Red Wing shoes can be worn with jeans, in fact it is actively encouraged! Boot-cut style jeans look the best as their slightly flared bottoms give plenty of space to comfortably fit over the shoes and allow them to naturally show off their shape and form.
Generally speaking, you should avoid skinny-fit and slim-cut style jeans when you wear Red Wing shoes. Skinny jeans are designed to fit straight to your skin, giving no room for your boots or to move around in. One exception to this rule, is if you're going for an alpine-punk look, in which case distressed skinnies would look great with your Red Wing shoes. If you have a pear shape body, or if your legs are a little chubby, you can wear slouchy or baggy jeans. Pear shaped and larger people should generally try to avoid skinny and tight jeans as they fit to your legs very tightly and so it's a very unflattering look for them. If you're in doubt, leave them out!
As mentioned at the beginning of this article, the best look comes from boot cut jeans as they have a slight flare at the bottom which allows even the largest models of Red Wing boots to fit snugly underneath. However, if you do not like boot cuts or feel that the weather is too hot or otherwise unsuitable for them, there are a couple of other options. Firstly, you can wear cropped jeans or pants - these are jeans that are designed so that they stop above your feet, often just three quarters of the way down your leg. When paired with Red Wing shoes, these will appear to stop just above where your shoe begins, giving a very natural looking transition from pants to shoes.
The second way of getting around the boot-cut jeans problem is to roll the bottoms up. This can be done on any style except for the tightest styles of jeans and pants, but is especially good on straight-cut jeans as they give an even roll-up. If your jeans are a raw denim style, dark color or feature a very distinctive or dominant selvage, it is already very on-trend and fashionable to wear your jeans with roll-ups. The best roll-ups are those about 3-4 inches in height, and sit just on the peak or slightly below the top of the shoe. If you are wearing Red Wing boots rather than shoes, take take to overlap a few inches of the boots as otherwise you will look unbalanced and disproportionate. If you're wearing Red Wing shoes, feel free to wear the jeans rolled up so that they are sitting just above the top of the shoe.
If you're wearing your Red Wing shoes in a casual way, be sure to accessorize correctly. Try to wear a belt that matches the shade of your boots or shoes. They need not be an exact match, but avoid mistakes like wearing a green belt with a mahogany colored shoe. If the weather demands it, do not forget to match up your outfit with a hat and scarf. If you are not sure what color your hat and scarves should be, try this to begin with. Match your scarf with your belt - the more exact the match the better. For the hat, you'll need a similar (but not identical) color and a similar 'spirit'. Extravagant scarves require extravagant hats. Do not match a 3-tone, goose feather, body-curler scarf with a blue and red baseball cap. Keep things simple to start with too. Once we you gain a little confidence you can start experimenting with different colors and styles. If you insist on wearing gloves, try to get those that match with the belt and scarf.
When shopping for Red Wing shoes, it is vital that you get the right size. They must not be too tight around your feet and legs as that would detract from the flexibility it would offer. On the other hand, they must not be too loose so that they slop behind you as you walk. This would lead to blisters, uncomfortable feet and potentially risking falling over and injuring yourself.
