The Fall Edit: Ankle Boots

Two outfits with classic ankle boots. Details at une femme d'un certain age.Ankle boots still reign supreme in my footwear wardrobe. They’re an essential part of my style formula, and every fall I look forward to building outfits around them again. They work well for cooler season travel wardrobes (and even some warmer season ones). I find them to be comfortable and supportive too.

While I’m wary of flogging trends, what I’ve found is that sometimes today’s “trend” becomes tomorrow’s “classic.” Ankle boots (like skinny jeans) started out as a trend, but have become a perennial. Above, a couple of higher end ankle boot styles that started out as “It” pieces a few years ago and are still going strong:

Left | Right

Ankle Boots: My Fall Picks

Here are a few more styles that feel both classic and current.

Western

Donna Karan western-style bootie. Details at une femme d'un certain age.Though Western-inspired boots are “on trend” this fall, I think if you avoid a very literal or costume-y interpretation, this will be a style with some staying power. (Unless, of course, actual cowboy boots are a regular part of your wardrobe. In that case, go for the real deal and have fun!) Above: The shape may hint at “cowboy” but these have a very sleek and urban 90’s vibe.

Brown suede western-inspired ankle boots. Details at une femme d'un certain age.

That heel looks higher in this image than it does in person. These suede booties lean a little more Boho and would work with either jeans or a longer skirt or dress. (Also available in black leather.)

Animal Print

J.Crew snake print ankle boots. Details at une femme d'un certain age.

I’ve shared a few leopard print options here, here, and here. Reptile prints are also popular this fall. The low heel and rounded toe on this pair temper the edginess of the snake print.

Modern Classic

Everlane Day Boot ankle boots. Details at une femme d'un certain age.

Simple, elegant, and VERY comfortable, this style is offered in several colors. Lovely soft leather, and they run true-to-size.

Black kitten heel ankle boots with side zip. Details at une femme d'un certain age.

Kitten heels have been trending for the last few seasons, and can be another comfortable option for those who prefer a more feminine look. This style is available in Regular and Wide widths, and seems to be well reviewed for comfort.

Sock bootie in wine fabric. Details at une femme d'un certain age.

Reader Susan asked about an option for those with thin legs who want a closer-fitting shaft. Sock booties like this one have also been trending the last couple of seasons. They usually feature a fabric or stretch suede shaft that hugs the leg. Very sleek!

Weatherproof

Aquatalia weatherproof ankle boot in espresso. Details at une femme d'un certain age.

Whether in Espresso (shown) or black, this weatherproof Chelsea boot could be a great dress-up/dress-down travel wardrobe option.

Blondo weatherproof ankle boot in black nubuck. Details at une femme d'un certain age.

More budget-friendly, this style is offered in several colors and in Wide widths as well as Medium. Another style with lots of great customer reviews.

Aquatalia Ulyssa weatherproof ankle boots. Details at une femme d'un certain age.Did someone say navy? This low-heeled style is offered in black, brown and navy suede, and yes, that suede is weatherproof! I’ve tried these on and they’re very comfortable, not too narrow either.

What ankle boot styles do you wear most often?

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45 Comments

  1. Nancy
    October 2, 2018 / 3:35 am

    I may have…99.9% chance this is true…the worlds worst feet…Plantar fasciitis, Freibergs , etc etc…so if I find these boots work, ..almost anyone will…The Valli by Blondo that you recommended. They are great for work; stylish and comfortable.

    I wish they had removable insoles so I could put in my custom orthotics for long distance walking.

    If anyone has any suggestions for boots or booties for bad feet that have both removable insoles and come in wide width , please share.

    I did buy my first pair of Mephistos this past summer and altho they are reg. width, my orthotics fit so considering a pair of their boots/booties but so expensive…would love any specific recommendations for this brand. Thanks in advance.

    • Meg
      October 2, 2018 / 4:23 am

      Vionic- you can take out the footbed and they are available in wide.

      I learned after a marathon of trying on booties, I need at least a 6″ high boot. The low ones all drive me crazy bumping on my ankle. So I did find an EF bootie, with a modified kitten heel in a black knit. Super comfy and very sleek looking.

    • Liz in Paris
      October 2, 2018 / 10:18 am

      Not sure where you’re based but the German brands Gabor and Ara have a selection of reasonably chic/trendy shoes in G (slight extra width) and H (generous extra width), some with removable insoles. I often buy them on Amazon so you could try there. They’re a bit less expensive than Mephisto too.

    • Amy
      October 5, 2018 / 6:16 pm

      I have foot problems and wear custom orthotics, too, and I know how hard it is to find boots that have enough space in the toes and insteps! My orthotics fit well in the Naot “Helm” style of ankle boots when I remove the insoles. I have them in two colors now! I’m not sure whether they come in wide, but it might be worth a look. Good luck on your hunt!

  2. Mimi
    October 2, 2018 / 4:14 am

    There is no link to the snake skinned bootie, could you send it? Thanks

  3. Canada
    October 2, 2018 / 4:26 am

    Love my ankle boots! I’m only 5’2″ so I usually wear black booties with dark rinse jeans to maintain a column of color on the lower part of my body. I’ve just returned from Paris where the weather was cool in the mornings but then hit the 70’s by early afternoon and so street fashion was all over the spectrum. Tho booties, with high and low shafts, sleek or carting lots of hardware, flat or chunky higher heels, were everywhere. Along with sneakers. Ballerina flats seem to be fading.

    • Liz in Paris
      October 2, 2018 / 10:22 am

      I agree, I live in Paris and have noticed that ballerinas seem to have had their day, both on women and in the shops. There are a lot of sandals and sneakers in summer, boots and sneakers in winter, and a mix in spring/autumn.

  4. Susan
    October 2, 2018 / 4:52 am

    Help! Does anyone have suggestions for booties for thinner legs? I wear a 10, and by the time most booties get to my size, the circumference around the top is so big that I look like I’m standing in buckets! I haven’t found a brand that works, and I’m excited to jump on this style trend.

    • Laurie
      October 2, 2018 / 5:20 am

      I love my ankle boots! It’s still sandal season in Northern Virginia but looking forward to boot season soon. I have three pair of ankle boots – all the Munro brand. They have removable inserts, are super comfortable and come in a variety of widths. Munro has a new boot this year that kind of looks like a doc Martin or work boot. It’s super lightweight! I’m thinking about getting it but have no idea how I’d style it.

    • Susan B
      Author
      October 2, 2018 / 7:02 am

      Hi Susan, have you tried a “sock” ankle boot like this one? http://shopstyle.it/l/S1jv They seem to be designed to hug the ankle and leg.

      • Susan
        October 3, 2018 / 5:45 am

        Thanks so much, Susan! Good suggestion. I hadn’t seen these. I’ll give them a try.

  5. Kate LILLICH
    October 2, 2018 / 5:13 am

    Susan, do you have shopping details for beige cardigan in pic on left? Thx, kate

  6. Amy
    October 2, 2018 / 5:15 am

    Regarding the request for booties with removable insoles, Munro makes comfortable shoes and booties in a broad range of sizes and most have removable insoles. Nordstrom and Zappos are two of many outlets for their products; the company website is munroshoes.com.

    • Pamela
      October 2, 2018 / 5:19 am

      I’m a big fan of Munro because their shoes actually fit my AAAA width feet. Their Robyn boot is similar to some of the styles above and takes orthotics.

    • Nancy
      October 2, 2018 / 7:02 am

      I have several pairs of Munro shoes/boots. and like them…..was looking for another option for some variety.

  7. October 2, 2018 / 5:19 am

    Still wearing my Dickers! Also the waterproof brand you turned me on to, Aquatalia.

  8. Vivien
    October 2, 2018 / 6:06 am

    Ron White has a number of great booties-you can take the insole out. Comfortable and weatherproof. Canadian designer. His website has list of sellers. Once a year he is shown on The Shopping Channel.ca-sells out most sizes in minutes. Not inexpensive but very good quality. I find his almond toe shoes fit half size small but boots are true to size as toe box is more generous. Always timeless, classic styles with a twist.

    • Nancy
      October 2, 2018 / 6:11 am

      do you have “fussy feet’? I ask because then you understand how much I need the orthotics for long distance walking and how hard it is to find stylish shoes with good arch support that allow me to use them. Good to know that the boots run larger in toe box

  9. Kristen Oxwang
    October 2, 2018 / 6:11 am

    Is there a link for the reptile booties? I’m having to (hopefully temporarily) revamp my footwear collection after hip surgery and am on the prowl for lower heels that have a little pizazz. These are perfect!

      • Kristen
        October 2, 2018 / 6:36 am

        Merci!

  10. October 2, 2018 / 6:31 am

    I’m a big fan of ankle boots and have many. This year I did buy very streamlined Western versions in both black leather and cognac suede. It’s just a little tweak to stay a bit trendy.

    • Carol
      October 2, 2018 / 7:08 am

      Tell me about your cognac suede. I’m having trouble finding the perfect cognac boots.

  11. Jeanne J
    October 2, 2018 / 7:00 am

    Another vote for Munro, in terms of comfort and fit. I bought the suede Munro Elessa bootie, at the Anniversary Sale, I think. It’s been too warm to wear it yet, though! I too appreciate Munro’s removable insoles, and the steel shanks are very supportive.

  12. Marguerite Krenek
    October 2, 2018 / 7:44 am

    I am an ankle bootie devotee, as I have nine pair I wear every fall and winter. My favorite brands are Paul Green, Aquatalia, Munro and Dansko. I troll 6 p.m. com all year long looking for bargains.

  13. spacegeek
    October 2, 2018 / 9:29 am

    Thoughts on ankle booties with dresses? I am a fan of the midi (hate my knees) and as a shorter (5’4″) person, I have always preferred tall boots with dresses to avoid breaking up the line too much. But tall boots seem to come mostly in OTK styles these days (that’s a lot of boot–see short person comment) or booties.

    Some of my older tall boots need replacement, but I’m not talking flat riding boot styles but rather heeled tall boots able to pair with a dress. That seems to be harder to find right now.

    • Susan B
      Author
      October 2, 2018 / 10:11 am

      I think ankle boots can look great with skirts and dresses. I find that wearing tights that match either the skirt or boot color helps avoid a more broken up look.

  14. October 2, 2018 / 9:32 am

    I’d like to plop my head on the top outfit on the left–ha ha! I’ll check out the link and see if I can emulate the look.

  15. October 2, 2018 / 9:49 am

    I have a pair similar to your second-to-last pair and they have been so great. A good shape, neither cowboy (which is not my style at all) nor with heels too high to walk in. I love Chelsea boots, too.

  16. Katie
    October 2, 2018 / 10:29 am

    I find the Blondo Valli to be extremely comfortable, and the fact that they are waterproof make them ideal for Seattle. And ideal for travel, from cobblestone walks to evening dining. I now have four pair; – black suede, black nubuck, cognac nubuck , and mushroom (a color I can’t seem to style very well). The taupe seems dull with black or navy. Suggestions?

    • Nancy
      October 2, 2018 / 10:53 am

      Hi Katie- as I said in earlier post, I also have been very happy with the Blondo Valli. I wear alot of dark colors., espec. on the bottom so black tights are my “go to” in the winter…what color do you find besides black that you wear the most? Considering a second pair of these booties and I now own black suede.

  17. Connie Miller
    October 2, 2018 / 10:30 am

    Susan, regarding the current pant/shoe mating trend, I am seeing mostly skinny pants or long skirts with bare ankles showing above ankle boots. It looks good on the models but being 5′ tall, I find the break in column color makes me look even shorter. Would you do a post on pant/shoe/boot/hems for us? Thanks in advance!!

    • Paula
      October 19, 2018 / 7:32 am

      Susan – yes, this would be super helpful!

  18. Allie
    October 2, 2018 / 3:09 pm

    Is it just me, or does anyone else think ‘Oliver Twist’ when they see the “ankle boot not quite meeting the bottom of the pants” thing? That, and it makes one look shorter, IMO?

    • Nancy
      October 2, 2018 / 4:01 pm

      I wore ankle pants and booties today and have to say…altho I like often the “look” on others, not sure its flattering on me…my legs do look shorter…and heavier I think because its not one clean straight line.

      • Melanie
        October 3, 2018 / 2:04 am

        I find that if my pants are more slim-fitting (as opposed to a wider-cropped fit, but not skin-tight like leggings) this look is more flattering on me. I’m almost 5’4 and am always looking for ways to appear more ‘streamlined’…

    • Susan Bowdler
      October 2, 2018 / 11:28 pm

      Definitely! Cannot get on with ankle boots at all. They rub my ankle bone, make my legs look shorter and the gap looks odd. Can’t like everything I guess!

      • NaNCY
        October 3, 2018 / 2:54 am

        I wear booties with dresses/skirts (with same color tights) and full length pants, its just with ankle pants that I am not fond of the look.

  19. Diane
    October 2, 2018 / 4:20 pm

    I ordered the Blondo and a pair of Naturalizer boots to see which was most comfortable. I wear a 71/2 wide and have to have orthotic insoles so I ordered 8’s in both to be sure to have enough room. I am also wearing ankle support now. Both pairs fit in the 8?wide but the Naturalizers were more comfortable. Both are waterproof, so I decided to keep the Naturalizers. They are pretty supportive and I’m planning to wear them in Italy later this month on a sightseeing trip.

  20. Jill
    October 3, 2018 / 6:14 am

    Just saw where Kate Middleton brought out her 14 year old riding boots…. Maybe we’ll all be talking about them next year-lol!

    • Susan B
      Author
      October 3, 2018 / 7:15 am

      I’ve been looking to update my old riding boots for a few years now…so I’m hoping so too!

  21. MARLA
    October 3, 2018 / 2:49 pm

    LOVE my new Rebecca Minkoff leopard print flat booties. $200 investment but well worth it!! Love the blog!

  22. Linda
    October 4, 2018 / 12:12 am

    Sadly, winters are way too cold where I live to manage that little exposed-skin gap between boot and pant hem (I love the look). We have only a few weeks in late September/early October to get away with that. Can wear them with dresses and leggings or tights, but I find myself wearing dresses less often. It’s hard to be stylish during northern winters! 🙂

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