The Best Boots To Wear With Straight Leg Jeans (Madewell Slim Demi Boot)

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After introducing you to my newest favorite pair of non-skinny jeans, I wanted to see what style boot worked best with them for winter. The mid-top sneakers I wore in that post are adorable, but yes, I know…we don’t want cold ankles this winter! And I’m just not usually down with socks and white sneakers.

It’s boot season, so let’s get on with the boots!

The Best Boots With Straight-Leg Jeans For Winter

I tried three categories of boots here: western boots, heeled boots & lug sole boots. I tried a few in each category, but here you can see some examples. Spoiler alert…they all work with these jeans!

The Madewell Slim Demi is the perfect combo of straight-leg & cute bootcut jeans. The best boots to style 'em with? Think Frye, Mark Fisher & Sorel.

western boot | heeled boot | lug sole boot | jeans | utility jacket (similar) | sweater | fleece

These jeans are like the holy grail. No more weird issues with “do I cuff it?” or “where do I cuff the jean when the boot shaft is high?” or “what socks do I wear?” The perfect combo comes from the slightly wider leg in this Madewell Slim demi boot coupled with the perfect length (right above the ankle).

These are the perfect inseam for me (which is why I’m rejoicing, because this never happens) in the regular length (27.5″). But they also come in tall and petite sizing so you can get a close-to-perfect inseam in them, as well. Hacking them off with scissors at the right spot is always a good option — and one I use regularly. Don’t be afraid! Just cut a bit at a time and try on until you get them juuuust right.

3 Boot Styles To Wear With Straight Leg Jeans

1. Western Boots

Frye Reed Bootie

at Nordstrom (black & brown) | at Zappos | at Amazon

Stay tuned for my ode-to-Frye-boots coming up. I’ve been hunting for the perfect white-but-not-too-white boot for ages, and when I found these it dawned on me how many Frye boots I have that I always come back to. These are comfortable, but have a flattering heel. They’re just the perfect white. Since they’re nubuck suede, I sprayed them with a suede protectant right after I got them. I love them so much, especially how flattering the little notch in front is.

Sizing Info: Size up 1/2 size in these.

The Madewell Slim Demi is the perfect combo of straight-leg & cute bootcut jeans. The best boots to style 'em with? Think Frye, Mark Fisher & Sorel.
The Madewell Slim Demi is the perfect combo of straight-leg & cute bootcut jeans. The best boots to style 'em with? Think Frye, Mark Fisher & Sorel.

Frye Reed (go up 1/2 size) | jeans (27 reg) | sweater (s)

Free People New Frontier Western Bootie

at Nordstrom | at Free People | at Zappos

Ok, so I’m on a rad western boot kick (…pun intended?) because I’m also keeping these bad boys. LOVE. I’m in love. And what I’m also in love with, is how these boots work with these Madewell jeans, too. Skinny jeans and these boots would be fine, but I am loving that these glide right over the top, yet still show off the boot. Y’all, this is like years of searching for the right combo finally coming together. Sorry if I am totes geeking out on this. It’s what I live for — jeans and boots. Haha. I tried these in another color, too, but was not a fan of them in-person. I’ve include one pic below so you could see.

Sizing Info: I went up to a EU 39 here but am a solid US 8. 38 usually winds up being too small for me, even though some sites call a 38 an 8, I find it to be more of a US 7.5.

The Madewell Slim Demi is the perfect combo of straight-leg & cute bootcut jeans. The best boots to style 'em with? Think Frye, Mark Fisher & Sorel.
The Madewell Slim Demi is the perfect combo of straight-leg & cute bootcut jeans. The best boots to style 'em with? Think Frye, Mark Fisher & Sorel.

Free People New Frontier (tts) | denim jacket | utility jacket | jeans (27 reg)

The Madewell Slim Demi is the perfect combo of straight-leg & cute bootcut jeans. The best boots to style 'em with? Think Frye, Mark Fisher & Sorel.

Free People New Frontier (tts) | denim jacket | jeans (27 reg)

Dolce Vita Serna Calf-hair Boot

at Nordstrom | at Zappos

These boots are absolutely rad and gorgeous. They don’t really make sense for me here in rainy Portland, but if you have plenty of days without rain where you are and want some amazing white boots…these. Comfy and just freaking badass. Ooh, and they’re currently 41% off at Nordstrom!

Sizing info: True to size on these. I forgot to get a picture squatting so you can see the shaft height, but I like that it’s slightly taller 7″ height on these.

The Madewell Slim Demi is the perfect combo of straight-leg & cute bootcut jeans. The best boots to style 'em with? Think Frye, Mark Fisher & Sorel.
The Madewell Slim Demi is the perfect combo of straight-leg & cute bootcut jeans. The best boots to style 'em with? Think Frye, Mark Fisher & Sorel.

Dolce Vita Serna (tts) | jeans (27 reg) | gray sweater (s) | black sweater (s)

2. Heeled Boots

Marc Fisher Unno Pointed Toe Bootie

at Nordstrom

These are such great boots that the whole team loves. I tried them in the snake print and gah. So good. Em has them in ivory. They’re still well-stocked and on super sale in this snake print and in solid black. I love the notch at the heel for a super flattering feminine look!

Sizing & comfort info: True to size here and comfy for a boot with this high of a heel! (3 1/4 inches high)

The Madewell Slim Demi is the perfect combo of straight-leg & cute bootcut jeans. The best boots to style 'em with? Think Frye, Mark Fisher & Sorel.
The Madewell Slim Demi is the perfect combo of straight-leg & cute bootcut jeans. The best boots to style 'em with? Think Frye, Mark Fisher & Sorel.

Marc Fisher Unno (tts) | jeans (27 reg) | black sweater (s)

Steve Madden Mistin Pointed Toe Boot

at Nordstrom

I am apparently on an ivory shoe kick, too. These are so chic and comfy and a nice lower-heeled option to the pair above. These are a little more mod as opposed to the glam-vibe of the Marc Fishers, but still a great pointed-toe heeled boot option.

Sizing & color info: True to size here again and a really lovely boot. They come in black and tan suede, too.

The Madewell Slim Demi is the perfect combo of straight-leg & cute bootcut jeans. The best boots to style 'em with? Think Frye, Mark Fisher & Sorel.
The Madewell Slim Demi is the perfect combo of straight-leg & cute bootcut jeans. The best boots to style 'em with? Think Frye, Mark Fisher & Sorel.

Steve Madden Mistin (tts) | jeans (27 reg) | black sweater (s)

3. Lug Sole Boots

Sorel Lexie Wedge Boot

at Nordstrom | at Backcountry (use THEMOMEDIT for 15% off!) | at Amazon

These are a new-to-me color-way in some of our favorite winter wedge boots. These are lovely and if you’ve never had a Sorel wedge boot they are SO so comfy despite the height. I have an upcoming sneaker boot post including these so stayed tuned for more, but they’re a fabulous winter shoe if you like a little bit of flattering yet comfy height.

The Madewell Slim Demi is the perfect combo of straight-leg & cute bootcut jeans. The best boots to style 'em with? Think Frye, Mark Fisher & Sorel.
The Madewell Slim Demi is the perfect combo of straight-leg & cute bootcut jeans. The best boots to style 'em with? Think Frye, Mark Fisher & Sorel.

Sorel Lexie Wedge (tts) | jeans (27 reg) | jacket (s)

UGG Noe Moto Boot

at Nordstrom | at Zappos | at Bloomingdale’s | at Amazon

I finally tried these after eyeing them up for a while and they are AWESOME. If I didn’t already have a full combat boot collection, these would be mine. So comfy. This isn’t the sweater I’d typically pair with them…I’d probably swap for the ivory fleece jacket above or the gray sweater. But this is what happens when I get in a frenzy of excitement about trying on boots…what can I say? Honestly, these are the only boot here that I don’t adore with these jeans, but perhaps it’s the sweater throwing me off.

Sizing info: True to size and cushiony soft in the sole!

The Madewell Slim Demi is the perfect combo of straight-leg & cute bootcut jeans. The best boots to style 'em with? Think Frye, Mark Fisher & Sorel.
The Madewell Slim Demi is the perfect combo of straight-leg & cute bootcut jeans. The best boots to style 'em with? Think Frye, Mark Fisher & Sorel.

Ugg Noe Moto (tts) | black sweater (s) | jeans (27 reg)

UGG Hazel Waterproof Block Heel

at Nordstrom | at Amazon

These aren’t a boot style I’d typically choose, but I think they’d be a good choice if you need a lug sole, waterproof style you could still wear to work. They are a shade that would go with everything and would be cute with tights or leggings, too. They come in black and a cocoa brown, too.

Sizing & comfort info: These are really comfy and true to size…walkable even with the heel. The gusset at the ankle is also comfy!

The Madewell Slim Demi is the perfect combo of straight-leg & cute bootcut jeans. The best boots to style 'em with? Think Frye, Mark Fisher & Sorel.
The Madewell Slim Demi is the perfect combo of straight-leg & cute bootcut jeans. The best boots to style 'em with? Think Frye, Mark Fisher & Sorel.

Ugg Hazel bootie (tts) | jeans (27 reg)

Have you tried the Madewell Slim Demi boot jean yet or one that fits similarly? I’d love to hear of other options that have a similar straight-leg fit to these. That’s the next thing on my list is to see if there are more jeans out there with this rad fit or if these are the magical unicorns. I live in black jeans mostly in the winter, but they do come in a couple of blue washes, too, if that’s more your thing!

xo,

L

Check out the latest in my world over at @laurajansenstyle and join us in our everyday (2020-friendly style) adventuring around Portland, Oregon. If you want to shop my current pieces I’m loving and wearing, head over to My Closet! 

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