Just like dress trousers that fit well can make you look more professional; casual pants can communicate laid-back confidence and the sense that you know what you’re doing. There are a lot of different types of casual pants, so for this article we’ll focus on the majors: chinos, jeans, shorts, and we’ll through in one more. For no reason at all, let’s start with the preppiest.
Casual, but not like you’re ready to go lumberjacking. This is more the, “I’m going to grab coffee with a few friends and then go to the park” sort of casual. Similar to dress trousers, chinos should fit slim, but not tight. Chinos are more active than dress pants, so you’ll want to be able to move around in them. Fortunately, the cotton tends to be a little lighter weight, so it should be able to move with you more easily. As always, you want to make sure that the fit is flattering. Current trend is to have the waist sit at your hipbones.  The best fit for most guys is to fit close to your leg the whole way down. Try a slim fit that tapers in the leg. If you’re looking for an exact measurement on the leg width or leg opening, then you’re thinking too hard about this. These are casual pants, so take it easy for a minute. Just try them on with a good pair of sneakers The pants should rest high enough on the shoes that you’re not hiding them, and make sure that they never drag the ground. If they are too long you can hem them, or just roll them up.
Jeans are all about leg protection. They are tough and thick, and unless they are blended with some other material, they are pretty inflexible. For this reason, you can wear jeans a little looser than chinos. But, don’t forget that you are still looking for slim lines and a flattering fit. Jeans are such a staple that it can be hard to stand out when wearing them, so many guys tend to dress up too much for the environment, or more common, just decide not to care.
How can you look great and stand out in a world covered in denim? Fix the fit!
If the pants say Baggy or Loose, you’re going to have something far to big on your hands. These are going to hang very loosely on your body, and are more fit for the street scene than for creating casual confidence. Look for straight or slim straight cuts. These will hug closely to your thigh, and run smoothly down your calf. The slim straight will taper from the knee down to hug your leg a little more closely. This is a trendier look, but still classic enough to look great.
Shorts come in all shapes and sizes, so I’ll just give you the simple version here. You’re trying to look like an adult. Baggy cargos, and jean shorts with large graphic elements aren’t doing you any favors here. When you’re picking shorts look for something that ends between 3/4 down your thigh above your knee. If you tend to dress preppier (polos and khaki shorts) err towards the higher side, and if you’re the kind of guy that goes surfing on the weekends, go a little longer. You want your shorts to fit like a good pair of chinos or maybe just a smidge looser. Avoid shorts that end past your knee. This was a street and skate look from years ago that shortens your legs in an unfavorable way. These shorts are oversized, and just don’t fit.
Extra: Linen for your beach trip
I can’t wait for summer because then I can finally wear my white linen pants. I originally bought them for a company “white party”, but they have become a staple of my wardrobe in the summer when I’m at the beach or just want to relax. Linen is breathable, and it flows very nicely when it’s loose.
So this means that I am finally recommending a baggy fit! Linen pants should flow as you move. Wrinkling, draping and bunching is fine. You still want them to make you look better; so make sure you get the correct waist size. If you have a bit of a stomach, get a pair with a non-elastic waist. The elastic will always pull against your stomach causing spillage that you don’t want.
Also, pay special attention to the length of your pants, especially if they are white.
Dragging the hem of your pants on the ground is not a good look – white pants with a mud-brown hem? No.
If they do run too long you can again take advantage of the casual nature of these pants. Roll them up! Rolled pants with a pair of sandals is a chill summer look.
Now take a close look at what you’re wearing on casual days. Who are you presenting to the world when you’re just hanging out? Causual environments don’t mean anything goes. If you pay attention to the fit of your “chill” clothes, you’ll look effortlessly cool all the time.
- This will extend your torso visually, so keep this in mind. If you have shorter legs, go for a slightly higher waist and a higher rise in the crotch. ↩
- slim fit cargos are trending right now, but they won’t be in a couple years. Unless you’re hiking, just let this one pass. ↩
- A beach party where everyone wears all white. ↩