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How to wear ankle boots with jeans

There are many different ways to wear ankle boots with jeans. Here are a few style guide ideas for how to vary this fashion pairing.

Jeans as we know them today originated in the late 19th century, with the twill cotton textile becoming a de facto fashion favorite throughout the ages. Whether as a symbol of counterculture or meeting the demands of high fashion luxury labels, jeans have the adaptability and expressivity of a multitude of styles - much like the essential form of boot style which has been adapted to fit the function and fashion of the wearer and culture throughout the ages. What better then, than to pair these two quintessential fashion items in a myriad of outfit ideas from utilitarian to fashion-forward!

Try combos of different types of ankle boots with pairs of jeans to find your favorite way of syncing these two staples. There are many different ways to wear ankle boots with jeans. 

Here are a few style guide ideas for how to vary this fashion pairing:

  • Wear skinny jeans with hems rolled slightly above ankle boots with a pointed toe for a sleek, modern silhouette. Wearing ankle boots with skinny jeans is a great go-to outfit, and looks great with blue jeans or black skinny jeans or even white jeans - all can be paired with a simple or graphic t-shirt and black booties to look casual and pulled together.
  • Cropped skinny jeans paired with ankle boots are a casual and effortless appearance. This is a great way to lengthen your leg while showing off your ankles. Check that cropped jeans hit right at the ankle bone so that they don't bunch up or flare out. You can also try pairing this look with a pair of ankle socks or tights for a more polished look.
  • Cuffing your jeans with a fold or two is an alternative put-together look. Straight leg jeans that are rolled up and paired with combat boots give a rugged, casual vibe, and when paired with a blazer or cardigan, exude an edgy air. Blundstone Women's #2219 Chelsea Boot or Blundstone Men's #1930 Chelsea Boot in rustic brown leather are great for this look. Opt for a cropped straight jean, paired with a chisel toe western-style boot for a cool, modern Western-inspired outfit. Tucking your straight jeans into a block-heel ankle boot creates a polished ensemble that is sophisticated and minimalistic, as Chelsea boots paired with your straight jeans are always timeless.
  • Selecting a more pointed toe ankle boot with a slight heel will elongate your legs when wearing bootcut jeans outfit.


  • Pairing your bootcut jeans with Blundstone Women's #1677 Heeled Boot or Blundstone Men's #1308 Dress Boot in rustic black or brown leather to give off a slightly bohemian and Western-inspired outfit. Opt for a cropped bootcut style of jeans, worn with ankle boots for a contemporary and chic appearance. Choose a pair of boots with a pointed toe or a heel to elongate your legs. High-heeled ankle boots with slight detailing can add a touch of glam to your bootcut jeans.
  • For flare jeans, whether a subtle or more wide-leg jean, like bell-bottoms, opt for ankle booties with a slightly lower ankle length, as the wider pant leg will fall over the top of the boot without catching - making this a go-to, perfect ankle boot outfit. Blundstone Women's #1970 Ankle Boot or Blundstone Men's #1306 Ankle Boot in rustic brown leather are best suited for this style.
  • For relaxed boyfriend jeans, roll up the hem of your jeans and wear them with Blundstone Women's #1448 High Top Boot or Blundstone Men's #1935 Lace-Up Boot in black or brown leather for an effortlessly casual look. Achieve a relaxed style with chunky lug sole boots and a grunge-inspired outfit. If you are after a cozy, comfy look, pair boyfriend jeans with oversized boots for a relaxed and cozy appearance. Try a contrasting color, patterned boot, or faux leather to add a pop of visual interest to your relaxed jeans. To achieve an over the boot look that is edgy, ensure that the jeans are a looser fit so that they don't feel too tight or restrictive and pair the outfit with a full length jacket to balance out the proportions.
  • Experimenting with different heights and styles of ankle boots, like full length and knee-high, creates a contrast with your relaxed jeans. Roll up the leg of your jeans, either once or twice, to create a clean cuff, before them tucking them into the top of boots for a relaxed fall outfit.
  • Mom jeans that have a relaxed, high waisted look and feel, can also be paired with minimal ankle boots that have that trendy look, slipping over the top of the boot with just a peek of your footwear.
  • What about denim dresses? Blundstone Women's #585 Chelsea Boot. Try teaming a denim dress with this flat ankle boot for a relaxed dressed down look with off-duty style. Ankle boots can add a different touch to a stylish feminine outfit. Ankle boots can give a hint of refinement to an otherwise dressed-down look. Dress this look up, for an on trend look with a sophisticated heeled ankle boot.

Ankle and Chelsea, Which to Boot and Why?

Ankle boots and Chelsea boots are both stylish, versatile footwear that can be worn with jeans. Some key differences between the two styles however, may make one a better choice for you than the other.

Ankle boots typically have a shorter shaft that falls just below the ankle, while Chelsea boots have a slightly taller shaft that extends to the low-calf. This difference in height can make ankle boots a great match to be worn with a wider variety of pants and skirts. Chelsea boots make a better choice for colder weather, and are easy to slide on and off. 

Ankle boots typically made from suede or canvas have a more casual look than Chelsea boots, often made from more formal materials, such as leather or suede, with a sleeker, more streamlined look. Whether with shorts or leisure wear like joggers or leggings, comfortable ankle boots are a style for all seasons.

Ultimately, the best choice for you will depend on your individual style and needs. If you are looking for a versatile boot that can be worn with a variety of outfits, then ankle boots may be a better option for you. If you are looking for a boot that is more stylish and can be dressed up or down, then Chelsea boots may be preferable.

No matter how you choose to wear them, ankle boots are a stylish and versatile way to add some edge to your everyday wardrobe.

Here are some additional style tips to consider if you’re wearing ankle boots to suit your personal style: 

  • Choose the right height and style of boot for your body type. Petite types do well with a shorter shaft and pointed toe to elongate the legs. Taller figures look great in a pair of ankle boots with a taller shaft or a wider heel.
  • Ensure a proper snug fit for your boots - not too tight or too loose.
  • Wear socks or tights with your ankle boots that provide warmth and comfort.
  • Take care of your ankle boots by cleaning them regularly and conditioning the leather to keep them looking their best.

View our full range of Blundstone Boots for men and women via the links below.