Ankle boots, or booties, are a great smart-casual style of footwear to add to your wardrobe.

A more practical, versatile relative of knee-high boots, pairing boots with jeans is fast becoming a fashion staple in many a shoe closet.

The two biggest challenges to overcome in successfully pulling off a look with boots, however, are the illusions of ‘fat ankles’ and ‘short legs’. This has less to do with the body type of the wearer than the natural shape of boots.

These challenges can be especially worrisome when wearing jeans or pants, but FRET NOT. Read on for our handy guide to wearing boots with jeans in a flattering, stylish manner!

Wearing Boots with Jeans – The Tips




If you’re wearing a pair of skinny jeans or jeggings that are fitted at the ankles, simply tuck them into your boots for a neat, continuous line down the length of your legs. This only works for jeans that are fitted at the ankles!

If your jeans are looser, however, the fabric would likely bunch up around the ankles and look messy.

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The most common variation of pairing boots with jeans – rolling the hems just above the ankles, to the approximate level where the rim of the booties starts. Showing a bit of skin between the rolled hems and the booties also helps to create a positive visual illusion of longer legs. Properly wearing boots with jeans is all about playing with the length of the legs.

Boots with jeans

Boots with jeans                                           Boots with jeans


Boots with jeans

A quicker, more casual alternative to rolling the hems of your jeans would be to cuff your jeans instead. Do note that shorter cuffs are highly preferable, especially if your legs are naturally not as long.

This is one of the most popular styles of pairing boots with jeans – just take a look around you!

Boots with jeans                                                                      Boots with jeans


Boots with jeans

Finally, you can go for an all-black ensemble by pairing black skinny jeans with a pair of black booties. This is your chance to have fun with textures and embellishments – studs and chains on your boots, or jeans that are ripped and frayed.

This look tends to work best with skinny jeans or very slim-cut jeans only, as they flatter the shape of your legs.

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Rock Your Booties With Jeans!

Check out fashion blogger Wendy Nguyen’s video on how she wears her ankle boots!



Did we miss out any of your favorite ways to style your boots with jeans? Let us know in the comments below!

Don’t forget to check out our website for hundreds of different styles of ankle boots, and more. And be sure to reach out to us @picvpic with your favorite tips on wearing boots with jeans!