Wellcultured - Well Cultured is a men’s online magazine with advice and reviews on fashion, dating, finances, health, music, movies and many other topics, as well as a robust message board and the Well Cultured Guide, a freely editable community wiki.

Are bootcut jeans OK? I have a lot of pairs of boots that just won’t fit into straight leg jeans.

Well, yes, generally. The generally accepted rule is that you try to wear jeans as slim as you can without looking ridiculous, but obviously, if you plan to wear boots, you’ll need jeans that work well.

To be more specific, you probably want to go for something along the lines of Levi’s 507 jeans — that is, slim boot cut jeans. The reason for the seemingly universal hate fashion websites have for boot cut jeans is that they are typically somewhat bulky and baggy, two things you never want in a good pair of jeans. Whatever brand/style you do go for, the best thing you can do is ensure that, independent of the bottom of the jeans, the jeans fit well overall.

Also, while I’m on this topic, let me be clear about the general policy on boots: cowboy boots always stay under jeans, military boots and other mid-thigh boots can be under the jeans or bloused depending on the style, and hiking boots generally stay underneath by virtue of being too short to really be blouse-able. In simpler terms, never ever “tuck in” your jeans on a pair of cowboy boots, no matter how skinny your jeans are — get a pair of bootcut jeans, or at least jeans that will accommodate the boot, or don’t wear them. You will look like a gay pornstar otherwise. That being said, military boots, or other types of boots with high uppers, can sometimes be bloused (meaning you tuck your pants into the boot), just be careful.

Either way, long story short, go for slim bootcut jeans for cowboy boots or certain types of boots, or otherwise go without or blouse your pants. Hope this helps!

If you live in the United States, chances are you have purchased or know someone who have purchased Levi’s jeans. As one of the staple jean brands in the US, Levi’s seems like a relatively boring choice to be pro-fashion — but on the contrary, they are some of the best purchases you can make. Though they may not be as expensively branded as other jean brands, Levi’s are an absolutely wonderful start to any wardrobe — they are cheap, are available in a wide variety of fits, and best of all, are available in virtually any city and all over the place online.

With that being said, here is a quick and dirty Levi’s sizing guide, so you know what to look for if you ever feel like purchasing a pair.

The Basic Sizing Guide

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Levi’s 501 (Original Jean)

Sometimes jokingly called the “Obama Jean” nowadays, 501s are the very classic Levi’s jean offering that has been around for virtually forever. 501s are as baggy as a fashionable person would ever want to go — they are relatively loose and relaxed and perfect for a look trying to exploit that, but really often too loose for most guys otherwise. Unless you have huge legs or are trying to pull off something retro (or just have no other choice), 501s are probably not an ideal choice.

Levi’s 514 (Slim Straight Jean)

These are pretty much the perfect balance between straight and skinny — 514s are neither skinny nor baggy straight, making them a “slim straight” that works fairly well for most people, particularly those with bigger thighs (i.e. weightlifters). 514s don’t work very well for those with super thin legs (they just manage to look baggy), but for those with muscle tone, 514s are a godsend.

Levi’s 511 (Skinny Jean)

The canonical “skinny jean”, though admittedly they are really only skinny in name. 511s differ from 514s in that they have a more drastic taper and try to achieve a more skin-tight look without trying to be too skin tight, making them a good choice for most guys with relatively thin legs. You can find a ton of variations on 511s, from ones with wild colors (like hot purple) to material additions (like spandex to make the jean material less constricting). These allegedly have a wider seat than the 514s (which is really not something I’ve personally seen), so be wary.

Levi’s 510 (Super Skinny Jean)

510s are the honest-to-god Levi’s skinny jean. These can look amazing on guys with very thin legs, or very horrible on guys with anything but slim legs — if you don’t know if you could wear these, chances are you shouldn’t wear them. 510s are skinny to the point where they look ridiculous unless you are skinny all throughout to the point of looking emaciated, so be careful — these are wonderful jeans only in the right hands.

Some General Tips

• If you live in the United States, Levi’s can be purchased at a huge number of department stores. However, I personally feel one of the best options is the Amazon.com Levi store, which sells virtually all types of Levi’s for around $30/pair, which is an incredible steal.
• Consequently, if you live in Europe or outside of the US, Levi’s will be much, much more expensive, and you may find a better brand. Be wary — this guide is really meant for American users, as Levi’s business model intentionally cuts the price of the jeans stateside.
• As with virtually every other jean brand, waist size is directly correlated with the bagginess (or slimness) in the legs. Thus, focus on determining your waist size, and then experiment with the different styles listed above. You can have drastically different leg sizes and fits with a size 32 waist — some people can wear 510s with a size 32 waist, others have to go up to 514s, and so on.
• In the slimmer cuts (particularly 510s and 511s), the waist can and likely will stretch ever so slightly, as will other parts of the jean if they are really tight. This is not to imply you want to buy jeans you have to use a shoehorn to get into, but in some cases small amounts of tightness in the waist fix themselves after a little bit of wear. The same rule applies to the thighs.
• Darker wash Levi’s — particularly the raws (obviously) and the “rigid” brands — do develop fairly nice stacks, whiskering, and general signs of individual wear. Obviously, the “rigid” Levi’s are not going to develop effects as nice as raws, but it’s a great alternative.
• No matter what people on other fashion websites/forums may say, there is no inherent status involved with waist size or the style of jeans you wear, pending they fit well. You don’t get fashion benefits for wearing 510s or anything like that.