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The New Rules For Wearing Tall Boots Over Skinny Jeans

October 14, 2019

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Are tall boots over skinny jeans back?? This is such a polarizing topic. As evidenced by the responses to our IG story last week (asking this very question), 60% said yes, 40% said no, and our inbox was promptly flooded with DMs from readers saying either a) tall boots over skinnies never left, or b) tall boots and skinnies are dead, gone and buried.

I get it — I’ve been all ankle boots and over-the-knee for a really, really long time.

So when did tall boots over skinny jeans actually die? We’re not exactly sure…but it looks like somewhere around 2013? 2014? Tall boots started creeping back into favor recently, however, as midi dresses (and skirts) gained in popularity. Know what goes amazingly well with a midi? TALL BOOTS.

The New Rules For Wearing Tall Boots Over Skinny Jeans

But I want to talk about tall boots over jeans. The way we wore this look the first time around (pre-2014) still feels…dated. Remember the look? Tall, flat riding boots — usually in a solid brown or black, rounded toe — with skinny jeans and some sort of long sweater, that was the uniform Truthfully, many of us are not ready to go there again. And yet…there have been a few (recent!!) instances where tall boots over skinny jeans made me swoon.

What makes the difference?

Well…we’ve been debating this, over here at The Mom Edit office. And after much discussion, we came up with a few guidelines (for lack of a better word) to rock tall boots with skinnies…as well as some advice on picking a tall boot that will feel fresh.

1. Tall Statement Boots Are A Sure Bet (Especially Snakeskin)

sweater (sustainable!) (xs) | jeans are sold out – here are the same jeans, different wash (25) – plus size option here (sustainable!) | boots (old, few sizes left) – or try the same pair in this season’s colors | bag (sold out – try this one)

I picked up a pair of these brightly colored, tall snakeskin boots during the holidays last year. I initially wore them with skirts (think: a dramatic ball gown skirt – see the outfit here)…but I found, in the freezing winter temps — that these boots were such a statement that they even felt fresh over skinny jeans!

My snakeskin boots are from last season, but they’ve been released again, with new colors. You can find my current favorites in last week’s article: Sweaters, Jeans & Tall Statement Boots: My New Go-To Party Uniform.

But I’m not the only one loving tall snakeskin boots with jeans. Reformation (whose styling I adore) recently showcased their recycled cashmere sweater by styling it with skinny jeans and tall snakeskin boots, too.

2. Try The New Neutral: Taupe

Instead of those old brown riding boots…try lightening up. Taupe (or beige or even white) definitely looks fresher. It’s part of the giant white sneaker phenomenon, but much easier to wear.

tee (xs) – plus size option here | jeans (25) – plus size option here (sustainable!) | boots | bag (sold out – try this one)

3. Choose A Tall Boot With a Heel…And a Pointy Toe

I keep trying to find a tall, flat boot that I’d be willing to wear over jeans. Aaaaaand…I’m still lookin’. But sexy tall boots — the ones with a bit of a heel, a pointed toe — these boots I love over skinnies.

jeans (25) – plus size option here (sustainable!) | boots | bag (sold out – try this one)

4. Look For a Lower-Shaft Boot…With Some Slouch

The neutral boots I’m wearing above are a few inches lower than traditional knee-high boots, which is yet another reason that they look fresh. Take this up a notch by finding a tall-ish or mid-calf boot with some slouch. Both Free People and Shopbop have a perfect examples of this:

black boots (Free People) | tan boots (Shopbop)

5. Stick With High-Rise Jeans (And Tuck In That Top!)

I suspect there’s a long, slouchy sweater somewhere that I *could* wear with my updated tall boots and skinny jeans…but it would require a half-tuck (to show off that waist) in order to keep the look current. A much safer bet, for sure, is go all in on the high-rise. High-rise skinnies and a tucked-in top is the easiest way to make your tall boots feel modern and fresh.