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Winter Denim Lookbook – All My Favorite Jeans

November 24, 2020

I started writing my annual Winter Wardrobe Essentials post and before long I realized that my section on winter denim was growing into a post of its own. So I pivoted and decided to share with you all of my favorite jeans for winter. I’ll still be bringing you the all important Winter Wardrobe Essentials post next week, but instead of sharing all of these jeans in that post I’ll be able to refer readers back here for specific selections. That will keep that already lengthy post from becoming a monstrosity. Ha! But for now, let’s enjoy my denim lookbook.

Winter Denim Lookbook

I have grown to love high quality denim, but I don’t think that means you need to dole out hundreds of dollars for every pair. However, I do think, as much as most of us wear our jeans, it is important to have at least a couple of pairs of denim that fit and flatter you beautifully.

What I Wore on Our Weekend Outing
See the original post here. Everlane black super-straight jeans (size up) // vintage cotton New York t-shirt (wearing a small) // black and blue plaid flannel shirt (wearing a size 8) // diamond quilted vest (wearing a medium) // wedge sneakers // black crew socks // customized Elisa multi strand necklace // classic gold hoop earrings // multi strand beaded bracelet

Since most of us probably wear jeans more frequently in the fall and winter, too, I think it’s a good idea to have several pair that you absolutely feel comfortable in and enjoy wearing. For the most versatile wardrobe, you’ll probably want jeans in a variety of washes as well.

Styling a Column of Denim
See the original post. Shop the look here.

I prefer dark wash jeans for elongating, slimming and keeping an outfit more elevated. But I love black jeans for how versatile they are in my black-heavy wardrobe. Light wash jeans are perfect for pairing with sweatshirts or more casual sweaters. And medium wash jeans are probably the most versatile of all for reasons I discussed in this post, How to Work with Contrast. Then again, light wash jeans can simply provide some interesting juxtaposition for a more elegant top, as in the look below.

Rag & Bone Cate skinny jeans

For the rest of my denim lookbook I’ll be sharing specific jeans that I’m enjoying in my closet.

Style Formula #1 - Top This!
See the original post. silk top (check size chart; I wear a large) // jeans  (wearing size 30) // shoes // handbag // necklace // earrings // similar bracelets

Above I’m wearing the Rag & Bone Cate skinny jeans in a size 30. I just realized I haven’t worn these jeans in a while, and I’ve pulled them out to wear later today. I think they’re especially going to look nice with knee high boots and lighter color sweaters. These jeans are currently 25% off. Rag & Bone is a premium denim brand, but I’ve found them to be worth a good sale price. The denim is very soft and has that lived in feel and look.

J.Crew 9″ vintage straight jeans

J.Crew Straight Jeans
cotton sweater (wearing a small) // jeans (wearing 29) // belt (wearing medium) // boots (sized up .5) // necklace // earrings // bracelet (sold out – comparable substitute) // safari jacket // hobo bag (faux leather option)

This year skinny jeans and boot cut jeans are still fashionable, but straight leg jeans have taken the lead. I like the J.Crew 9″ vintage straight jeans in vintage medium wash above. They’re a great basic straight leg jean with a pleasantly relaxed fit that isn’t ultra baggy.

Levi’s 721 High Rise Skinny jean

Soft and Subtle
cashmere sweater // Levi’s 721 High Rise Skinny Jeans // 40-Hour Flats in taupe // pearl necklace old (similar) // pearl earrings old (similar) // Day Market Tote

During the winter, however, I find myself wearing my skinny jeans the most, since I wear them under knee high boots. And honestly, straight leg jeans can be a little trickier to pair with the right shoes or boots. Above I’m wearing the Levi’s 721 High Rise Skinny jean, and it’s available in a number of other washes.

AG Farrah skinny jeans

While most of my jeans are in what I consider a mid price point, I do have a few pair of premium denim jeans. By far my favorites are my AG Farrah skinny jeans. These jeans check all the boxes. They feel like real denim, but they also feel extremely comfortable. They stretch, but they don’t stretch out with wear. The pocket placement is perfection and somehow (maybe it’s the wash and the pocket placement) they just slenderize more than any other jeans I own.


Above I’ve rolled up my AG Farrah skinny jeans a couple of times, but they really feature a split, raw hem. My exact jeans are no longer available, but these are the same cut and should fit and feel similar. In the jeans above I’m wearing a 29, but I also own a pair that are just a little different in size 30. Follow the sizing information you find for a particular pair of jeans. You’ll find a full selection of AG jeans here to consider. Again, they are my favorite premium denim brand, and several styles are currently marked down.

Talbots’ denim jeggings

But I’m also a big fan of Talbots’ denim jeggings. Don’t let the name fool you; they feel and fit like jeans, not leggings.

Color Me Beautiful!
Talbots’ denim jeggings // relaxed balloon sleeve sweater // suede buckle mules

Ann Taylor sculpting pocket high rise skinny jeans

I also highly recommend the Ann Taylor sculpting pocket high rise skinny jeans. These jeans feature an elevated dark wash, so they look a little dressier. I probably actually wear these jeans the most, especially when I’m going out and want to look a little more dressed up. I’m wearing them in the photo below, taken last January. But I also wore them to church just yesterday. These high rise skinny jeans are still available and you’ll get 50% off the full price with code BLACKFRIDAY. They come in regular and curvy fit as well as petite sizes.

Warm Casual Friday Work Look
Ann Taylor sculpting pocket high rise skinny jeans // See the original post (most items sold out)

wash black super-straight jean from Everlane

I also find myself wearing my black jeans more and more frequently during the winter. Below I’m wearing my current favorites, the wash black super-straight jean from Everlane (the blue denim selection did not fit me the same at all).

Black Straight Jeans
cotton boat neck sweater // washed black super straight jeans // reversible plaid ruana // loafers // reversible belt // gold teardrop earrings //  multi strand bracelet

black Talbots ankle jeans

But for a slimmer silhouette, I also love my black Talbots ankle jeans. Remember, however, I actually cut this jeans off to make them more ankle length for me. These jeans also come in curvy fit and both sizes are currently 40% off.

Sweater Weather Outfit
cropped cable-knit sweater (50% off now for Black Friday) // black ankle jeans (I created the raw hem) in curvy fit // Toe Cap Slingback Block Heels (50% off) // classic hoop earrings  // houndstooth wool blend coat (40% off)

White House Black Market Flare Leg jeans

Of course, you also may be one of my readers who prefer flare leg or boot cut jeans. I love the flare leg and boot cut jeans at White House Black Market. They’re long enough for my 5’8″ frame, but come in several different lengths and size ranges.

Flare Leg Jeans & Turtleneck Sweater
See the original post. turtleneck sweater // high-rise every day flare jeans // boots no longer in leopard (leather Franco Sarto booties) // multi strand necklace // similar handbag // earrings // similar scarf // sunglasses

I also purchased the black bootcut high rise jeans, but I’m going to have to have them hemmed before I can wear them. Yes, they’re that long. But they’re also extremely comfortable, elongating and slimming.

I hope you’ve enjoyed my Winter Denim Lookbook. Obviously there are other jean silhouettes and options. In fact, I’ve shared these looser fit and these wide leg jeans in my videos, too. But for the sake of brevity I’m going to stop here. And really, the jeans I’ve shared above are my favorite ones to wear.

Shop for jeans

I’ve prepared shopping widgets for each category of wardrobe essentials. The links in the widgets and in the copy of this blog post are all affiliate links. If you shop through them I potentially earn a commission, but at no cost to you. Thank you for shopping through my links and helping me to be compensated for the work I’ve done to help you prepare your wardrobe for the winter.

Denim Purchasing Tip – Choose jeans that are trending but also functional for your lifestyle. Especially consider the shoes you’ll gravitate toward and buy your denim accordingly.

Let’s wrap up this denim lookbook with additional resources for purchasing and styling denim. If you haven’t already seen them, you may also enjoy the following videos from my playlists:

Fall & Winter Denim Guide for Women Over 50:

In this video I shared tips for shopping for the denim that will fit you best and work in your wardrobe. This denim lookbook highlights different denim silhouettes and trends.

7 Ways to Wear Jeans this Winter:

In this video I shared 7 different outfit formulas to wear with your favorite denim. This denim lookbook is full of outfit ideas for winter.

Don’t Miss a Post:

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Blessed for My Day

We know that God does not cause or initiate evil. He is good, so He cannot create evil. But He does indeed allow the fingers of evil to reach into our lives at time. We experience the harsh realities of a broken world such as sickness and pain and violence. Sometimes we experience the evil of other people, whether we are physically attacked or emotionally wounded. And eventually we experience the harshest evil of all when someone we love is taken from us in life’s final blow, death.

No, God does not initiate this evil, but He does allow it. And it can be equally difficult to try to grasp how a good God can tolerate such pain and sorrow. But we must do our best to keep the big picture in mind. We must pray for wisdom and ask God to help us see the world from His perspective. He does not will anyone to perish. And He sometimes uses the pain we experience to draw others to Him in an act of grace and compassion. Above all we must trust that He is indeed good and that He loves us no matter what the circumstances may look like to us.

So the sisters sent word to Him, saying, “Lord, behold, he whom You love is sick.” But when Jesus heard this, He said, “This sickness is not meant for death, but is for the glory of God, so that the Son of God may be glorified by it.” (Now Jesus loved Martha and her sister, and Lazarus.) So when He heard that he was sick, He then stayed two days longer in the place where He was. ~ John 11:3-6

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xoxo, Kay
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10 thoughts on “Winter Denim Lookbook – All My Favorite Jeans

  1. Kay, I love the J Crew vintage jeans too. Skinny jeans haven’t been working well on me these days. If I find a jean I like I usually buy two pairs. I have one a little shorter to hit wear I like jeans to hit with boots and one a little longer to go over the boots. I also have a higher and narrower shaft boot which helps with tricky lengths. When I’m out and about I’ve been wearing my Madewell Sidewalk sneakers even to work. Dessert boots are something I’ve been thinking of adding to my wardrobe.

    1. Great! Thanks so much for sharing Robyn. It sounds like you’re a woman with a plan and you’re working the plan. I love that. Yes, having some narrow shaft booties has really helped with the new straight leg jeans.

  2. Great Jean post Kay… I have said I need to find a pair of black jeans!

    I do prefer the high rise myself…..but love all the looks you’ve created.


  3. Hello Kay,

    I love your fashion posts, especially the jeans. I’m 4ft. 11in. and it is very difficult to find jeans with the right fit and length. I look forward to your daily posts.

    I pray you and your family have a Happy and Blessed Thanksgiving.

  4. Another great BFMD! I have way too many pairs of jeans in my closet. I have donated some, but I need to cull them down again. I like that you shared jeans with different price points for us. And, of course, you look so nice in all of yours. It’s looking like we will have on and off rain in south central Georgia on Thanksgiving, and the rain will settle in through the weekend, so we may not get much deer hunting in. I wish you a beautiful day!

  5. Good Snowy Morning from Colorado, Kay!

    This is a great article on jeans types and styles! I also have several pair and don’t ‘need’ jeans right now. I do prefer the straight-leg jeans and not a flare leg pant. I purchased many pair over the years from Catherine’s Plus size clothing. They now have closed because of the Covid-19 issues, as have many good companies have closed. So I will look elsewhere. Being a plus-sized lady has its challenges to locate nice clothing anyway.

    I love the styles you have completed the jeans with blazers. That is certainly a very professional look to go out for lunch or shopping (when we can go shopping again).

    I love jewelry also and make a point to always wear earrings daily. Even to meet a delivery man at my front door! LOL! And I still wear a watch daily. Even though the house has clocks and my phone has a clock. I am a retired accountant since 2006. I am now age 71.

    I may try a pair of lighter jeans. Your Lookbook has now intrigued me with how you have pulled it together. I wear a dark wash or a black jean on some days, dressier trousers on many days or a skirt and blazer.

    I really am enjoying your website and articles. And your You Tube info.

    Back to the kitchen now to bake brownies for this week for 2 elderly neighbors up the street

    Regards, A Colorado Viewer, Mrs Pat Schneider

  6. Hi Kay
    Love your posts but I don’t wear jeans everyday. Maybe twice a week, but I do wear colored jeans more because they look dressier. I wear black casual pants, leggings or black jeans more than regular denim jeans. I still like to dress up
    even if I am going to the grocery store as I have a extensive closet from working in the office before I retired and I still
    gravitate towards dressier with a lot of blazers or sweaters. I was wondering if after the holidays, and I hope the world is more back to normal and people are healthy and back in the work force, if you could show more dressy casual outfits? I love jeans but I just don’t wear them everyday.
    Thanks so much, Sherry

  7. Thank you for this post! Jeans are my favorite thing to wear. Now I think I want some jeggings. I have four pairs of colored jeans in my closet. Are they in a separate category?

    1. I kinda think of colored jeans differently, sort of like cords. Because you do tend to wear them a little differently. Also, while I do still see colored jeans in the stores I don’t see as much as I used to. So definitely wear them, but I don’t think they’re quite as on trend as they were just a few years ago.