How to Wear Jeans with Ankle Boots

Retirement Mode has fully set in and with that my daily wardrobe has changed slightly. Jeans and boots have become a staple. But have you ever looked in the mirror and wondered how to wear your jeans with ankle boots? I have, I want to look cool and stylish or at least put together so the silhouette matters.

Wearing jeans with ankle boots can look so wrong or so right depending on how you style them. Now that may sound hardsh but there truly is a best or better look when pairing the two items together.

Lucky Denim / cream Sweater / Poppy and Peonies Bag / Nora Cora Boot

How to wear Ankle Boots with Jeans

First of all there is a ” Depends” and I don’t mean the wet proof protection. It actually depends on the type of Boot and the style of jeans.

I know I said ankle boots so what the heck do I mean by type right? Well, ankle boots typically come in three main styles: Short which end right at your ankle, the medium which is just above the ankle and “Tall” or one that comes midway between calf and ankle. And lets not even mention the various heel heights. or maybe I will. Ankle boots have various heel styles and heights; is it flat, chunky, kitten, skinny, high, lug, darn the list is long.

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Shein Rainbow sweater / jeans/ Shoe Dazzle Lug Boot

Denim Styles We Wear

Denim aka Jeans come in so many different styles, Skinny, Straight, boyfriend, flare, wide Trouser again an infinite list of possibilities. For today I am going to focus on the styles I recommend with an ankle boot.

Normally, my focus on Ankle Boots would be pairing them with Straight, Skinny or Boyfriend. Note that a Trouser and Wide also work.

The normal “rule” when pairing the jeans with an ankle boots;

• Skinny- go cropped, flat or chunk heel or lug sole
• Straight Leg- flat chunky lug and even a higher heel
• Boyfriend same as above
• Wide leg denims- can be done but add some height in the heel, unless you are tall
• Trouser- medium or high ankle boot but again add a heel

Ankle Slouch Boot/ Old Navy Boyfriend Denim / Poncho

My Jean Styling with Ankle Boots

True confession over the past probably 10 years I have focused exclusively on skinny and distressed boyfriend denim. I was stuck in a style rut. This year I have finally branched out to a trouser jean and a straight leg, and I am loving them. Slightly more difficult on the footwear, only because I am still finding my style direction.

and FYI Skinnies work under a dress too.

White skinny denim / Rodeo Cowboy boot / Old Navy Tunic/ Brown Moto

Lets Style a Skinny Jean with an Ankle Boot

Skinny Jeans have been my standard and usually I test out either ticking them in if i have a looser boot or tey a rolled up crop style. As an FYI a boyfriend and skinny jean also are great with the cropped or rolled up cuff and an ankle boots.

• Skinny jeans should be tucked into an ankle boot with a higher shaft
• Create a cuff or a crop with the short or medium ankle
• Any of the heel heights will work with a skinny

Haggar Denim / Shein Blazer / Leopard Boot

Ankle Boots with a Straight Denim

A straight jean is very similar to a skinny, basically the leg is slight looser on you but it is consistent from thigh to ankle, does that make sense? I most often wear my straight cuffed with a low or medium ankle boot. When paired with a higher shaft I recommend the denim be worn over the shaft for a cleaner line.

• Straight jeans are worn over an ankle boot with a higher shaft
• Create a cuff or a crop with the short or medium ankle
• Any of the heel heights will work with a straight

Northern Reflections Sweater and vest / jeans / White Chelsea Boot

Boyfriend Denim and Ankle Boots

My next all time fav or on constant repeat jean has been a distressed Boyfriend from Old Navy. This is a cropped denim which works perfectly in all seasons depending on the footwear. Here I styled them with a higher shaft ankle boot and had the cuff just cover the top of the boot. I also have worn them with a low and medium. Distressed Boyfriend jeans work with all styles of ankle boots.

• boyfriend jeans should be worn over an ankle boot with a higher shaft and never tucked in.
• Create a cuff or a crop with the short or medium ankle
• wear full length with all of the ankle boots
• Any of the heel heights will work with a straight

Ricki’s Stripe Sweater / Trouser Denims/ Shoe Dazzle Boots/ Moto Jacket

Trouser Leg or Wide Leg Denim with Ankle Boots

Trouser leg and Wide legs are back in style. I wasn’t actually sure about this one until I put a pair on. My goodness, universally flattering on most body types. Trouser jeans felt like a dream and are easily dressed up or down.

This is the easiest style to match with an ankle boot, any type and heel work and you basically go as is. No cuffs, no tucks, no rolls just them as they are.

• trouser or wide leg jeans are worn over an ankle boot
• Any of the heel heights will work
• a cropped version could work well with a more fitted high shaft ankle boot

H&M (Sweater Similar) / H&M Jeans / Shoe Dazzle Boot

What about a Flare Denim

Flare Jeans like the wide leg and/or trouser jeans can go with any ankle boots. But I recommend worn covering the full shaft. A cropped version would work if you have a bit of height. You will notice I have a tendency lately to stick to a flat heel, a lug sole or a chelsea boot. Obviously, my loafers will be covered in a whole new post.

• Flare jeans are worn over an ankle boot
• Any of the heel heights will work
• a cropped style could work but with a much smaller flare.

Any popular style I may have missed? I am curious, are you wearing ankle boots with your denims? Let me know in the coments below.

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