How To Wear Ankle Boots With Jeans
Wear ankle boots with jeans however you want. Nothing about men's fashion or whatever is scientific or maintained as a standard by the Department of Weights And Measures.
But...if you wanted to really do it right...there are definitely a few finer points that can help you look your best.
You buy a pair of heritage boots because they feel and look great. If you're going to get a pair of boots because they look good, having the rest look great too is a good idea.
Pair Quality Ankle Boots With Quality Jeans
First, get some decent jeans to wear with your boots. It should go without saying, but quality jeans can last a very long time if properly cared for.
Just like a great pair of leather boots or a leather jacket, they develop a patina with time that will just look better and better.
Levi's are a good starting point, but there are some better options out there. If you're getting boots because they make a great appearance as well as being made as well as they can be, you should have jeans that are too.
Hemmed Or Rolled Cuffs
Classically, you'd make sure your pants had the correct hem length. Today, it's become fashionable to roll up the cuffs to just above the ankle.
You pick whichever you want.
A rolled cuff will work better with slim-fit jeans, but will appear baggy with a relaxed or regular fit. What you're looking for is a tight, precise roll of the cuff, so it looks uniform.
If you don't want to roll up the cuffs, it's important to make sure your pants are the correct hem length. If your jeans drag on the ground, they'll start to get scuffed until they eventually start to tear, usually being the heel.
Buying bootcut jeans can help a little, but the hem is the right length or it isn't.
What you're looking for is a good half-inch or more of clearance between the ground and the cuff at the heel. Any less and you're likely to drag. Closer to an inch of clearance is better.
While pants are normally made to standard inseam lengths (30, 32, 34 inches) the fact is not everyone actually has that exact inseam. It used to be a lot more common for men to have their pants tailored for this reason.
Hemming is usually cheap, so don't be too averse to having it done. If you're handy with a needle and thread, you can try doing it yourself. It isn't terribly hard, but does take some precision.
Contrasting Colors: Matching Ankle Boots With Denim
Jeans aren't formal wear, so you don't really need to follow conventions like black going with everything and wearing brown with certain colors only. A bit of contrast is actually a good thing; that will make your ankle boots pop.
Dark leather goes well with lighter shades of denim, so a classic stonewash will go really well with a dark brown or black. Likewise, a lighter or even orange-tinged shade of brown will contrast well with dark blue or black jeans.
The contrast will highlight the boots you're wearing, and show off the leather. If you're investing in some boots with the highest-quality leather, show them off and feel good about it.
Just Don't Forget To Buff And/Or Polish
Whether you want to polish your boots or not is up to you. Some people like to put a high mirror shine on their boots. Other people don't want to spend hours buffing their shoes!
Pull-up leather can get a dull shine quickly with oiling and a quick buffing. Polished leather takes time to get perfect and regular maintenance to keep it that way.
The dull shine of oiled, buffed leather or the high mirror gloss of perfectly polished boots will also make your ankle boots stand out with a great pair of jeans, so take some time to keep yours in good condition.
It's better for their appearance AND, if you're using high-quality polish or other boot care products, really good for the leather too.