What to Wear With Your Trousers in Any Situation

So you’ve mastered the art of trousers. Congratulations. Maybe you’ve read some of our previous posts like matching socks with trousers or dressing in the summertime. Great! You’re on the path to sartorial brilliance.

Of course, when it comes to the area outside of the trousers, it can sometimes get a little more complicated.

We at Berle like to focus on the art of the trouser, of course, but we also acknowledge that trousers don’t live in a vacuum. Eventually, you’ll have to look in your closet and decide to pair those trousers with something, and that “something” will vary, depending on the situations in which you find yourself.


The Wedding Guest

You’re a wedding guest - not a groomsman, but merely a guest. Since most weddings tend to be formal, you’ll want to wear a button-down shirt with at least a tie or a blazer. Tuck the shirt in, add a pocket square to match, make sure the belt and shoes match color, and you’ll be good to go.

Some weddings aren’t so formal, however. You can always dial down the formality by taking off the outer layers: remove the blazer and go tieless, and maybe undo that top button or roll up your shirt sleeves.

The Job Interview

Job interviews can be tricky. On one hand, you want to make the best impression possible. On the other, the interviewers might tell you to dress casually. What do you do?

We recommend pairing a nice pair of flat front trousers with a button-down shirt. As was the case in the “wedding guest” section, you can then add a layer as the formality increases. A sport coat and tie will maximize the formality; having one or the other will keep it more casual.

The First Date

There are plenty of options here, and that’s a good thing: because there are plenty of different first dates as well. We recommend staying stylish but casual: a polo shirt on top of a pair of khakis is conservative enough for most first-date situations. If the temperature is cooler, you can also add a layer like a v-neck sweater over a collared shirt or a plain white tee (depending on how formal you want to look).

Principles of Pairing Trousers and Shirts

Generally, you’ll want to pick complementary colors when it comes to pairing trousers and shirts, no matter what the situation. Yes, you can get away with an all-white pairing on a hot summer’s day...but it gets a little trickier after that. You’ll find that white trousers provide plenty of versatility, as do white shirts. Blues and reds frequently go together, and browns for the shoes and the belts are incredibly versatile.

As for picking the type of shirt to wear: it takes practice. But try to think of things in layers. Starting with a plain white tee is a casual base; but you can add to it with a sweater on top. A button-down shirt gives you a more formal base, and you can add jackets and ties to increase that formality.

Generally, for most situations, you’re best off finding somewhere in the middle. But for those special occasions, make sure to give a thought to everything you wear on top - even if you’ve already mastered the “pants” section of your wardrobe.