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Before you decide your boots are outdated or that you need a new pair, try them with a different style of pants. Sometimes your closet isn’t the problem—it’s simply how you’re putting the pieces together. It’s not just what you wear, it’s how you wear them!
A few guidelines to keep in mind - Hem meets boot, long & lean goes with long & lean, and bulky goes with bulky Hem meets boot - mind the gap! with CROPPED JEANS Best boot: A taller-shaft ankle boot The hem of your pants should meet the top of your boot—or overlap it. You don’t want an awkward strip of skin showing between the bottom of your pants and the top of your boots. That gap breaks up the leg line and can make you look shorter. The biggest issue here is often the gap between the hem and the boot. Choose a boot with enough shaft height to meet the hem of the jean to avoid the shortening affect and also camouflages a fuller calve. Sometimes it isn’t the boot that looks wrong—it’s the amount of space between your boot and your jeans. Long & lean goes with long & lean with WIDE-LEG JEANS OR PANTS Best boot: A boot with some height and an angular toe - we want to avoid the clown shoe look. With all that volume in the pant, you don’t want your foot to disappear.A pointed, almond, or slightly elongated toe helps extend the leg line. A heel can also givethe illusion of a longer looking leg. Your classic Win-Win scenario! Watch the hem length. Ideally, the pant should hit just above the floor rather than puddling around the boot. Bulky Goes with Bulky for BARREL OR CUFFED JEANS Best boot: A boot with some visual weight Barrel jeans already have volume and personality. A tiny, delicate boot can appear unbalanced. Try lug-sole boots, or chunkier ankle boots. The more visual weight you have in the pant, the more visual weight your shoe or boot can handle. Match the opening to the opening with STRAIGHT-LEG JEANS Best boot: A slim, close-fitting ankle boot If the pant is going OVER the boot, make sure the pant opening comfortably clears the boot shaft. If the pant ends ABOVE the boot, pay attention to the amount of ankle showing between the two. If the pant goes INSIDE the boot, keep the pant slim enough that it doesn’t bunch. The jean should fall cleanly over the boot shaft instead of bunching or getting caught on top of it. SKINNY JEANS & LEGGINGS Best boot: Knee-high or tall boots Skinny jeans work beautifully as the supporting piece underneath a tall boot. The tall boot also adds visual weight to balance any hip curve. Adding a longer jacket, sweater, or other third layer piece completes the look. You don’t necessarily need to get rid of your skinny jeans. Think about wearing them differently. (For more ideas on how to make skinny jeans current, see my post here.) THE BIG TAKEAWAY Hem meets boot, long & lean (pants) go with long & lean (boots), bulky (pants) go with bulky (boots) Sometimes your closet isn’t the problem—it’s simply how you’re putting the pieces together. It’s not just what you wear, it’s how you wear them!
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Dani SlaughImage consultant and personal stylist since 2011. Dani is happily married, the mother of 3 charming children, and an Aussie named Josey Wales. Archives
June 2026
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