3 Stylish Ways to Wear Ankle Booties

Something as simple as a new pair of booties can kick up your wardrobe and give you a lift. Here’s a look at three popular bootie styles and what to wear them with.
Booties - Casual Weekend Jeans

1. Get Modern in Perforated Booties

Taupe nubuck booties with perforated panels add a beautiful shot of texture and create a minimalist modern vibe.

They’re especially great for transition times like winter to spring when you want something lighter and airier, but you still need to cover your toes. Wear them with jeans and a pretty lace-up sweater for a fab weekend look.


2. Go Wild in Western Booties

Cowboy booties are one of the most popular styles out there. Here’s a pair that’s a little different from your basic suede variety.  Handpick stitched wraparound straps add beautiful detail to this attractive leather bootie that looks fabulous worn with straight or boot-cut jeans.

A color-blocked sweater coat in earthy tones complements the rich whiskey color. A soft saddlebag works with the easy vibe, and a little jewelry finishes off this modern-day western look.


3. Be Edgy in Biker Booties

If you like an edge and have an inner rock-and-roll chick side to you, then you’ll be right at home with a pair of moto booties. Biker booties boots are black, sturdy, no fuss, and a little tough.

To balance the hard edge, try a soft, pretty cold shoulder sweater. This touch of feminity paired with the rough and tough bootie nails the trend without making you look like a biker.

More interested in evening booties? Here are some ideas for how to wear dressy booties on a night out.


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13 thoughts on “3 Stylish Ways to Wear Ankle Booties

  1. Great post! I just wore my booties this week to work. I took a look from your Nov 28 post with the cape and added my skinny jeans rolled up a bit along with a “past the hips” length top. The age-appropriate top and poncho turned the look to sophisticated instead of “millennial.” I have a 24-year-old daughter who wears booties, so I’m familiar with the “millennial ” look very well!

  2. I am happy with how I rated the questionnaire. I discovered one thing – that I am not up-to-date on my purses. I will buy a more modern style when looking for a new bag. I also found that cashmere button-down front sweaters are not the thing to wear. They make a person look heavier. However, considering I look about 25-30 years younger than my age, I agree. I am a person who has always had many allergies. I spent very little of my life in the sun. I believe this is one of the reasons I look a lot younger than my age. I have always been interested in clothes and checking out current styles. I don’t feel I am dressing “too young” for my age. Thank you for giving me the quiz to take. It is very kind of you.

  3. With a young-looking face and body, I get attention from men 20 years younger. The problem is I’m 69 and dress conservatively. At 69, heels are out of the question with foot problems. The booties are adorable but not practical in Colorado. Denim is the uniform of the day out here. I love to dress classy, but living in an old building surrounded by 70-80 year-olds with no sense of style is a challenge. How is one to dress classy in the snow? I love your column.

  4. I love these boots but am not sure how to wear them. Do you tuck your pants into them or wear boot cuts on the outside? If you carry more weight in the top, how do you balance it with skinny jeans tucked into boots? Pics would be fantastic!

    1. Hi Deb, the key is to show off the entire bootie. (Don’t wear your pants long and untucked, so they cover part of the bootie.) For skinny jeans and leggings, tuck in. For straight-leg or boyfriend jeans, roll up and cuff so there is a hint of ankle showing between the cuff and bootie. Bootcut or flare jeans won’t work with a bootie. To balance up top, choose a v-neck or scoop neck top to show off some skin and create a slimming line. Amy high neck top like a crew neck or turtleneck will only make you look heavier if you are already big up top. I hope that helps! Cheers, Deborah

  5. I was excited to see this post because booties are on my wish list! I would like to see some examples of ways to wear them – the bottom of the pants covering the top of the booties, rolled up pant hem, visible bootie socks, etc. I love some of the looks I’ve seen, but at 59, I don’t want to look like I’m trying to pass for 28.

  6. I find such enjoyment in your postings. It is so difficult to find stylish advice for us ladies over 40. I am a young 53-year-old who has always enjoyed fashion, yet as time went on….the fashion industry seemed to forget we existed! Thank you for sharing your sense of style and proving we still “wear it well.”

  7. I love the boots, but I don’t know if I’d be brave enough to wear them! Another problem is that NZ is such a casual culture dress-wise that I tend to slide into the tracksuit every, day type of uniform…

  8. Very cute! And I don’t wear heels anymore, so I’m glad there are such friendly alternatives! I mentioned your blog in my post this morning! I wanted everyone to know about it, and you, sweet lady! ♥

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