No, it’s not rocket science, and yes, the key is to put the jeans on before your boots, but there’s still more than one way to wear boots with your jeans.
1. The Stack
Simple: do nothing. Put your boots on, pull your jeans over the shaft, let ’em stack up on top of the boots. Ideally, you don’t want wrinkles running all the way up your legs; instead, leave an extra couple of inches to your inseam and you’ll end up with nice honeycomb fades
Works best with: slim denim
2. The Micro-Cuff
Also simple – you know what, they’re all simple. In this case, you turn up the hem of your jeans – but not by much, just enough to leave a sliver of well-worn selvage denim showing. Vary this by accompanying it with a stack, or with a jean hemmed to a shorter length to show off the shaft of your boot.
Works best with: slim-straight jeans
3. The Regular Cuff
Cuff your jeans once. Done.
Works best with: slim, slim-straight jeans
4. The Double Cuff
For a thicker cuff, turn your hem over twice and your jeans should sit just at your ankle. This is an easy option that will look nice with most boots.
Works best with: slim-straight or straight jeans
5. The Triple Cuff
Not too hard – roll it up one more time. It’ll give you a thicker cuff, and although this looks good with heavy boots, I also like it with sleeker silhouette and taller shaft.
Works best with: a straighter-legged pair of denim so that the bigger cuff doesn’t overwhelm the leg of the jeans.
6. The Narrow Roll
Make like you’re rolling a single micro-cuff, and then keep going as high as you like. Wear the hem low to stack on top of your boots, or pull it high for a cool silhouette.
Works best with: straight or relaxed denim.
7. The Railroader
Only for the dedicated: instead of making small cuffs, turn your hem inside out and pull the cuff halfway up your shin. This has the potential to be massively rad or not rad at all – you need to back it up with an outfit that meshes well.
Works best with: stiff, straight-leg jeans and heavy boots (like engineer, combat, or service boots).