How To Wear Ankle Boots With Different Outfits

Written by , MSc Pratima Ati MSc
Last Updated on

What If I tell you that you can wear boots with any outfit and look fabulous? Would you trust me? Well, just keep reading, and you surely will. There is so much more you can do than just pair them with your denim (and denim alone).

There are a ton of varieties out there and endless ways to flaunt your boots, so I’ve tried to round off a list with the most popular outfit ideas and how you can style those seasonal boots.

How To Wear Ankle Boots With Outfits – 12 Best Ways

1. How To Wear Boots With Jeans?

A combination that is a staple with boots. Plus, I know that this is a go-to combination for most women because it makes the legs seem longer. Besides, who doesn’t love long legs? It’s every girl’s dream!

Ankle length boots with jeans is a hit combination. Making minute changes can make a lot of difference and give you a new look every single time. Fold the bottom of your jeans for a tomboyish look; fray the hemline for a distressed look; fold the edges of the jeans inward – all of these are interesting ways of styling your ankle length boots. Or, zipper boots and the high rise ones are an option you always have as long as your denim are sleek. One last thing, if you do not own a pair of ankle length boots yet, you must treat yourself to a pair of black, gray or red boots – they can be quite handy.

2. How To Wear Boots With A Skirt?

Pairing Boots With A Skirts
Image: IStock

If you are a beginner, pairing boots with skirts can seem a little tricky to pull off, but it’s not all that bad. It strikes a balance between the girly and not-so-girly elements of the boots. The idea is to maintain a balance.

Instead of your usual jeans with ankle boots, go for a sleek pencil or A-line skirt that runs a little below the knees. Or, if fall is around the corner and you cannot wait to flaunt those knee-high boots, go for a shorter skirt that is just above the knees and ensure that there is enough space between the two of them (otherwise, it can look quite sloppy). Also, the end hem of the skirt cannot eat into the edge of the boots. Another option is the classic calf length boots that end above your calves and below the knee – they are classic, classy, and stylish. Sporting a skirt with boots enhances your silhouette, making your legs look sexier than they already are.

3. How To Wear Boots With Dresses?

Thigh High Boots For Short Dress
Image: IStock

In winters and fall, boots can come to your style rescue. All you need is a dress and a pair of boots to make you look stylish at the snap of a finger. Thigh-high boots invariably go with any or all short dresses. Or with a maxi dress with slits. Of course, not to forget the ankle length boots that go with all of those flouncy hemlines.

4. How To Wear Boots With Leggings/Jeggings/Tights?

Suede and Chelsea Boots With Leggings
Image: IStock

Listen up – come winter, you are practically going to live in them. Leggings, jeggings or fleece tights, and a pair of boots. Layer the outfit or go with loose shirts, long jackets or capes. Zipper, suede, and Chelsea boots can spruce up your style quotient. This is one trend that is never going out of style, so there’s nothing to worry about.

5. How To Wear Boots With Ankle Pants?

Distressed Ankle Pants With Ankle Boots
Image: IStock

Here is a simple rule of thumb – ankle length pants equals to ankle length boots. They look great with any ankle length trousers like distressed jeans, pants folded at the hemline, ankle length leggings/jeggings or leather pants. Moccasin Minnetonka boots, suede or Chelsea boots are all great options.

[ Read: How To Make Ripped/Distressed Jeans- DIY ]

6. How To Wear Boots With Shorts/Capris?

Ankle Length Boots With Shorts And Capris
Image: IStock

Shorts and boots are a quintessential combination in spring, summer or fall. Well, if it were up to me, I’d love to wear them in winter, but you know that is not so practical. Anyway, coming back to boots and shorts, these are stylish and a smart way to camouflage those big calf muscles or short legs. They create a flattering, elongated illusion. Pair shorts with sleeves, tank tops, and flannel shirts with Chelsea boots, the Minnetonkas or ankle length boots.

7. How To Wear Boots With Flared Jeans?

How To Wear Boots With Flared Jeans
Image: IStock

There’s a misconception that you cannot wear anything except ankle length boots with flared jeans, but you can, and we will see how. Even though ankle length boots or moccasin boots go perfectly with flare jeans, you can make do with the others too. You just need to remember that the jeans need to be well fitted up until your calves and then flare down at the bottom. Fold the bottom-most part of the jeans (the flared portion) to your shins and clip them up (optional). Now, pull those zipper boots up. This way, you can still wear those bootcut or flared jeans in winter without worrying about anything.

8. How To Wear Boots With Harem Pants?

Ankle Boots With Harem Pants
Image: IStock

Harem pants and boots? Yes, why not! I mean, edgy statements like these are fashionable and appealing. Pair your harem pants with a simple V-neck T-shirt, a printed boho top or a tank, and go with lace up or dessert boots or anything sturdy. It’s a lot of fun and feels great, trust me!

Pairing Boots With Seasonal Outfits

  • How To Wear Boots In Summer
Ankle Boots In Summer With Outfits
Image: IStock

It felt like a ridiculous idea when I first looked at my friends wearing boots in summer until I bought myself a pair at a sale that I could not wait to flaunt. So, I looked it up, and it’s a thing. But, just make sure that the remaining part of your outfit is breezy, soft or airy. Otherwise, it can get very uncomfortable (remember, the Ross and the leather pants episode?). Ankle length or moccasin/Minnetonka boots are your best bet.

  •  How To Wear Boots In Winter
Winter Ankle Boots with Outfits
Image: IStock

We think winters are all about the UGGs. Yes, of course, they are everything you need to ‘make winters great again’, soft-warm-stylish! But, there’s more you can do apart from UGGs and not-so-great looking snow boots. Like we discussed, knee, calf, and ankle length boots go with most of your winter outfits. If you live in a city where snow boots are a must, consider switching to other fashionable options.

  • How To Wear Boots In Monsoon
Ankle Boots In Monsoon
Image: IStock

We all complain about not having enough rains when it does not rain, and then we complain when it rains. That’s because we hate the splatter and stepping into puddles and dirtying our outfits. But come to think of it, it is not all that sloppy! You just need simple monsoon gumboots, and you are sorted.

  • How To Wear Boots In Fall
Knee Length Boots In Fall Outfits
Image: IStock

Dresses, boots, and pumpkin spice latte – that’s what fall is about. So, it’s probably safe to say that boots with any outfit are acceptable. So, go ahead and use the options we have discussed and slay it in style this fall!

Expert’s Answers for Readers Questions

How to wear boots with trousers?

Wearing boots with trousers is not very different from wearing them with jeans, leggings or jeggings. Except when you are trying to wear them with not so skinny formal pants or chinos. In that case, your best bet is the ankle length boots. When we say ankle length boots, there are a ton of options in this variant, and smart ones too. So, yes, that is what you will need.

How to wear ankle boots with rolled jeans?

Ankle length boots or moccasin/Minnetonka go best with rolled up jeans/trousers or anything that stops at the ankle. That is, if you want to show off the rolled up style.

How to wear ankle boots with straight leg jeans?

First of all, anything and everything will go well with straight cut jeans, especially knee length boots or even thigh length ones if you can carry them off.

So, now you get the hang of it, don’t you? I’ll leave you with the thought that we have inspired you enough, and you can take it from here. Go on, walk out in style!

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Pratima Ati
Pratima AtiFashion & Lifestyle Writer
Pratima Ati is a postgraduate in International Business from Staffordshire University. After working in Marketing and Business Development for a few years, she jumped ship to pursue two things she loved – fashion and writing.

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