If you’ve ever put a pair of ankle boots on with a dress and wondered if they look right.  Or have stood in front of the mirror not knowing whether you should tuck your jeans into your boots, or pull them over the top, this post is for you!  It's absolutely bursting with information about how to wear ankle boots and what style of ankle boots goes best with the autumn winter 2020 fashion trends, so you know exactly what style of boots to wear with your outfits, and how to wear them!

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It’s a good idea to take both your shape and your outfits into consideration when you’re choosing an ankle boot, otherwise you could end up wasting money on booties that don’t look good on you, and don’t work with your outfits.

These 6 tips will help you choose the most flattering ankle booties for your shape, and the best style for your outfits:


The point at which the top of the ankle boot hits your leg will affect how flattering they are.  The general rule is that the most flattering height of boot is one that cuts you across a narrower part of your leg. The reason being that the top of the boot will draw a line across your leg, so if it does this at a narrow point your legs will look slim, and if it draws a line around a wider point, your legs will look wider.  So, choose a pair that highlights the point you want to show off!

A couple of other points to note are that:

  • Tall ankle boots will help to elongate the legs and they make a great option if you’re wearing a cropped jean or pant and you don’t want a gap
  • And short ankle heights can shorten the legs, but they do sit well with longer, tighter fitting pants or jeans.


Ankle boots with a narrow ankle can slim and lengthen legs.  Styles that hug the leg are a great option to go for if you want to wear jeans or pants that are cropped or wide as they sit beautifully underneath the ankle of the jeans.  And they always look chic with skirts and dresses.

  • Ankle boots with a wider ankle are a great way to make a wide ankle look slimmer
  • On the other hand, if you have very slim ankles a wide cut bootie may emphasize your narrow ankles and end up looking quite clumpy on you, especially if you’re wearing them with dresses or skirts.
  • Wide cut ankle booties are the best style to go for if you like wearing skinny jeans as you can easily tuck the hem of the jeans into the ankle of the boot


A pointed toe boot will elongate the leg, making it appear longer and narrower, where as a square or round toe may shorten your leg.


A mid to high heel will slim and lengthen your legs, while a flat boot will shorten you.


A slim, kitten or stiletto heel often looks a little squashed on women who carry their weight on the bottom half. A chunky, block heel will be much more flattering.  And if you have slim legs then a chunky heel can emphasize slimness and can look a little clumpy. A slim heel will balance your frame much better


Take my quick quiz to find out which of the primary body types best aligns with yours, so you can start dressing to make the most of it!


Is it better to tuck jeans or pants into booties, or leave them un-tucked?

If your jeans fit neatly inside the ankle, then tuck them in.
If the jeans bulge out the top of the boots when you tuck them in, I suggest you either:

  • Cuff your jeans so they’re just sitting above the top of the boots. You can do a small cuff or a wide cuff, it can be neat or messy, whichever you prefer…or whichever is needed to get the length just right.
  • Or, (this one may seem a little more drastic) you could chop the hem of your jeans so they sit at the right length. You don’t need to do anything fancy with the hem, you can leave it raw. I’ve done this to a couple of my skinny jeans and I love the look.

Is it OK to stretch my jeans over the top of my booties?

I always think this looks a little odd, especially if the jeans are so tight that you can see see the silhouette of the booties through them then.  You’ll also probably find the jeans ride up over the top of the boots.  I suggest cuffing them so they sit above the boots, of choose a style of boots with a wider ankle so the jeans can be tucked inside them.

What style of ankle boots work with with cropped jeans and pant?

An ankle boot that has a narrow ankle that hugs your leg will be the best style, and I also suggest one that’s tall enough to sit under the leg of the jeans so you don’t have a gap to deal with.  I’ve shared my favorite booties to wear with cropped jeans below, so just scroll down to see them, or click HERE.

How should I cuff my jeans?

  • You can roll them – this works best if you only have a small amount of fabric that needs turning up. If you have a lot to roll it can end up looking like you’ve a sausage around your ankle
  • You can do a narrow cuff
  • You can do a wide cuff – this is great if the jeans are very long, but be mindful that a wide cuff can sometimes shorten the leg, so have a play around and see what works best for you and your shape.
  • And you can do a messy cuff – this is another good one to do if you have a lot of fabric to turn up.

What do you do about that gap between the hem of your pants and the top of your booties?!

If it’s not too cold I suggest simply leaving it bare or wearing fishnets, but if it’s too cold to be barring any flesh you have a few options:

  • Wear a colored or patterned sock or tights – metallic’s look great as do polka dots!
  • Wear socks or tights in the same color as the boots to create a column of color that elongates


You will probably find that you need a couple of different styles of boot; one to go with dresses and skirts and a second to wear with jeans and pants.  I wear tight ankle boots with skirts, dresses and cropped pants and a wider, more casual, style with jeans, because that is what suits me the best.  I recommend that you experiment a little and see what works best for you.

  1. If your ankle boots aren’t quite wide enough to tuck your jeans in (or for them to remain tucked in after you’ve walked a bit) then roll the hem of your jeans so they sit just above the top of the boot.
  2. For some pretty brilliant leg lengthening, match the color of your boots to the tights your wearing.
  3. Wear them with cropped pants.  I prefer to wear a heeled boot with cropped pants as I find it more flattering but if you have long legs then a flat boot will look chic, too.
  4. Wear pants with a zipper at the ankle.
  5. Tuck your jeans in to a pair of socks
  6. If the ankle boot is wide enough and your pants narrow enough, simple tuck them in.
  7.  If you want a more relaxed, ‘I just threw this on as I was running out of the house’ kind of look then try the half cuff.
  8. Go bare legged
  9. The trend for cropped frayed denim isn’t to everyone’s taste, but it is a great trend to pair with ankle boots.  If paying for jeans that are already ripped and frayed just seem like madness to you, then you could always test it out by cropping and fraying an old pair of jeans.
  10. Wear them under flares
  11. Wear them with a maxi.
  12. Wear them with a pair of tights in a contrasting color.

The best ankle boots and booties to wear with skirts and dresses in 2020

  • A tight ankle will be the most streamlined and so will be the most flattering. It will elongate and slim your leg, especially if it’s healed boot
  • A wider ankle also works, but watch where it cuts your leg, if it cuts across a wider part of your leg it will be less flattering
  • Pointy styles always look great as they elongate and slim the legs

The best ankle boots and booties to wear with skinny jeans in 2020

  • A wider ankle will enable you to tuck your jeans into the boots without them bulging or getting stuck
  • A pointy style will elongate and narrow your leg
  • And a lower shaft height will prevent you from needing to cuff your jeans a lot

The best ankle boots and booties to wear with cropped jeans in 2020

  • A tighter fitting ankle will work best so that the cropped pants can layer comfortable over the top
  • A tighter fit will also help to narrow and elongate your leg which is a great way to balance out the extra width that the wide leg gives you.


The best ankle boots and booties to wear with straight leg and wide leg jeans in 2020

  • A tighter fitting ankle will work best so that the jeans can sit comfortably over the top of the boots
  • Many straight leg jeans are ankle length, so a low rise pair of ankle boots will work well.


The best ankle boots and booties to wear with flares in 2020

  • A heel is often he most flattering boot style with a flare as it elongates your legs…flares are often longer than most jeans styles so they need a little extra height.
  • Platforms are always a winner with a flare
  • And a pointy toe gives them some rock and roll edge


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