How to Wear Ankle Boots With Skinny Jeans, Leggings, or Shorts – Tips for Older Women
by Tina Boomerina (Christina Gregoire)
I can show you tips about how to wear ankle boots with leggings, jeggings, skinny jeans, dresses and, possibly, shorts. Short boots for women are fun and versatile.
Note: This article has been updated to reflect changing fashion trends.
High Heel Ankle Boots for Women
Let’s start off with a disclaimer. I only wear heels. Unless I’m off to the dog park or on vacation, I’m probably wearing high heels, so I know more about stilettos and stacks and platforms and blocks and kittens and wedges than I do about flats. The last time I wore flat ankle boots was during new wave (1980s), when Oingo Boingo was on the radio and I was pregnant. But, even though most of my experience is with high-heel ankle boots and short-heel ankle boots, the same rules should apply.
Important: "Rule" is probably the wrong word. The following fashion rules are only guidelines, as there are usually exceptions to every rule. You are the artist of your own wardrobe. Be creative.
Best Ankle Boots for Skinny Jeans and Leggings
I prefer any type of high-heel boot to most high-heel shoes because a boot with the right fit will stabilize my ankle. This makes boots and booties easier to walk in than pumps or high-heel sandals.
Most Women Tuck Their Jeans into their Boots
In my opinion, ankle boots look fabulous with skinny jeans and leggings, as long as the jeans or leggings are tucked into the ankle boot. That's how I wear this look.
However, things have changed since I wrote this article way back in 2011. These days, many fashionable chicks... dare I say chic hipster chicks with excellent taste... are wearing their skinny jeans a tiny bit shorter by rolling up the hem about half an inch or maybe an inch.
I have a feeling I should take the word hipster out of this article, because some people don't like being labeled with that classification. I like the word "hipster". To me, it just means a person who is hip to the current, modern trends worn by the hippest of hip people. I know hipster describes a specific fashion and lifestyle... but... the word hipster just rolls off the tongue and makes me smile.
Someday I will try to explain the hipster style as I see it.
Rolled up Jeans Are Not Tucked into Ankle Boots
If you are wearing cropped pants or rolled-up (cuffed) jeans, you will not be able to tuck your trousers into your booties. Trendy women are wearing ankle boots and skinny jeans with a small gap between the pants and the boots. I don't do that, but it is not wrong to wear your jeans and boots in this manner.
For most of you, your booties should be the same color or the same shade (same darkness) as your jeans or leggings. That's what I usually do because I have short legs, and this gives the leg a long, unbroken line. And, in my opinion, cropped pants with ankle boots only look good on women with very long legs. (I don't mean a gap of half an inch, I mean short crops.)
Not Everyone Can Wear Catwalk Styles
Most of our fashion faux pas stem from seeing a trend on a tall, catwalk model and thinking it will look good on a regular woman like you or me. However, most females are not anorexic and 6 feet tall.
Short Boots and Boot Cut Jeans
Modern ankle boots were originally designed to be worn under trousers, because knee-high boots interfered with the silhouette of a woman's pants. So, flat ankle boots and high-heeled ankle boots are perfect for wearing with all straight-leg, flared, or boot-cut jeans and trousers.
If your pants are wide enough to fit easily over your boots, you can do whatever feels most comfortable. However, I prefer the artsy look of skinny jeans tucked into boots.
How to Wear Ankle Boots With Dresses
It’s a little tricky to wear ankle boots with a short dress, so here are my rules. If you are over 40 or 45, you'll probably want to follow these rules at first. After you get into the look, you can try other things.
- Dark legs look best with dark booties. Bare legs look best with nude booties. There are exceptions, but these are the rules. Once you get the balance down, you can break the rules to go with your mood.
- This is the wrong way to wear ankle boots. Ellen Page should wear a dress with a flared skirt to balance her shoulders. And, these dark booties look strange with that dress. Light brown boots would be better, although Ms Page would look beautiful wearing a trash bag.
Can You Wear Ankle Boots With Shorts?
Normally, I would snicker if I ever saw a female wearing ankle boots with shorts, but I have seen teens wearing shorts with chunky-heeled boots and they pulled it off.
Call it hipster style, call it festival style, or call it hot pants redux, but whatever you want to call it, outfits involving shorts are more prevalent now than when I first wrote this article.
For ladies over 40, you can wear city shorts in place of a short skirt, although you should avoid regular shorts (and denim cut-offs) once you reach true "adulthood". I don't care how hot it gets. And, if you ever wear stilettos with shorts, your friendly neighborhood hookers will stop and tell you that you have no taste.
Update: Yes, it's fine for all of you young hipsters to wear cut-off jean shorts. Just don't let your moms borrow them.
Maxi Skirts With Ankle Booties
Both flat and high-heeled ankle boots are great with long skirts. I believe you should wear tights to match the boots, if the boots are dark, because when you sit down more of your leg will show. One alternative would be to wear cute funky socks with a Fair Isle (Nordic) or repeating pattern. People would only get a glimpse of this chic little detail.
My new favorite thing is to wear my ankle boots with funky patterned socks, but I scrunch the socks down so they hardly show... like just an inch or two. Very fun. I'm losing it in my old age, but I'm losing it in a subtle way that doesn't make people want to run away from me.
Cuffed Ankle Boots
Cuffed booties can be worn with leggings, skirts, and shorts. The most important thing with cuffs is that you must be able to see the contrast of the wide cuff against the skinny leg. Cuffed boots are only cute if your skinny leg (or covered skinny leg) shows. Without that, your ankle boots will appear clunky.
For an easy no-brainer, tuck your skinny jeans into your cuffed boots. I think that cuffed boots are super sexy if they are done right. And, some cuffed boots look better if they contrast with the jeans or leggings.
All women should start their own fashion experiments in front of their mirrors and try their boots in new ways. I started wearing black suede booties with black tights in 1997. I remember this because '97 was an important year for me, and I remember my girlfriend saying, “I didn’t know you could wear ankle boots with a mini skirt.” Right. Like I needed permission to wear my own clothes.
Any woman can look amazing in ankle booties, but every woman looks best in her own adaptation. When you get a pair of booties, try them on with everything you own. As long as you have a full-length mirror, you will be able to tell what works best with your type of body.
More Articles for Hip Baby Boomer Women:
Photo Credits: prshots.com.
- Main Photo: I lost the list for these boots when we updated the site.
- Wedge Ankle Boots: Monsoon.
- How to Wear Ankle Boots With Skinny Jeans: Monsoon.
- How to Wear Ankle Boots: Miss Self ridge.
- Ankle Boots Are Fun & Sexy: Apricot, Phase Eight, East.
- Pattern Socks: White Stuff.
- Short High Heeled Boots: Hobbs.
- How to Wear Ankle Boots: La Redoute.com.
What Do You Think of this article? Leave a comment at the bottom of the page. I need to write an article about cuffed jeans... someday... but I'll have to study younger women because I don't wear that style.