Pants

I almost didn't include pants on 31 Days of because it's so hard to know if a pant is good for you until you try it on. There are just so many possible pitfalls in pant sizing, but here's an easy rule of thumb: If you look uncomfortable in your pants they're too slim, and if you look too comfortable in your pants they're too large.

Life's too short not to have pants that fit well, and if you want to try a new style or cut, there's nothing wrong with buying an inexpensive pair from Uniqlo or the Gap or somewhere else to get a sense of if you like it. In the end, if it was a bust, you didn't lose too much of your investment, and if it's perfect, then you know it's worth it to buy a nicer pair.

1. Earl’s Apparel Gung Ho Expedition Pant

Earl's Apparel pants are the exact opposite of slim fitting. They are roomy, durable, and very cheap for a USA-made pant. I know I just said that if a pant is too comfortable it's probably too big, but I was mostly referring to if you're actually wearing the wrong size. These pants are cut to be roomy, and if they're too roomy for you, get 'em tailored. Don't be surprised if these become your favorite.

@ All Seasons Uniforms ($32)

2. Unis Gio

Eunice Lee makes great pants. Her Gio trouser is a favorite of mine and totally changed my concept of a chino. This pant will fit right in at the office and you'll want to wear it the rest of the time as well, and it'll hold up like a pair of jeans. Her garment-dyed colorways are always appealing, and the pant is cut in such a way that it's slim but accommodates a lot of different body types. You can take your normal size in these.

@ Unis ($148.50, on sale from $198)

3. Epaulet Rivet Chino

If you like Epaulet's pants, you may feel like you've hit the jackpot – their Rivet and Walt trousers come in a dizzying variety of colors and fabrics. They are extremely well made, with taped seams, cotton curtain at the waistband, and extra fabric at the center seam to make it easy to have them let out or taken in should you want to alter them.

@ Epaulet ($135, on sale from $195)

4. Bluer Denim Slim Straight

If chinos are hard to find, denim is even more nebulous. Because your jeans will be the pant you turn to hundreds of times every year, there's a lot of pressure to find the right pair. Bluer denim is made in the USA and designed in Portland, Oregon, and available in raw or washed 12 oz. denim. The great thing about Bluer is that they offer a home try-on with their denim, so you're not buying online without trying it on.

@ Bluer Denim ($98–$148)

5. Left Field NYC Greaser and Chelsea Jeans

If you're looking for some top-of-the-line denim, look no further than Left Field. Left Field flew under the radar for a while, but Christian McCann has been making tough-wearing clothes for years. The two cuts, the Greaser and Chelsea, come in a few different weights and are a straight fit and slim fit, respectively. I'd suggest sizing down in the Greaser and taking your normal size in the Chelsea, but what I'd really advise is that you consult the measurements on the website. The jeans can shrink up to 1.5'' upon first washing them, so take that into consideration as well.

@ Left Field NYC ($179–$210)