10 Fall Boots Every Woman Should Know and What to Wear with Them

I love fall for a lot of reasons, but the boots are definitely high on my list.

The minute the weather cools down, I start thinking about ankle boots, tall boots, suede boots, riding boots and all the outfits I can finally pull back out of the closet.

But I also know how easy it is to see a beautiful pair of boots, fall in love with them, bring them home and then realize I have absolutely no idea what I’m supposed to wear with them.

I’ve done that.

More than once.

So this isn’t going to be one of those guides that tell us we need twelve new pairs of boots before October.

I wanted to put together the kind of fall boot guide I would actually use.

What are the different styles?

What would I wear with them?

What should I think about before buying them?

And most importantly, how much can I actually wear them?

Because if I’m spending money on a pair of boots, I want those boots working.

1. Ankle Boots

Ankle boots are probably one of the easiest places to start because they can work with so many things.

I’d wear a sleek ankle boot with straight leg jeans, cropped jeans, trousers, a midi dress or a skirt with tights.

If the boot has a slimmer shape, I also like it under wider pants because it doesn’t fight with the bottom of the pant leg.

And despite what social media tells us every few years, ankle boots are still around.

 What changes is how we wear them.

I’m seeing them with straight jeans, wide leg jeans, flares and more relaxed pants instead of only that old skinny jeans and bootie combination.

If I were buying one everyday pair, I’d probably choose black, dark brown or cognac with a comfortable heel.

Because a gorgeous boot I can only survive in from the car to the restaurant is not my most useful purchase.

2. Chelsea Boots

Chelsea boots are the ankle boots with the stretchy panels on the sides.

They’re easy to pull on, usually comfortable and can look polished without feeling too dressy.

I’d wear them with straight leg jeans, leggings and a longer sweater, casual trousers or a sweater dress.

A chunkier Chelsea boot can make a softer outfit feel a little less sweet.

A slimmer Chelsea boot works when I want something a little more polished.

The thing I watch is how wide the top of the boot is.

If the opening is really bulky, certain jeans can catch on it instead of falling cleanly over the boot.

That tiny detail can turn a cute Pinterest outfit into me standing in front of the mirror pulling my pant leg down every thirty seconds.

3. Knee High Boots

Knee high boots are having a strong moment again, and honestly, I’m happy about it.

They work with sweater dresses, midi skirts, shorter skirts with tights and skinny jeans tucked inside.

Yes, skinny jeans.

They have apparently survived yet another internet funeral.

If I’m shopping for knee high boots, though, I’m checking more than the shoe size.

I want to know the calf measurement.

I want to know how tall the boot is.

A boot can technically be my size and still refuse to zip over my calf like we’re having a personal disagreement.

And where the boot hits on my leg matters too.

A knee high boot on a woman who is 5'2" can sit very differently than it does on someone who is 5'9".

This is why I like trying tall boots on whenever I can instead of assuming my normal shoe size tells me everything I need to know.

4. Riding Boots

Riding boots are usually flatter, cleaner looking and more structured than some other knee high boots.

I’d wear them with skinny jeans and a sweater, leggings and a long cardigan, a casual dress or a skirt with a fitted knit top.

They’re especially good if I want a tall boot without a high heel.

Riding inspired boots are getting a lot of attention again this fall, but I wouldn’t buy them only because they’re having a moment.

I’d buy them because they’re the kind of boot I can see myself pulling out year after year.

That’s the difference between a trend I like and a trend that actually deserves my money.

5. Suede Boots

I love suede in the fall.

There is something about brown suede with denim, cream, camel, olive, burgundy or black that just looks like fall without trying too hard.

Brown suede boots are especially noticeable this season.

I’d wear suede ankle boots with flare or straight leg jeans.

I’d wear suede knee high boots with a sweater dress or midi skirt.

Western suede boots can look really good with a flowing dress.

The catch is care.

If I live somewhere that gets a lot of rain, slush or snow, suede may need more attention than smooth leather or another weather friendly material.

Cute matters.

So does whether I’m afraid to step in a puddle.

6. Western Boots

Western boots have been hanging around for a while, and they’re still very much part of fall fashion.

I think the easiest way to wear them is not to make the whole outfit Western.

I’d pair them with a simple midi dress, straight jeans and a sweater, a denim skirt or even a softer long skirt.

If my boots already have stitching, a pointed shape and a strong Western look, I personally don’t need a fringe jacket, giant belt buckle and hat joining the meeting.

The boots can speak for themselves.

That’s what I like about them.

One pair can give a basic outfit some personality without me having to add much else.

7. Slouchy Boots

Slouchy boots are softer around the leg instead of standing completely straight and stiff.

They’re back in a noticeable way this fall.

I’d wear them with a simple knit dress, a knee length skirt and sweater or underneath a longer skirt.

Because the boot already has some volume, I’d keep the rest of the outfit fairly clean.

This is also one of those boots I’d really want to try on first.

There is a fine line between relaxed slouch and “why do my boots look like they’re falling down?”

8. Combat and Lug Sole Boots

Combat boots and lug sole boots are the practical girls of the boot family.

They can handle colder weather, the thicker soles can give us more grip and they can make dresses and skirts feel less dressy.

I’d wear them with straight jeans, leggings, a casual sweater dress, a floral midi dress or a skirt with tights.

One thing I pay attention to with chunkier boots is weight.

Some boots look fantastic sitting on the shelf and feel like I strapped two bricks to my feet after an hour.

I want sturdy.

I don’t need a lower body workout every time I go grocery shopping.

9. Heeled Boots

I love the way a heeled boot can change an outfit.

A simple pair of jeans, a fitted top and a blazer suddenly feels like I made plans.

I’d wear heeled ankle boots with trousers, straight jeans or a midi skirt.

A heeled knee high boot works beautifully with dresses and skirts.

But this is where I have to be honest with myself.

How much walking am I actually doing?

Where am I wearing them?

Can I stand in them for more than twenty minutes?

A lower block heel usually makes more sense for my everyday life than something extremely high.

I’m not buying shoes for the imaginary version of my life where someone drives me directly to a velvet chair and I never have to cross a parking lot.

10. Square Toe and Pointed Toe Boots

Toe shape sounds like a tiny detail until my toes disagree.

Pointed boots can look sleek and dressy, but they may feel tighter if I need more room across the front of my foot.

Square toe boots can give the front of the shoe a roomier shape, although the actual fit still depends on the boot.

I’d use the toe shape to change the feel of the outfit.

A pointed toe feels sharper and dressier.

A square toe can feel a little more modern and relaxed.

But comfort wins.

Every time.

What I’d Buy If I Were Starting My Fall Boot Closet Over

If I were starting over, I wouldn’t buy every boot on this list.

I’d start with an everyday ankle or Chelsea boot that works with several pairs of jeans and pants.

Then I’d add a knee high or riding boot that works with dresses, skirts, leggings and skinny jeans.

After that, I’d let myself have one pair with some personality.

Maybe Western.

Maybe suede.

Maybe slouchy.

Maybe a color that makes an otherwise basic outfit more interesting.

That alone gives me a lot of outfits without filling the bottom of my closet with boots I barely touch.

And before I bought any pair, I’d ask myself one question:

How many things I already own can I wear with these?

That question has become much more useful to me than asking whether something is trending.

I love fashion.

I love seeing what’s new.

And I completely understand the thrill of finding a pair of boots that makes me want to build an entire outfit around them.

But I also want my closet to make getting dressed easier.

The best boots aren’t necessarily the pair everybody is posting this month.

They’re the ones I keep reaching for because they fit, they feel good and they work with the clothes I actually wear.

And if they make me feel a little better when I walk out the door?

Even better.

#EvolvingWomanhood

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