Winter Boots with ’90s Straight Leg Jeans (A Sorel Try-On & Styling Experiment)

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Alright, let me start by saying this is mostly a post dedicated to a handful of new and truly stunning designs of Sorel boots for this year. You have to see them, the colors are beautiful.

It’s also kinda, sorta about trying on said winter boots with the one style of denim I most frequently find in my closet right now — straight leg jeans, that have more of a loose structure than a fitted one. This choice came about naturally because, well, I don’t own skinny jeans anymore (didn’t realize until prepping for this very post that I donated the last of them this summer). While I do have a pair of coated skinny pants, and a plethora of my favorite leggings, I knew this would be the ideal time to see what the future of my recently evolved stack of jeans means for my winter boots. 

Sorels & ’90s Straight-Leg Jeans: A Winter Boots Try-On Sesh

It’s also kinda, sorta about trying on Sorel winter boots with the style of denim in my closet right now -- '90s straight leg jeans, more loose than fitted.

Base outfit: Sweater (L) | Jeans (28)

Boots: left | middle | right

It isn’t lost on me that the younger generations (and professional styling images I keep coming across on retailer websites, for that matter) have a very simple solution to our latest denim trends paired with boots.

They are simply stuffing the baggy jeans right down into them. Cowboy boots, classic winter boots, UGGs. Anything goes, and it feels a bit oblivious to fashion structure, if you will. Almost lazy, or rebellious in nature. 

Which can only mean one thing….I’m officially old for thinking that. 

1. Sorel Tofino™ II Boots –
Straight-Leg Jeans Tucked In

It’s also kinda, sorta about trying on Sorel winter boots with the style of denim in my closet right now -- '90s straight leg jeans, more loose than fitted.

Backcountry | Zappos | Sorel

But even if I’m growing old, I’ll never be too cool for trying out a style. I’ll try anything, really, even if I “already did that.” I love evolving trends and the nostalgic nature of fashion inspired from the past. 

I was ready to try this one out for myself.

It’s also kinda, sorta about trying on Sorel winter boots with the style of denim in my closet right now -- '90s straight leg jeans, more loose than fitted.

Backcountry | Zappos | Sorel

While it felt a bit weird on my own body as I stuffed my straight-leg jeans into boots, I must admit that the carefree vibe of it all is extremely alluring, and very Princess Diana (one of my fashion icons who once rocked this look so well with cowboy boots herself). 

This Tofino II boot went like wild during Cyber Week sales, but if you can find your size they are gorgeous. I tried on two colors because I couldn’t resist, and now I wish I had also tried the color “curry”. I have an older version of these boots and they actually made this new one slightly smaller in size, which I love (the less clunky my shoes all winter, the better). I recommend sizing up a half.


2. Sorel Harlow™ Lace Cozy Bootie –
No Denim-Stuffing Required

It’s also kinda, sorta about trying on Sorel winter boots with the style of denim in my closet right now -- '90s straight leg jeans, more loose than fitted.
It’s also kinda, sorta about trying on Sorel winter boots with the style of denim in my closet right now -- '90s straight leg jeans, more loose than fitted.

Sorel | Backcountry | Zappos | Macy’s

Boots that don’t require stuffing, if you will.

These are meant for lighter winters, but something about me decided to take the chance on them. They are waterproof like all the others and truly cozy. It helps, of course, that these are the most like sneakers and subsequently, the easiest to wear with my jeans. I can’t help but think these would be great with cropped jeans and cozy socks peeking out, too!


3. Sorel Explorer™ II Joan Cozy –
Lightweight Boots + Better In-Person

It’s also kinda, sorta about trying on Sorel winter boots with the style of denim in my closet right now -- '90s straight leg jeans, more loose than fitted.
It’s also kinda, sorta about trying on Sorel winter boots with the style of denim in my closet right now -- '90s straight leg jeans, more loose than fitted.

Sorel | Zappos

I’m going to be honest here, I didn’t like these online. I thought they were a bit too yeti monster for me, which is saying something since I collect all things fleece and sherpa. They seemed to create a lot of excitement upon release, however, so I figured the joke would be on me if I didn’t at least try.

These are actually great. Much easier to look at in real life, and a cozy yet lightweight boot option for winter!


4. Sorel Explorer™ II Joan –
The Ones With The Best Color Updates

It’s also kinda, sorta about trying on Sorel winter boots with the style of denim in my closet right now -- '90s straight leg jeans, more loose than fitted.
It’s also kinda, sorta about trying on Sorel winter boots with the style of denim in my closet right now -- '90s straight leg jeans, more loose than fitted.

Backcountry | Sorel | Zappos

These wildly popular boots get the best color updates in my opinion; it was almost hard to choose from the lineup this year. I love how neutral these are while still being very interesting and full of style!


5. Sorel Out ‘N About™ III Puffy Lace Boots –
Just Right For Cropped Jeans

It’s also kinda, sorta about trying on Sorel winter boots with the style of denim in my closet right now -- '90s straight leg jeans, more loose than fitted.
It’s also kinda, sorta about trying on Sorel winter boots with the style of denim in my closet right now -- '90s straight leg jeans, more loose than fitted.

Sorel | Zappos

As my try-on continued, I began to realize many of the popular boot styles are mid-height…not quite tall enough for stuffing my jeans into, but not something I would want my full-length jeans to cover. I ended up doing some sort of roll with each of these mid styles, but I think they would be excellent with a cropped pair of jeans.

These moon boot-esque shoes are squishy, WARM and fun. They were almost a bit too big, but I don’t think I would size down.


6. Sorel Tivoli™ IV Boot –
For Cuffing, Not Stuffing Your Jeans

It’s also kinda, sorta about trying on Sorel winter boots with the style of denim in my closet right now -- '90s straight leg jeans, more loose than fitted.
It’s also kinda, sorta about trying on Sorel winter boots with the style of denim in my closet right now -- '90s straight leg jeans, more loose than fitted.

Backcountry | Sorel

These are a classic Sorel style that withstand the hardy winters. If you’re into seasonal colors, don’t skip the “Alpine Tundra/Dark Moss”. I size up 1/2 in these, as they are quite insulated and protected, which can make them feel a tiny bit smaller for your foot.


7. Sorel Tivoli™ IV Parc Boot –
For The Roughest Of Winters

It’s also kinda, sorta about trying on Sorel winter boots with the style of denim in my closet right now -- '90s straight leg jeans, more loose than fitted.
It’s also kinda, sorta about trying on Sorel winter boots with the style of denim in my closet right now -- '90s straight leg jeans, more loose than fitted.

Backcountry | Sorel | Zappos

If you need boots for the roughest of winters? This pair, with a whopping 200g of insulation and structure for heavy snow. They’re the boots I probably should be keeping since I live at the top of Michigan. I love their rugged nature, yet they still feel chic with this all black color (plus sherpa sticking out).

As I tried on boot after boot, the whole nonchalant look of loose jeans and boots started to grow on me. I moved past cringing and actually even ended up liking it while editing these images my husband snapped.

It’s also kinda, sorta about trying on Sorel winter boots with the style of denim in my closet right now -- '90s straight leg jeans, more loose than fitted.

Sweater (L)| Jeans (28) | Boots (the ones I’m keeping!)

What started as my annual hunt through Sorel’s winter catalog evolved into an interesting experiment that had me rolling my jeans in all sorts of odd ways, even joining the rebellion by stuffing my jeans straight down into the boots. While the look is growing on me (and I’m sure I’ll be rocking it by next week), I actually loved the shortest, most sneaker-like boots the most. Wearing these gives me just a smidge more time to get used to the whole baggy jeans + tall boot concept… or enough time to move to Hawaii. 

Xx,
Amy

Let’s be friends on Instagram! Sharing life from my sleepy little beach town, daily style, and my professional photo work – with a good dose of adorable toddler content too.

2 COMMENTS

  1. Love this, since just yesterday I was trying on boots and wondering how to wear them with straight leg jeans. The Mom Edit is big on sorels and they are super cute, but really hard for those of us with wider feet to wear. I would love to see some different brands featured.

  2. I know this has nothing to do with winter boots, but I’m struggling with straight leg jeans that look work appropriate/put together. Thankfully I live in CA, so no winter boots needed, but I can’t figure out cute shoes for work/how not to look sloppy at work. P.S. It is a casual office, jeans are ok, even light wash.

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