Since posting Part 3 of our Style Rules for Moms, where we discussed the importance of tall boots, we’ve been fielding both emails and comments from readers wondering which color of leggings/tights/etc to pair with the new pair of <InsertAnyBootColorHere> tall boots they just bought.
It’s a good question.
Part of the answer, however, lies in the fact that our very last style rule was this: mix it up. Clear your head of the notion that shoes, bag and belt must always match. Think of black and brown as being new BFFs. And those harder-to-describe shades? Tan-ish, caramel-y, taupe? Even gray? Your new go-with everything neutrals.
Take a look at the picture above, from Shopbop’s fabulous Shoptalk blog. This is one of my favorite inspirational outfits for Fall. Notice that she’s wearing black tights, taupe-y shoes, army green shorts, a gray sweater, and a cognac bag. Yet it all works. Why? Because, in this pic, she’s really just wearing a bunch of neutral colored clothing. Consider black, taupe, tan, gray, army green, and shades of cream to all be neutrals. Mix with wild abandon.
So how to translate this answer into your everyday boot outfit?
1. Denim Goes With Everything
I don’t care if it’s dark-wash denim, medium wash, or light-wash denim, but denim looks good with virtually all tall boot colors.
TallBootsWithDenim by aintnomomjeans featuring round toe boots
2. Black Goes With Everything
When used as a base (tights, leggings), black is fool-proof. It slims legs, and just fades into the background – no matter what else you are wearing!
BlackLeggingsandBoots by aintnomomjeans featuring flat heel boots
3. When The Black Boots Don’t Match the Black Leggings
What happens, one reader asked, if your blacks don’t match? Faded black boots, when paired with black 
leggings or tights, often come off looking…well, a little faded. While it’s true that keeping the color monochromatic will make for a longer leg line, personally, I think it’s fine for blacks to be off a bit. But I realize that I have a tendency to love the mis-match (navy and black, brown and black, etc).
If you hate the way your faded black boots look with true-black leggings, either try to offset the gray-ish look of the boot with some gray on top (like I inadvertently did at right), or try some charcoal colored leggings instead of black. A good charcoal (as opposed to a lighter silver gray) is just as slimming on your legs as black, and has flecks of both gray and black.
4. If Your Outfit is Monochromatic, You Can Be Crazier With Leg Color
I love this look from fashion blogger Karen, of Where Did You Get That? It’s totally irreverent, easy, and crazy-stylish.
Black is the easiest outfit color to pull off this styling trick. If you are wearing a black sweater, black jacket and black boots, look for leggings in a fun print to break it up, or try for a pop of color. Nervous? Try a soft burgundy.
4. Need More Ideas?
Here are a few unexpected pairings that work in addition to denim and black. This is not a complete list, just some of my favorites. If you see gray tights, with, say…chocolate boots, please don’t think “Shoot! I was hoping to wear my gray leggings with my tan boots!” If you love it together, it probably looks good! My list below is merely to offer up some ideas to help you visualize what you like.
Cognac & Brown Boot Pairings
In the grouping below, I love the deeper marine blues with cognac boots. I also love a true chocolate brown paired with a charcoal gray. But to my point above…I often wear charcoal gray with my cognac boots. Why? Because I don’t have brown boots. I have cognac. We’re not striving for perfection here, Mamas. Don’t over-think it.
Tan&BrownBoots by aintnomomjeans featuring flat boots
Olive & Gray Boots
This next set shows some really fun pairings…and with the exception of emerald green, the tights and legging colors pictured below actually work with either pair of boots. (And am loving the fake-leather, shiny-black leggings with suede boots – so much fun texture!)
Olive&GrayBoots by aintnomomjeans featuring nine west boots
Black Boots
There many different shades of black. I tried to show both a shiny black boot and a faded black boot…but ultimately, it doesn’t matter: all legging/tight choices below work for either pair.
BlackBoots by aintnomomjeans featuring steve madden shoes
So let me reiterate: mix neutrals (gray, taupe, tan, caramel, cognac, black, army green, etc.) with wild abandon. Throw in pops of color for fun. Try not to over-think. Bottom line: If you love it…success!
Readers, did I miss a go-to boot/legging color pairing that you love?
xo,
S
ps. Most of the leggings and tights pictured above came from the Topshop US site. A few from Hue, Madewell, and Forever21.
