Shopbop 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.

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!

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 PA225229 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

5103018017_8a9fda7656_b 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.

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!)

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.

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?



ps.  Most of the leggings and tights pictured above came from the Topshop US site.  A few from Hue, Madewell, and Forever21.


  1. Ugh! Gorgeous! Everything. May I just inquire whether you already have or plan to purchase the Tabitha cowl neck sweater? I think I’m in love. . .

  2. Thanks, Lisa! Glad it helps!
    Mol – So funny, but I actually thought of you when I saw it…it’s all yours. I won’t be able to easily nurse in it. 🙂

  3. Shana, ok here’s a request. Or maybe you’ve covered it. Can you recommend brands of jeans that actually fit mom shapes? As in plenty of hips, thighs, and butt. I’m sitting here in my old too small Citizens because they’re all I have that quasi-fit. I so want to rock the skinny jeans but I absolutely hate the way most jeans fit me. They don’t fit well and I end up looking like a plumber. Budget-friendly is a plus because I’m still losing baby weight and don’t want to spend $150 on jeans I can’t wear in 6 months. Ideas? Something with medium rise and a little “give” in the hips/thighs is ideal. Thanks!

  4. Amber – Yeah, Yeah, LOL! I know. 🙂
    Lisa – You’re in luck! Well…if you don’t mind waiting a bit. We are currently working on an article on this very topic, and pulling ideas from some of the brilliant denim minds for help. So stay tuned. In the meantime, check out Levi’s curve id jeans. I’ve been too preggo to test them out myself, but have been hearing good things. You basically can choose your “curve ID” based on your body proportions, and the style of jean you’d like. Voila! A (theoretically) perfect fit. I’d love to know what you think of these, so please email or comment back!!

  5. @Lisa-I found some A.N.A. skinny denim leggings for less than $8 clearance at JC Penney that have some stretch on them and seem to have lots of room in the hips etc to me and could be a good option for a transition weight since they’re so cheap! You could even buy a couple pairs in different sizes to transition with you 🙂

  6. Wondering if you could help…I ordered the Frye Melissa satchel in Slate to wear with my black Frye boots but it arrived yesterday, dark brown. What shall I do? Free return shipping but it is gorgeous.

  7. Hello Shana.

    I like to think that when it comes to fashion there are no rules, but you can hold on to several key elements to create a perfect monochromatic outfit.

    I like wearing different shades of grey, and this always works as I get to create more depth in my look, and can highlight whatever I like. I don’t only chose for different shades but also different textures, allowing me to prevent a more boring look when I’m layering up.

  8. Can you do a new version of this post or something similar? I found it helpful but the pictures are now old and corrupted. Thanks for considering it!

Leave a Reply