Boots 101

With winter upon us and the end of the 40-Day No-Buy* just days away, it’s a good time to talk about my favorite subject, boots.

Boot are a fantastic foot casing for a number of reasons. Practical, warm, hardworking, durable, fashionable, they’re a statement piece, with a statement worth making.

So I’ve put together a boot primer, what to wear different boots with, a few caveats and rated each type of boot on a “difficulty to style” scale of 1 to 5 If you have specific questions or ideas about how to wear boots, please leave your thoughts in the comments below. If you have any curiosity about boots and socks, please check out this article Sock Love.

Here are the boots –

Ankle Boots

Simple, warm and understated, ankle boots are an easy first step for most people into the glorious world of boots.

A simple Chelsea boot would be a great place to start.

Wear with: Cuffed jeans, ankle pants, casual trousers. If you are feeling adventurous, try them with tights and skirts

Teva boots are durable and easy to wear.

Be aware of: Channeling an elf. Skinny jeans and pointy toe ankle boots can bring you dangerously close to looking like you popped out of a Christmas special, particularly if you are given to striped shirts. Save pointy-toe versions to wear with more fluid pants.

Difficulty to style: 1

 

Lace-up Ankle Boots

These have a decidedly casual feel. They look great with a flannel or cozy sweater and jeans. They are a good choice for a weekend spent outdoors, spectating at a sporting event, or a casual event with friends.

Wear with: Jeans and casual pants are the easiest, but they also look good with a shorter fitted skirt, a knit dress, or cords. You can even try them with a flowing skirt for a 1980s look.

Be aware of: a military and/or Laura Ingalls Wilder vibe. These do well with fitted pants tucked in to them and a fuzzy sock peeking out the top, but a looser pair of pants tucked in to lace up boots will recall images of combat that you probably aren’t going for. And unless you long for a homesteader look, when you wear them with a dress or skirt, skip the calico.

Difficulty to style: 3

My favorite Timberland boots.

 

Mid-calf Boots

A mid-calf boot is more casual than a tall boot, and a little more edgy. Moto boots and harness boots fall into this category. A well-worn pair of favorites is absolutely effortless-cool.

Wear with: Dresses, skinny jeans and pants tucked in, chunky socks

Be aware of: The fact that you won’t ever want to take them off.

Difficulty to style: 2

 

Tall Boots

A great way to stay warm on a dress-up occasion, boots hitting just below the knee in suede, soft leather or some other buttery material are a great addition to your wardrobe.

This looks fun.

Wear them with: an above-the-knee knit dress or skirt, dark skinny jeans, leggings, or with a longer a-line skirt. When in doubt, feel go with tall black boots and black pants.

Be aware of: The hem of your skirt competing with the tops of your boots. Give yourself at least 5 inches on either side of your hem with tall boots. Knee-high boots with a knee-length skirt is just too much action around the middle of your legs.

Difficulty to style: 2

 

Riding Boots

Riding boots are so elegant… which is probably why I don’t wear them very often. Whenever I see a woman in tall, simple riding boots I always admire the look, but I’m just not in an elegant stage right now. If you are, invest in a great pair and enjoy endless classic looks with them.

Wear with: Long skirts or dresses, a sleek pair of jeans or pants, or substantial leggings and a sharp blazer. Keep the whole look long and lean with a streamline jacket or tunic.

Be aware of: Tight calves. Make sure your boots have some room in the calves so you can move, and even layer them with socks if you want to. Bjorn and other companies make wide calf widths for those of us with leg muscles.

Difficulty to style: 4

 

Mud Boots

It is hard for me to express how much I love mud boots. Warm, dry feet encased in a comfortable shoe are a beautiful thing.

My faithful mud boots.

Wear with: whatever you wear when walking through the mud

Every pair of Bogs is tempting

Be aware of: trying to make them into something they are not. Mud boots are pretty trendy right now, with Sperry and AE marketing their take on the duck boot, and everyone running around in her Hunter boots no matter what the weather. So long as there is mud on the ground, and you are going to be outside at some point, these are totally appropriate. If it’s 70 degrees and you are driving to the mall, I would skip the mud boots.

Difficulty to style: 0

LL Bean with the classic

Snow Boots

As with mud boots, when the weather calls for snow boots there is nothing more wonderful. Mine feel like I am wearing two fuzzy hugs on my feet.

Wear with: fun patterned leggings, regular leggings, jeans, knit skirts or dresses with cozy tights.

Be aware of: your intentions. Snow boots will keep you warm and look fantastically stylish. But like mud boots, if they are not worn for practical purposes they wind up looking a little off. It also goes without saying that you should never wear snow boots with bare legs, because that’s just silly.

Difficulty to style: 2

 

And finally, here are a few types of boots I don’t wear but you might want to

Over-the-knee Boots

For a night out, a pair of elegant, simple suede knee boots could be really fun.

This will never be my go-to on a Friday night, but they might be yours.

Wear with: something simple like a solid-color fitted dress, leggings and elegant top, or a short swing dress.

Be aware of: any busy detail. Over the knee boots are statement enough in themselves. Any flashy embellishments will look like you are trying too hard.

Difficulty to style: 5

 

High-heeled Booties

There are all sorts of heeled booties on the market right now, ranging from chic to sexy. They are a nice alternative to classic pumps.

Maybe for work?
Probably not for work.

Wear with: Slacks or an elegant skirt or dress for work, a party dress or trendy jeans for going out.

Be aware of: I hate to sound like a grandma here, but these can look a little cheap. Make sure yours are high quality, and remember the more the shoe has going on, the less your outfit should.

Difficulty to style: 4

 

Cowboy Boots

I love the look of a confident woman in a well-worn pair of cowboy boots. To pull them off, the boots need to be authentically you. I’ve always thought that when I turn 50, I’ll but myself a really great pair and wear them everywhere for the rest of my life.

Someday.

Wear with: Anything casual, jeans, pants, flowing dresses. Personally I think they would be tough to wear with a suit, but that didn’t stop George W Bush.

Be aware of: Inauthenticity. Cowboy boots can smell your fear and they just won’t work for you unless you are all in.

Difficulty to style: this all depends on you

 

Do you have a favorite pair of boots or way to wear them? Leave you ideas in the comments below.

* If you are new to Mud and Grace and don’t know about the 40-Day No-Buy, check it out – Prepare for the No-Buy Style Challenge