What to Wear With Each Pair of Trousers

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.

Dark Tailored Trousers

Sweaters, tucked-in button downs, button-downs and button-ups with blazers. This is generally a “business casual” look. When you’re wearing dark tailored trousers, you generally mean business; lighter and less formal trousers are better for more casual faire.

Light Tailored Trousers

Button-downs, polo shirts, dark-colored sweaters (for contrast). What if you’re wearing something like these Super 100s Gabardine Flat Front trousers? Your options become pretty limitless. But if you’re steering in the direction of business casual, you’ll want to keep the rest of the outfit generally on the same page. A t-shirt need not apply here.


Casual Pants

Button-ups, polos, and even casual tees. Yes, you can wear blazers with casual pants like chinos, but it becomes more important to properly match colors and fabrics if that’s the case. It gets a little complicated. We like sticking to a more business casual or even casual look.

Charleston Khakis

Blazers, sport coats, sweaters, button-downs. The Charleston Khakis you see here are incredibly versatile, it’s true, but we think the best fits tend to be these wardrobe classics. You can dress them up easily with a sharp blazer or keep them a little more casual with a sweater or button-down. Or you can layer them together for a sharp, smart look.


Button-ups, polos, tees. Consider shorts a type of casual pant—a very casual pant at that. True, shorts are a little more casual than the casual pant recommendations we made just a few short paragraphs ago, but that doesn't mean that shorts can’t be elevated to complete a smart outfit.

Pleated Dress Pants

Pleated dress pants belong with ties, which means that you’ll want to wear button-downs with them as well as a suit-coat if necessary. Yes, you can get away with the “tie, no jacket” look, but generally pleated dress pants look best when paired with the complete ensemble.

Are these hard-and-fast rules? Not necessarily. Any sartorial enthusiast knows that you can break the rules if you know what you’re doing. But these pairings will help you look your best and reduce your “decision” fatigue. Now, if only you could decide which pair of shoes to wear…