January 13, 2017
Jessica Tegerstrand
Emily Applekamp

Women’s Casual Ankle Boots Buyer’s Guide

Active Junky selected 10 pairs of women’s boots from the best footwear companies and hit the pavement and the trail to help guide you to the best ankle boots to get you through the cold and wet months.

Editor's Pick The North Face Bridgeton Lace Leather

The North Face Bridgeton Lace Leather

Best for – Throwing on when braving snow drifts or slushy streets. Our top pick for navigating the winter months with style.
$96.22 + 9% Cash Back
Buy Now
Also Great Merrell Sugarbush

Merrell Sugarbush

Best for – Bringing a little trail style to the street. Our top choice for casually hitting your favorite trail.
$179.99 + 10% Cash Back
Buy Now
Also Great Ahnu Chenery

Ahnu Chenery

Best for – Being on your feet all day, from fall evenings out bar-hopping to hosting a local event and on to the after-party.
$179.95 + 10% Cash Back
Buy Now
Columbia Women’s Cityside Fold Waterproof Boot

Columbia Women’s Cityside Fold Waterproof Boot

Best for – Navigating city sidewalks during moody shoulder seasons.
$94.90 + 8% Cash Back
Buy Now
Helly Hansen W A.S.T 2

Helly Hansen W A.S.T 2

Best for – A long day on your feet on serendipitous evening racing between adventures despite the weather.
$150.00 + 0% Cash Back
Buy Now
Keen Reisen Zip Full-Grain Waterproof

Keen Reisen Zip Full-Grain Waterproof

Best for – Rainy day errands; frolicking around slippery waterfalls and jumping puddles.
$159.95 + 12% Cash Back
Buy Now
OluKai Nani Kamea

OluKai Nani Kamea

Best for – Adding classic elegance to any outfit. Our pick for cocktails on the patio with the girlfriends.
$259.95 + 10% Cash Back
Buy Now
Salomon Hime Mid LTR CSWP

Salomon Hime Mid LTR CSWP

Best for – Warming your feet up after hitting the slopes. Our pick for an après ski casual dinner.
$102.00 + 6% Cash Back
Buy Now
Teva De La Vina Low

Teva De La Vina Low

Best for – Turning up your tough factor; kicking up a little dust and getting into a little trouble.
$139.95 + 12% Cash Back
Buy Now
UGG Kesey

UGG Kesey

Best for – Keeping cozy while looking chic at the office or trudging through a case of the Mondays.
$159.95 + 9% Cash Back
Buy Now

While many may mourn the lost days of cute summer sandals in the dead of winter, we’re fully embracing the season of cozy feet with this selection of ten chic, casual ankle boots. While style is important, the unpredictable weather that the transition from fall to winter and through to spring months brings demands more out of your footwear than their fair-weather siblings. 

Our Active Junky team tested women’s boots against five universal attributes, and selected ten different models as our favorite ankle boots of the season. Our methods of testing were in line with how one would typically use these casual boots: during our day-to-day activities (but with a few adventures thrown in for good measure… this is Active Junky after all).

We consumed many a pint in the effort to find the best boots for brewery hopping. We waited to run our errands until the torrential downpour started in order to verify claims of water resistance. We sported them in the office to see which pairs didn’t get the side-eye from our bosses. We chose some of the more rugged of these boots for hikes in the Tetons, scoping out fishing streams in Oregon, and discovering waterfalls in Northern California. 

Brands Evaluated by Active Junky:

  • Ahnu
  • Columbia
  • Helly Hansen
  • Keen
  • Merrell
  • OluKai
  • Salomon
  • Teva
  • The North Face
  • UGG


Emily Applekamp

Questions To Ask Yourself

To guide you in your quest for the perfect boot, we’ve started with five big questions to ask yourself:

What kind of weather are you up against? 

Do you live in a climate where the weather is as moody as a 15-year-old, where what started out as a sunny fall day cruising downtown turns into a torrential downpour? If so, you should be looking at boots that are made of waterproof or water-resistant materials. Quality leather is a good start, but there are other features such as taped seams, Gore-Tex linings and water-resistant zippers that make the difference between dry feet and soggy socks.


Dan Rhodes

How much warmth and insulation do you need?

On that same topic, if your winter weather leans more towards blizzards than showers, you probably want to look for a boot that is insulated. There are many different types of insulation, from PrimaLoft to natural wool to proprietary insulation systems. Sometimes socks just don’t cut it and you need a little extra help to keep your toes toasty.

How much traction do you need? 

Are you hoping to wear your new kicks throughout winter? Will you be navigating icy sidewalks or wet pavement? Make sure to look for boots with a more aggressive tread and sole materials that brag about their slip resistance. Most brands offer their own proprietary sole material with varying degrees of tread.

What are you looking for in comfort? 

Do you want a boot that swaddles your feet in layers of cozy insulation, or are you looking for a structured boot that battles fatigue from being on your feet all day? Comfort is certainly a subjective thing, as our feet are all different shapes and sizes, but knowing what you expect out of the boot is a good start. Steel shanks and sturdy leather will give you more support, while soft suedes and cushy insoles will give you more of a slipper-like experience.


Dan Rhodes

How important is style? 

Sometimes, we just want a boot that performs as needed and other times we just want a boot that looks good. Style is personal preference, but there are certainly boots that lend themselves more towards office settings or date nights than navigating muddy trails. Features such as detailed stitching, decorative buckles or bright colors might be just what you are looking for to take your style up a notch.

How We Tested

The Active Junky crew leans more towards performance over style. That doesn’t mean we don’t want to look good, but it does mean we want to look good while still getting the most out of the attire and gear in which we invest and utilize. For each boot selected, and many others that didn’t pass muster, we selected a series of tests to make sure you are getting function as well as style.

A lot of our testing involved water. We subjected the boots to rain and shallow puddles galore that we all face during wetter months, but we also added immersion in ankle-deep creeks and bodies of water. We wanted to push the boots to their limits and find the break points.

Just as important as water resistance, we wanted to gauge comfort over time. While not every boot was taken onto a dirt trail, every boot saw a lot of miles.

We also made sure to test each boot over a variety of surfaces. We pushed the limits of each boot. Gauging purchase over slick rocks made for a few wet encounters, and attempting to slide over icy sidewalks may have resulted in a collision – or two – with the ground.

See how each boot measured up and additional testing we subjected the selected models to in the Field Notes included on individual product pages.


Dan Rhodes

Universal Attributes

Now that you have a better idea of what sort of casual boot you’re after via the questions above, it’s time to start whittling down your options. In the vein of those questions, we’ve outlined five major attributes we considered when testing and evaluating boots. We then selected one key attribute in which each boot excelled.

Comfort

Whether you are relaxing in a lodge or walking for hours on varied terrain, your feet should not be setting off any painful alarms.

Warmth

No one wants frozen toes during a snowstorm or sweaty feet during a warm autumnal stroll; we consider which boot is right for which climate.

Weather Protection

Wind, rain, puddles, and snow are not unique to times of adventure, so we test how each boot stands up to the elements.

Traction

Slipping is never pleasant. Sticking power helps mitigate injuries, improve performance, and avoid an embarrassing encounter with the ground.

Features

Some boots have that magical mixture of details that elevates them from just another pair of footwear to eye-catching accessories that make your entire ensemble. 

Women’s Casual Ankle Boots Reviews

The North Face Bridgeton Lace Leather The North Face Bridgeton Lace Leather

Editor’s Pick for Best Women’s Casual Boot

The North Face Bridgeton boots truly bridge the gap between fashion and function. The taller 8” shaft with seam-sealed construction allows you to venture into those deeper snowdrifts without worry of wet feet, but the weave detail and slight heel helps them land more on the side of chic rather than simply utilitarian. The soft suede and feminine detailing looks like it might fold under heavy conditions, but instead fights through situations that caused some burlier boots to fold.


Dan Rhodes

Tester Comment: “When the temperature drops and the rain starts to solidify into snow these boots find their sweet spot. PrimaLoft insulation combats the cold while the rich exterior materials are surprisingly resilient to moisture. Don’t let the softer styling fool you; these boots pack quite a punch in the performance department.”

Looking for more information about The North Face Bridgeton Lace Leather? Read the full review

Buying Options

9% Cash Back
$96.22
Before Cash Back
$87.57 After Cash Back
12% Cash Back
$174.95
Before Cash Back
$153.96 After Cash Back
5% Cash Back
$174.95
Before Cash Back
$166.21 After Cash Back
5% Cash Back
$175.00
Before Cash Back
$166.25 After Cash Back
Merrell Sugarbush Merrell Sugarbush

Best Trail-Ready Women’s Casual Boot

These Merrells pay homage to the outdoor lifestyle, but still bring a lot of comfort and style to the mix. Constructed of waterproof leather that is fully sealed, these women’s boots don’t let anything creep in even in the harshest conditions. Great traction, stiff construction, as well as mid-range cushion while walking, Merrell built a boot that pulls back just before you would call them hikers and delivers enough style to bridge the gap to street style.


Dan Rhodes

Tester Comment: “I wore these throughout a road trip of varied activity and intensity. They got a lot of looks from people who I am fairly certain had never seen a hiking trail, and they actually performed fairly well on hiking trails. The leather was easy to clean off between exploits, and any time I banged them up, it just added to their character.”

Looking for more information about Merrell Sugarbush? Read the full review

Buying Options

10% Cash Back
$179.99
Before Cash Back
$162.00 After Cash Back
Ahnu Chenery Ahnu Chenery

Best Street-Ready Women’s Boot

The Ahnu Chenery takes its inspiration from the footwear of woodland firefighters or burly lumberjacks, but gives it a feminine twist. Ahnu took many of the features from the Montara, one of their top-rated hikers and gave it a makeover that allows Chenery to fit seamlessly into an urban environment. Multiple textures, detailed stitching, and rich materials make these women’s boots a visual showstopper. Ahnu paid attention to detail for both performance and styling.


Dan Rhodes

Tester Comment: "These boots accompanied me for a long Oktoberfest pub crawl. The evening started out fairly warm but transitioned into a chilly night, which is right in Chenery’s element. My feet were comfortable pounding the sidewalk between pubs and cleaned up well after inevitable beer spills."

Looking for more information about Ahnu Chenery? Read the full review

Buying Options

10% Cash Back
$179.95
Before Cash Back
$161.96 After Cash Back
Columbia Women’s Cityside Fold Waterproof Boot Columbia Women’s Cityside Fold Waterproof Boot

The Columbia Cityside lives up to its name – it’s a perfect boot for spending a day pounding the pavement, particularly in questionable weather. Columbia took elements from their more technical lines and inserted them into a casual yet versatile boot. Suede and knit detailing add to the style, and strong traction and waterproofing make these great for when you’re looking for footwear that performs equally well on a dirt trail as they do on a sidewalk.


Dan Rhodes

Tester Comment: “I fall a lot. Some might call it clumsy, but I like to think of it as having a strong connection with the earth. The Cityside boots have amazing traction. I did not slip at all – not once! They did an amazing job of sticking to whatever surface I was traversing.”

Looking for more information about Columbia Women’s Cityside Fold Waterproof Boot? Read the full review

Buying Options

8% Cash Back
$94.90
Before Cash Back
$87.31 After Cash Back
11% Cash Back
$129.90
Before Cash Back
$115.62 After Cash Back
Helly Hansen W A.S.T 2 Helly Hansen W A.S.T 2

Ever wish your favorite tennis shoes could roll right into the wet winter months with you? Helly Hanson was nice enough to take all the things you love about sneakers and morph them into a boot. Lightweight and flexible while still warm and dry, these women’s boots are a unique entry into the market. The leather is waterproof, and while I wouldn’t stand in a pool of rushing water and expect to stay bone dry, they stand up really well to downpours and the occasional puddle jump.


Dan Rhodes

Tester Comment: “I recently took a trip to Jackson Hole. I walked the eight blocks into town to catch dinner and the night quickly evolved. These boots were extremely comfortable into the morning as I attended a mini country concert, danced for hours to a banjo sporting DJ, and walked back in the pouring rain while splashing through every single puddle.”

Looking for more information about Helly Hansen W A.S.T 2? Read the full review

Buying Options

Helly Hansen
0% Cash Back
$150.00
Before Cash Back
$150.00 After Cash Back
Keen Reisen Zip Full-Grain Waterproof Keen Reisen Zip Full-Grain Waterproof

The Reisens were meant to straddle the line between urban and outdoors. A slim design with well thought out features such as a stylish buckle detail helps these slide under the radar as “technical” boots, and passing as chic, casual kicks. These Keen women’s boots are insulated and waterproofed, plus an added reinforced toe protects against the occasional harsh kicks you purposely or accidentally might issue. Keen has created a great all-around boot that performs across functions.


Dan Rhodes

Tester Comment: “I took these on a weekend up at Lake Alamanor. They were comfortable and sturdy enough for hikes along the shore and through the woods. And when puttering around nearby towns or going to dinner, they were stylish enough to pair with dressier attire. I like the versatility and performance of these boots.”

Looking for more information about Keen Reisen Zip Full-Grain Waterproof? Read the full review

Buying Options

12% Cash Back
$159.95
Before Cash Back
$140.76 After Cash Back
OluKai Nani Kamea OluKai Nani Kamea

The Nani Kameas, while having natural water-resistance with their premium, full-grain leather construction, are ones you’ll think twice about throwing on in gnarly weather, mostly because they’re just so pretty. With a timeless style, these boots work equally well with jeans as they do with a flirty floral-print dress. Classic style with the perks of modern technology, these boots are an homage back to a simpler time, but without the pesky task of actually working on a prairie.


Dan Rhodes

Tester Comment: “These boots were pretty stiff right out of the box, but within a couple of wears, they softened up to be a really comfortable, dressy boot. I appreciate the attention to detail, such as the traction pads on the sole, and the footbed with different densities for optimal support. While they may look like your standard nice leather boot, they clearly have a lot of thought behind them."

Looking for more information about OluKai Nani Kamea? Read the full review

Buying Options

10% Cash Back
$259.95
Before Cash Back
$233.96 After Cash Back
Salomon Hime Mid LTR CSWP Salomon Hime Mid LTR CSWP

The Salomon Hime is a high-functioning winter boot that has tons of features to kick the style up a notch (or 10). Using “full bootie” construction, Salomon has built up a waterproof winter boot and given it additional features to combat snow and ice. Using an ice grip rubber compound, they latch onto the ground even through slick icy conditions. Plus there is a bevy of features to help keep the cold out and the warmth in.


Dan Rhodes

Tester Comment: “These Salomons are totally up for the snow. They were crazy warm and very comfortable on a meandering hike through the white stuff. My feet stayed dry and warm, while my fingers did not fare as well due to forgetting my gloves. I felt sturdy walking on the slicker ice as well as in the deeper fluff.”

Looking for more information about Salomon Hime Mid LTR CSWP? Read the full review

Buying Options

6% Cash Back
$102.00
Before Cash Back
$95.88 After Cash Back
15% Cash Back
$139.95
Before Cash Back
$118.96 After Cash Back
7% Cash Back
$160.00
Before Cash Back
$148.80 After Cash Back
9% Cash Back
$189.95
Before Cash Back
$172.86 After Cash Back
Teva De La Vina Low Teva De La Vina Low

Sleek styling and sturdy construction, these boots perform just as tough as they look. While Teva is most known for their less-is-more water sandals, they have been increasingly delivering quality footwear in other categories. Case in point, the De La Vina line of boots that boast high quality materials, solid design elements, and the technical perks necessary to compete in the realm of rugged winter boots. The De La Vina Lows are great ankle boots with a bit of an edge.


Dan Rhodes

Tester Comment: “Teva and rebel are not words I would naturally equate with each other, but I’ll say it – these Tevas make me feel pretty rebellious! Whether it is the kind of rebellion where you hop on a motorcycle or blaze a trail, these boots will be able to keep up.”

Looking for more information about Teva De La Vina Low? Read the full review

Buying Options

12% Cash Back
$139.95
Before Cash Back
$123.16 After Cash Back
9% Cash Back
$139.95
Before Cash Back
$127.36 After Cash Back
4% Cash Back
$140.00
Before Cash Back
$134.40 After Cash Back
4% Cash Back
$140.00
Before Cash Back
$134.40 After Cash Back
UGG Kesey UGG Kesey

UGG is known for its classic boot that basically looks like a super plush and comfortable slipper built up to boot height, and tweaking it just enough to exist as footwear suitable for public consumption. The UGG Kesey women’s boot is the next iteration in the evolution of that undertaking. It not only passes as fashionable footwear, but excels in style and performance. It melds a huge amount of comfort with weather protection, and dresses up your winter wardrobe.


Dan Rhodes

Tester Comment: “You know those days when you just want to lounge around in your slippers, but you need to leave the house for ridiculous reasons, such as I can’t continue to eat only peanut butter from the jar, or I have to go to work so I can continue to pay my mortgage? The UGG Kesey is the perfect boot for those days – they feel like you are still in house slippers, but you look like you are properly adulting.”

Looking for more information about UGG Kesey? Read the full review

Buying Options

9% Cash Back
$159.95
Before Cash Back
$145.56 After Cash Back
7% Cash Back
$160.00
Before Cash Back
$148.80 After Cash Back
6% Cash Back
$160.00
Before Cash Back
$150.40 After Cash Back