How to Wear Demi-Boot Crop Jeans

I’ve been all about the skinny jeans for over a decade now, but recently I’ve been intrigued by the demi-boot crop style of pants.  These pants have a boot-cut (a look I looooved back in my high school and college days) but they’re cropped and seem to have a more streamlined look to them.  They’re slim fitting through the leg until mid-calf, and then they flair out a bit…yet they’re cropped!  Pants that hit right around the ankle are my favorite (except for in the freezing cold) so I decided to buy this pair of demi-boot crop jeans from J.Crew and I’m officially in love!  They have a 9 inch rise which is great for a post-babies tummy, and they’re really comfy and I think they’re a fun current take on denim.  They run true to size, as do most J.Crew jeans and shorts I’ve tried the past few years.  This exact pair is a little limited in sizing, so here is a darling darker wash button front option and here is a traditional blue jeans color zip front pair that also looks really cute.  Below I styled them 5 different ways if you’ve been interested in the style but haven’t quite figured out how to wear them yet.  I also put together an IGTV video on Instagram, so please check that out too if you want to see how I built each outfit!

How to Style Demi-Boot Crop Denim

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how to wear demi boot crop denim with striped shirt and tory burch cardigan

Outfit #1. demi-boot crop jeans (similar here and here) | woven mules (similar here) | striped boatneck shirt | Tory Burch cardigan (I’ve owned mine since 2011 and still LOVE it.  Absolutely worth the investment.) | navy hair scarf is old from H&M

You can’t go wrong with a striped t-shirt and jeans.  Boatneck tops are my favorite long sleeve silhouette and this one is such a great one.  I threw on my 9 years old Tory Burch cardigan as an extra layer, added a sheer navy scarf to my ponytail and threw on my favorite woven mules for an easy end of summer look.

demi boot crops with linen shirt camel sweater blazer and leopard loafers

Outfit #2: demi-boot crop jeans (similar here and here) | leopard smoking slippers (mine are from 2013 but these and these are similar!  A quality pair will last you years and years and they’ll be a true staple in your closet.) | white button front shirt (mine is linen and is sold out but this one is a similar non-linen version) | camel sweater blazer 

A button down shirt is one of my favorite things to wear.  I layered a camel colored sweater blazer over it (a must-have for any closet, camel is so versatile and it’s perfect in winter and fall) and added leopard calf-hair smoking slippers.  A good pair of these are an investment but they will last you forever and they will never go out of style.  I bought mine from J.Crew in 2013!  I’ve worn out the soles after years of use but plan on getting them resoled by a cobbler one day rather than buying a new pair.  Although if I were to buy a new pair I may look into this Rothy’s pair because I’ve heard they’re incredibly comfortable and machine-washable!

how to wear demi boot crop denim with camel shirt sweater blazer and smoking loafers

Outfit #3: demi-boot crop jeans (similar here and here) | camel boatneck shirt (mine is from 2013 and it’s still one of my favorites.  No longer available but here and here are similar camel colored options) | long cream colored sweater blazer (similar) | tan smoking slippers (mine are from 2013 but these and these and these are similar)

A camel colored top is a staple in my fall wardrobe.  I bought this one in 2013 when I lived in Arlington previously and it’s still one of my very favorite tops.  Camel acts as a neutral and it’s one of my favorite ways to add some warm earthy tones to an outfit.  Throw on a cream sweater blazer when the temperature drops and some neutral loafers or smoking slippers to complete the look.  I have my eye on these camel Rothy’s if you’re on the hunt for a comfy pair of loafers!

how to wear demi boot crop jeans with madison mathews catherine top woven mules and woven headband

Outfit #4: demi-boot crop jeans (similar here and here) | woven mules (similar here) | Madison-Mathews Catherine top (runs large, size down one size) | woven headband (comes as a 3 pack for $12.99)

This is more of a summery outfit but you could throw a sweater over top to make it work on a cooler day.  Madison-Mathews makes some of my favorite embroidered and block-print clothing, and the Catherine top is so sweet that I own in in 4 different color-ways.  It works with jeans, white jeans and shorts and it’s such a classic look!  I just do a little French tuck in front to help define my waist and I added my woven mules and headband to complete the look.

demi boot crops with sweatshirt and white sneakers

Outfit #5: demi-boot crop jeans (similar here and here) | white sneakers (mine are mesh Tretorns that are no longer available.  Here are the normal canvas Tretorn sneakers, and I also have Superga Cotu sneakers and LOVE them) | no-show socks (they come as a 3 pack on Prime for $9.95 and do not slip down!) | sweatshirt (old from J.Crew but this one from Walmart is only $11.44 and looks similar and I’ve heard it’s super comfy)

This is a nice and casual way to wear these jeans.  Perfect for a day at the park or school drop off (if your kids are back in school).  A good pair of white sneakers that works well with jeans, shorts and dresses is so versatile, and Tretorns or Supergas are my go-to.  Not trendy or flashy, just nice and classic.  My sweatshirt was from the springtime and the bold color is really fun.  A follower told me about this Walmart sweatshirt though, and it comes in lots of colors and would get you a similar look for under $12!  She said that she got her normal size to wear with jeans and sized up to wear with leggings.

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Katie Vail
Katie Vail

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