Five Outfits With Bootcut Jeans: Casual, Work, Date Outfits

Ways to Wear Bootcut Jeans

Outfits With Bootcut Jeans

A few weeks ago I showed how to wear bootcut jeans for warmer summer-ish weather and then later for cooler weather. I know many of you find it refreshing to see outfits with bootcut jeans, so today I’m pulling together some from the archives to show a few ways to wear bootcut jeans: for casual dates, a date, and work!

Before we get there, let me point you to different bootcut jeans worth checking out. Mine are from Wit and Wisdom, and they actually have several different washes right now. I’ve tried two of the washes and they are both VERY stretchy and SO COMFY. They even have elastic in the waistband for extra comfort! 🙌🏽 They loosen up a bit after a few hours, but not enough for me to size down. I size up to 8 in these for them to be looser around my thighs and a little longer.

Wit and Wisdom bootcuts are 32” long in regular and 30” in petite. If you need a longer pair, below are some recommendations.  Both brands are known for being soft, stretchy, and comfy, too.  I haven’t tried all the exact pairs below, but I’ve tried skinny jeans from all the brands and can attest to how soft and comfy they feel.



I recommend wearing bootcut jeans with heels, like pumps, wedges, or wedge sneakers.  The proportion of the top half and bottom half are cut in a way that assumes you wear them with a heel.  You can, of course, do whatever you want!  But IF you are looking at your outfit with flats and thinking, “Why do I look like I’m swimming in these?  Why is this material bunching so much around my feet?  Why do I look shorter than usual?” try wearing them with a heel to see if that helps.

Alright, here are some outfit ideas!

SIZING: I’m 5’6″ and usually S/M or 6 in clothes, 8.5 to 9 in shoes.


striped tee + orange cardigan + bootcut jeans + wedges

Casual Outfit #1: Tee + Cardigan + Wedges or Booties
For an easy casual look, try bootcut jeans with a t-shirt and cardigan.  You’ve seen me do this with skinny jeans a thousand times, but bootcut jeans offer a nice change.  If open toe wedges feel too dressy, try wedge sneakers or heeled booties like THESE.

Shop the Outfit:
Top: Target (similar)
Sweater: Nordstrom (This year’s version–wearing size XS )
Jeans: Nordstrom (exact–wearing size 8)
Wedges: Old Navy (similar, similar)
Purse: Nordstrom (similar)
Necklace: Dear Mushka (exact)


mustard sweater + bootcut jeans + wedges bootcut jeans + mustard sweater + wedgesBootcut Jeans Yellow Sweater Tan Booties

Casual Outfit #2: Pullover Sweater + Wedges or Booties
Another outfit to try is bootcut jeans with a pullover sweater.  For a casual vibe, go for a sweater that’s relaxed.  I first showed this sweater last year and got quite a few questions about it.  It’s thin and somewhat see-through since the lines that make the diamonds are perforated.  It was sold out last year, but it’s BACK–hooray!  Comes in XXS to 4X HERE.  I’m wearing size M and it’s got a bit of room for a looser fit.

Again, if open toe wedges feel too dressy, try wedge sneakers or heeled booties like THESE.  The last pic is the same outfit with booties instead of wedges!

Shop the Outfit:
Sweater: ModCloth (exact–wearing size M)
Jeans: Nordstrom (exact–wearing size 8)
Wedges: Old Navy (similar, similar)
Purse: ModCloth (similar)
Necklace: Dear Mushka (exact)


maroon top + bootcut jeans + wedges + cognac totebootcut jeans + maroon top + wedges + cognac tote

Date or Dressy Casual Outfit #1: Nice Top or Blouse
It’s easiest to dress up bootcut jeans that are a darker wash.  To do so, pair it with a nicer top, whether one in material that’s nicer than cotton, one that has details like flutter sleeves, ruffles, or peplum, or both.  Be sure to add accessories, and you’re ready to head to lunch with friends!  One of my go-to earrings for nicer looks are these Antique Brass Gems.  They’re metallic statement earrings that are made of leather, so they are incredibly lightweight and easy to wear. 👏🏼  Find them HERE.

This top is a few years old and no longer available, but any nicer top you have works!

Shop the Outfit:
Top: ModCloth (similar, similar)
Jeans: Nordstrom (exact–wearing size 8)
Wedges: Old Navy (similar, similar)
Tote: Nordstrom (exact)
Necklace: Dear Mushka (exact)
Earrings: Nickel&Suede (exact–wearing size M)


grey sweater + bootcut jeans + leopard print heels bootcut jeans + grey sweater + leopard print heels

Date Outfit #2 or Work #1: Fitted Sweater + Leopard Print Heels or Booties
In one of the previous outfits, we talked about using a relaxed sweater for a casual look.  For a dressier look, wear a fitted sweater with a special feature like a faux wrap, puffed sleeves, pom poms, etc.–whatever floats your boat.  I topped off the outfit with leopard print pumps.  I like to add a print to elevate an outfit of all solids.  But, brown pumps would work well, too!

My pumps are from the Nordstrom Anniversary Sale back in July, and they have since sold out.  But there is a newer, nearly identical version by the same brand HERE.  Mine feel sturdy and well-made, with padding in the footbed.

This is a nicer casual look for meeting friends for lunch, or it could work for a polished Casual Friday outfit for work.  If you need a warmer shoe option, go for a cognac bootie or leopard print bootie.  Keep the outfit looking sharp with a bootie that has a skinnier heel and pointier toe like THESE.  They’re super comfy!  I wear those in size 8.5.

Shop the Outfit:
Top: Nordstrom (similar, similar, similar)
Jeans: Nordstrom (exact–wearing size 8)
Heels: Nordstrom (exact-wearing size 8.5)
Tote: (similar)
Necklace: Dear Mushka (exact)


white top + knit blazer + bootcut jeans, +leopard print heels business casual + white tunic + knit blazer + bootcut jeans + leopard print heels

Work Outfit #2: Blouse + Blazer + Heels
Lastly, pull together a work look with a blouse and blazer.  This is the white tunic that I’ve been telling you about for years.  Super versatile!  See ways I’ve worn it HERE.  It is somewhat see through in white and requires a camisole.  I wear size M.  Find it HERE.

I paired it with a knit blazer that looks tailored and is very thick, but it’s also very stretchy and comfy!  My blazer is old, but a new version is available in regular and petite HEREPlus sizes HERE.  The new version runs small, I wear M.

Shop the Outfit:
Top: Nordstrom (exact–wearing size M)
Knit Blazer: Nordstrom (exact–wearing size M)
Jeans: Nordstrom (exact–wearing size 8)
Heels: Nordstrom (similar-I wear size 8.5)
Tote: Nordstrom (exact)
Necklace: Dear Mushka (exact)


Those are a few outfits with bootcut jeans you can try this fall!




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