Q&A for How to Wear Skinny Jeans with Ankle Boots

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  • Question
    Do I need to tuck skinny jeans into ankle boots?
    Candace Hanna
    Professional Stylist
    Candace Hanna is a stylist and style expert based in Southern California. With 16 years of experience in the corporate fashion and personal styling realms, she runs Style by Candace, a personal styling agency that focuses on helping individuals find their personal expression through clothing. Her work has been featured in magazines such as Shoutout LA and VoyageLA.
    Professional Stylist
    Expert Answer
    No! Showing your ankles can be sexy. When you're wearing ankle boots and jeans, it looks best if you can see a little skin between your ankle and the bottom of the jeans, especially around your ankle bone. Wear cropped jeans or, if you need to, fold the boots down a little. If the boots are higher, wear longer skinny jeans tucked into them.
  • Question
    Should I roll my jeans with ankle boots?
    wikiHow Staff Editor
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    This answer was written by one of our trained team of researchers who validated it for accuracy and comprehensiveness.
    wikiHow Staff Editor
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    If your jeans are long, this is a good option. Roll up the cuffs once or twice so that the jeans end about 1 inch (2.5 cm) above the top of the boot. Keep the rolls narrow and tight so they look neat. If your jeans are short or are skinny enough to easily fit into the boot, you don’t need to do this (unless you just like the look of a rolled cuff).
  • Question
    Can you wear ankle boots with cuffed jeans?
    wikiHow Staff Editor
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    Definitely! This is a stylish look that works well with ankle boots and gives your ankles a more slimmed down appearance.
  • Question
    How do you wear ankle boots without skinny jeans?
    wikiHow Staff Editor
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    This answer was written by one of our trained team of researchers who validated it for accuracy and comprehensiveness.
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    Ankle boots are pretty versatile! You can wear them under boot-cut jeans or straight-leg jeans if you wish, but you might want to roll or shorten the cuffs of the jeans to show off the boot. They also work well with leggings or a skirt and thick stockings.
  • Question
    Can you tuck pants into ankle boots?
    wikiHow Staff Editor
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    Yes, you can tuck pants into ankle boots. This helps to make your jeans appear shorter while making your legs appear longer too. Avoid doing this with flared or bootcut jeans though, as these are too wide. Also, the boots should be wide enough to allow the pants to fit in easily.
  • Question
    What kind of jeans do you wear with booties?
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    Skinny jeans are great with booties and ankle boots; they provide a lengthening look for the leg and look good together. Cropped denim jeans and boyfriend jeans with cuffs are also a good look with booties. Wide-flared jeans can work too but they will often make the booties appear like shoes, which is okay if it's the look you’re after.
  • Question
    Can you wear ankle boots with a dress?
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    Yes, you can wear ankle boots with a dress. Choose boots that flatter your body shape and choose dresses that end above the knee for the best look. Helpful advice accompanied by images to guide you on looking great can be found here: How to Wear Ankle Boots .
  • Question
    What kind of shoes to wear with straight leg jeans?
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    A good range of shoes look great with straight leg jeans. Some examples of suitable shoes include: Ballet flats, booties, sock boots, ankle boots, sneakers, sandals and kitten heels. As with any fashion combinations though, always try your existing shoes on with your jeans and see how they look together; fashion rules aren't absolute and it's fun to work out what looks good from your own wardrobe.
  • Question
    What tops can I wear with skinny jeans?
    wikiHow Staff Editor
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    Tops to wear with skinny jeans include: Voluminous or loose t-shirts/tops; suit jackets; sweaters; long coats; button-down shirts, etc. As with any fashion advice, it's also important for you to try the tops you have in your wardrobe with your skinny jeans and see for yourself in the mirror what looks good.
  • Question
    How do you know when jeans are too tight?
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    If the jeans are digging into your skin and leaving marks of the seams on your body, this is one sign that your jeans are too tight. Another good indication is that you feel uncomfortable in them and have difficulty breathing, eating and moving when wearing them. And if the jeans create bulges of your body fat that spills out the jeans, this is another sign they're too tight. Try the next size up and judge the comfort and look against the tighter pair.
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