe, however. Understanding whether your clothes fit you or not is more science than art, and once you develop a discerning eye for trousers that fit, you’ll never have to worry again whether or not your clothes are “hugging” you the way they should.

When it comes to clothes, we get it, guys: you don’t want to spend an arm and a leg simply finding clothing that will cover your arms and your legs.

But if you've shied away from any word like “tailored” or “hemmed” in the past simply because you assumed that such a process would be uncomfortable, or prolonged, or prohibitively expensive, or somehow make your clothes too tight—let us put those fears to rest.

Summer’s on its way, which means that people will be heading outdoors, looking for more sun, and showing more skin—both the men and the women. For you men, that means you’re going to be showing more skin, too, unless you want to inordinately sweat during casual get-togethers or family functions.

So how do you maintain your sense of style when you switch from pants to shorts? Heck, how do you develop a sense of style when it comes to wearing shorts? After all, if there’s one thing many men do wrong with their wardrobe, it’s incorrectly pairing shorts with clothing articles that have no business in your casual summerwear.

To solve these conundrums, let’s take a look at some of the most common concerns and questions men have when it comes to shorts:

Winter’s about to leave, and that means spring’s ready to make its merry way into our weekends, weeknights—heck, our whole lives.

Make sure your wardrobe changes accordingly.

This means more than simply swapping out a long-sleeve shirt for a short-sleeve shirt. It means more than switching from pants to shorts. When spring comes, it’s time to look at a change in fabric as well.

It’s not just about changing the style. It’s about changing the way you feel, maximizing the comfort you get out of your spring and summer. And in order to do that, it’s time to leave the wools at home and embrace a different kind of fabric weave that will have you feeling and looking your best this season: seersucker.

Shorts. They’re perhaps the most simple item in your wardrobe—often a monochromatic, singular piece of fabric that’s designed for maximum freedom and minimal utility. So it’s difficult to imagine them as a fashion statement, a way to break out of the mold and call a little attention to your sartorial good sense.

Difficult to imagine, that is, until you meet patch madras shorts.

These lively, original patterns have a distinctive, preppy appearance to them without ever looking disheveled. In essence, they’re a perfect way to spice up your spring/summer wardrobe—and since you can pair them with a good polo shirt, button down, and more, they’re also surprisingly versatile.

Convinced you should add a pair to your wardrobe? Good. Now let’s explore all of the options you have for creating both dressy and casual outfits.

Yes, men, it is possible to wear walking shorts and look every bit as stylish as you do on those days of long pants and blazers.

But not many men know this, which has led to an altogether lack of optimum walking shorts attire. You’ll see vacationers donning khaki shorts with sneakers and white athletic socks. Or maybe you’ll make the mistake of bringing a casual pair of khaki shorts to a tennis match when what you really need are some performance shorts.

How do you know which walking shorts are appropriate to which situation—and what to wear with them? By keeping yourself together with just a few of our walking shorts tips.