Flat boots can be casual or dressy, they’re typically more wearable than heeled boots, and they look great with just about anything. That’s why they’ve become such a popular choice for fall and winter and have continued to maintain their “trending” status for several years running.

Women wearing flat boots

Even when they’re not topping the hotlists, I’m a huge fan of flat styles. However, it can be difficult to find boots that are completely heel-less. So, I usually like to expand my search to include boots that have heels of 1.5 inches or less. The extra inch or so doesn’t typically make much of a difference in how the boots feel, but it does give me access to a wider variety of styles. It also makes it easier to find boots that will work with dress clothes as well as with casual outfits.

Below are a few of my favorite flat and low-heeled boots for the 2020/2021 season.

Nine West ‘Partay’ – Classic and Affordable

When you’re looking for a pair of flat or low-heeled dress boots, you’re likely to run across a lot of riding boots. They’re great, but you don’t always want the buckles, the side tabs, or the western flavor that often comes with them.

Sometimes, you need a really simple boot that’s free of trendy or distinctive detailing. And, even though they can be a bit more difficult to find, the search is well worth it. Because if you do find such a pair of boots, you’ll have one of the most versatile items you can own. They’ll look good with jeans. Leggings and a long sweater. Dresses. Skirts. Really, just about anything. And, unlike higher heels, they don’t imply dressiness, and they’re far less likely to leave you in pain at the end of the day.

These boots from Nine West are just one example of such a style. They don’t have any trend details that are going to date them or limit what you can wear with them. And, even though they’re not completely flat, most flat-seeking women won’t mind their wide 1.5″ heels.

With pull-on styling, elasticized back panels, and suede or leather uppers, these boots come in brown or black, and they’d look great with just about any outfit you could put together. All those features, plus the reputable Nine West name, makes these boots a relative bargain at just under $170 per pair.

It’s difficult to find a pair of boots that are priced at nearly $600 and still have an average of 5 out of 5-star reviews from nearly 70 customers, but that’s exactly what these classic tall boots from Stuart Weitzman have going for them.

In addition to the fact that they just look fab, they also come in a dozen different colors and patterns. But, I think these boots are especially popular because they come in such a wide range of sizes (4 – 12) and widths (narrow, medium, and wide). And if that weren’t enough to satisfy the hard-to-fit, they also have elasticized back panels that give them that much-appreciated stretch.

With ultra-tall, 21″ shafts, and 1″ heels, these boots would look as good with leggings tucked into them as they would with flirty dresses floating above them.

Report ‘Baron’ – Lace-Up Grunge Boots

I am absolutely smitten with these casual, lace-up boots from Report. They’re grungy. They’re edgy. And, they’re a whole lot of fun.

Available in black and brown, these boots have distressed uppers and are priced at $140 per pair.

I also want to point out that just because a pair of boots is casual doesn’t mean they will only work with jeans. I think a lot of us are guilty of thinking in those terms. Casual = jeans. Dressy = dresses. Thankfully, the world is a lot less black and white than that, and there are thousands of gray shades in between those two extremes.

So, yeah, boots like these would look great with jeans. And with leggings. But, throw on a pair of tights, and they’d also be a super-cute match for skirts and dresses. You could even stack tights or wear socks over tights. Like I said, lots of grey areas. Endless options.

BC Footwear ‘It’s a Date’ – Cute Riding Boots

Riding boots are always a great choice when you’re looking for timeless, casual boots that will work with a variety of outfits. These particular boots are especially nice because they have full-side zippers, which makes them easy to put on and take off. Partial or full zippers are also nearly essential for women with high arches or insteps.

They’re also just a little bit different from most other riding styles. The rounded toes give them a bit of an engineer vibe, which definitely adds to the casual coolness of the overall package. I also really like the charcoal uppers. You don’t see a lot of riding styles in gray. They’re usually shades of brown, black, or the occasional dark red. This model does come in black too, so if you’re more of a traditionalist, you can give those a look.

While some riding boots work wonderfully with outfits that are on the dressier side, I’d reserve styles like this for more casual attire — jeans, leggings, or casual skirts and dresses. Mainly because of those round toes.

Priced at just under $150 per pair, these boots have shafts that are 17″ tall. This is a great height because it’s going to hit right around the knee on a lot of women.

DV by Dolce Vita ‘Charley’ – Easy to Wear Western

These casual ankle boots are kind of a cross between last year’s Chelsea boots trend and this year’s western boots trend. I like the combination. And, even though I don’t wear a lot of taller western boots, I do find myself drawn to western ankle boots, mules, and shoes. They look really good peeking out from under jeans — and they go great with cooler weather. Plus, they don’t require quite as much of a commitment as those all-out cowboy styles.

Whatever your personal preferences are, short boots like these have a lot going for them. You don’t have to worry about whether or not to tuck your jeans into them. Don’t.

Granted, flat ankle boots aren’t nearly as versatile as tall styles, but if you mostly wear jeans anyway, you may appreciate the fact that they’re also not nearly as cumbersome.

Available in black or brown, these suede boots ring up at just under $110 per pair.

Madden Girl ‘Cactuss’ – Cute, Casual, and Budget-Friendly

Here’s a western boot that’s a bit more traditional or, at least, taller than the boots above. Still, not a true cowboy boot, but more western. In terms of versatility, you’re going to be able to wear a western-inspired boot with a lot more outfits than you can a cowboy boot. Then again, maybe you don’t need a lot of versatility from your boots. Maybe you just want them to have the right attitude.

There are three big reasons these boots made this list. First, I like the height and style. They’re trendy but not over-the-top, and the stud-lined, red-taped back zippers are so eye-catching.

I also really like the colors. “Black Paris,” “Cognac Paris,” and “Brown Paris.” Which reads as black, cognac, and brown, with a bit of a weathered finish.

And finally, there’s the price. These boots are a bargain at just under $80 per pair. True, they’re made from synthetic leather, but that’s a big plus for a lot of people, and for those of us on a budget, it’s a win-win.

Leggings or skinny jeans would make the best playmates for these cute, casual boots.

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