The Secret to Wearing Tall Boots with Jeans (For All Figures) by Kate Kashenbach

How NOT to wear your jeans and tall boots

I have had a few emails recently with women telling me it just doesn’t seem to look right when they wear their tall boots with jeans – and they’re not sure why. What are they doing wrong? Now, since I didn’t see the outfits in question (although, please feel free to send me any outfit pics with your questions!) — I’m going to guess what was happening. You’re thinking, “these are the most fitted pair of jeans I have — so those are the ones I tuck into my tall boots.” Or maybe, you have a pair of boot cut jeans (or wide leg, yikes!) that make you look like a rock star from behind, so you sort of peg them and tuck them into your socks — and stick the whole bulky mess into your tall boots. Sounds good, right?

Maybe they look something like above (or worse?)

Well, stop. Although, this might not look too horrible (especially on this model who has long legs), it definitely doesn’t look polished, is probably uncomfortable — and is most likely why you’re thinking something is off.

I’m going to now assume something else: you’re deathly afraid of skinny jeans. You are too old-tall-short-big-round-pear-apple-diamond-shaped to wear skinny jeans. Well, wrong again.

Honestly, the only trick to wearing tall boots with jeans: wear them with skinny jeans or jean leggings. That’s it. Trust me, you may not feel comfortable wearing skinny jeans with any other type of shoe, but wear them with your tall boots. All tall boots. And if you want to balance that out — wear a tunic or long sweater or cardigan. You will love it. I promise. Get the tightest fitting pair you feel comfortable wearing- – ideally it should be fitted from the knee to the ankle. No baggy knees above the boot please!

You may have heard me say denim is one thing I always buy designer — and I stick to that — however, if this is your first pair of skinny jeans and you aren’t ready to invest quite yet — I’m going to find some great skinny jeans and jean leggings that are REALLY priced well – they all range from $34- $99.

And — if it is your first pair — go for a dark denim, definitely the most flattering. Here are some outfit inspirations for you, and some skinny jeans for you to check out. Please send me your before and after photos!

The DDT: Skinny Jeans (All between $34-$99)

1. Gap $79.95

2. DKNY $49.95

3. Levi’s $34.97

4. Blank Denim $54.99

5. Treasure&Bond $58.90

6. Joe’s $99

~ Kate Kaschenbach, Fashion blogger of, personal shopper and stylist, Founder/CEO of KK Designs LLC accessories line.