Now & Later: Bootcut Jeans for Summer and Fall

It’s during this time of year, that summer to fall transition, that I think bootcut jeans get the most attention from me.  You know that skinny jeans are my preferred cut (and it’s perfectly fine if they are not yours–we all have different body types and clothing preferences!)  But, when it’s KIND OF denim weather, like not disgustingly hot but a little muggy, skinny jeans still feel gross.  Bootcut jeans are here to save the day!

Bootcut jeans don’t suffocate your legs like skinny jeans do, so I totally prefer them in that “kind of” denim weather.  Especially my favorite Wit and Wisdom pair that I kept telling you about from the Nordstrom Anniversary Sale!  They are not super duper thick which makes them even better for this summer to fall transition.  Plus, they’re very stretchy and comfy!

Today I’m sharing two ways to wear bootcut jeans–one for NOW or early fall and one for LATER once the weather cools!

Now & Later Bootcut Jeans for Summer and Fall

Styling Tip: I recommend wearing bootcut jeans with a heel, whether pumps, a wedge, 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 does the bottom of the leg look so flared out?  Why do I look like I’m swimming in these?  Why do I look shorter than usual?” try wearing them with a heel to see if that helps.

NOTE: The jeans I’m wearing in today’s post were NOT part of this year’s NSale.  This year’s version is HERE with a slightly darker wash and navy stitching that’s “invisible.”  My version is several years old with a more medium wash and golden stitching, found HERE.  I honestly like both versions, but might prefer this year’s version more since the invisible stitching makes it easier to dress up.

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


white and tan striped tee + bootcut jeans + long pendant necklace + taupe heelsbootcut jeans + white and tan striped tee + long pendant necklace + taupe heels

Outfit #1: T-shirt + Wedges
In the summer or early fall when it’s still pretty warm, pair bootcut jeans with a t-shirt.  Bootcut jeans usually dress up pretty darn well, but that doesn’t mean you can’t wear them casually with a t-shirt, too!  I opted for an open toe wedge over booties because if it’s still warm, boots of any kind are not my preferred choice.

You can do this with any tee: solid black or white or olive or grey, a graphic tee, a striped tee of any color–seriously any tee!  BTW, this tee is BAAAAACK in a few sizes and on clearance for $7.59!  Check it out HERE.

Shop the Outfit:
Tee: Target (exact–wearing M; similar)
Jeans: Nordstrom (exact–wearing size 8; this year’s version)
Shoes: Old Navy (similar)
Necklace: c/o Dear Mushka (exact)
Earrings: c/o Nickel & Suede (exact)

Bag: Nordstrom (similar)


yellow sweater + bootcut jeans + taupe heels + taupe purse + long pendant necklace bootcut jeans + yellow sweater + taupe heels + taupe purse + long pendant necklaceyellow sweater + bootcut jeans + taupe purse + long pendant necklace

Outfit #2: Sweater + Wedges or Heeled Booties
When the weather cools, pair bootcut jeans with a sweater!  I took this picture nearly a year ago in 2018 and never posted it, but it’s perfect for this post!  Or, ALMOST perfect.  I think I’d swap the wedges to close toed wedge booties to make it even better for cooler weather, like in the pic below:

Bootcut Jeans Outfit for Fall with Mustard Yellow Sweater

Pic above was taken this year during the NSale with this year’s version of the bootcut jeans

Whatever shoes you choose, the point is, trade your t-shirt for a sweater, and BAM, fall outfit.

This sweater is from last year and sold out before I could even tell you about it, but it came back in stock this year!  It’s pretty lightweight and has perforated holes that make it KIND OF see through, but not really.  Hope that makes sense.  In all of today’s pics I’m wearing a nude bra with no camisole.  However, since this is somewhat thin, if you want to add more warmth to it, I’d recommend wearing a flesh colored HEATTECH from UNIQLO anyway.

I’ve gotten TONS of comments about this sweater, so get it while you can!  It’s available in sizes XXS to 4X HERE!  I wear size M and it has a looser fit.

Shop the Outfit:
Top: ModCloth (exact–wearing M)
Jeans: Nordstrom (exact–wearing size 8; this year’s version)
Wedge Sandals: Old Navy (similar)
Wedge Booties: Nordstrom (exact)

Necklace: c/o Dear Mushka (exact)
Earrings: c/o Nickel & Suede (exact)
Bag: Nordstrom (similar)

If you want to see more ways I’ve worn bootcut jeans, check them out HERE.  And BTW, if you ever want to see all the other ways I’ve shown ANY piece from a blog post, scroll to the bottom of the blog post under the “Never Miss a Post” section.  Find the labels/tags for the blog post in the tiny rectangles.  I tag items I’m wearing.  If you click one of those tags, it’ll take you to all my posts with that item.  Tons of outfit ideas for any piece you wish!




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