6 Fall and Winter Denim Outfits that Are Both Cool and Classy

Can you imagine your life without jeans? I can't. Especially blue jeans. The versatility they deliver is unmatched and I am keen on seizing every opportunity to make the most of them. Jeans offer a myriad of options that guarantees something for everyone. Whether it's the cut, the wash, the closure style, the rise, the material, you're sure to find yourself a denim staple you'll be able to pair with just about anything. I shared how I styled my favorite blue jeans in this post but I also love to indulge in a good distressed pair for maximum cool factor. And the beauty of the cool seasons is that layering makes for endless possibilities to style a pair of jeans. You can go for a cropped jacket, puffer vest, the quintessential trench coat, a leather jacket, and the list goes on. Read on for a dose of inspiration on how to style your favorite jeans this Fall and Winter.

1. Blue Jeans With a Striped Tee and Blazer

I've said it before and I'll say it again: jeans and a blazer are perfect for days when you just can't decide what to wear but still want to look put together. I styled these blue straight-leg jeans from Gap with a striped tee I scored at Target and the perfect black blazer from Express. This look was super easy to assemble and definitely checks the smart casual box. While the colors are easy on the eye, the top also delivers the distinctive black and white contrast we all love. This outfit is a true multi-tasker that is appropriate for both the office and off-hour feats. I opted for strappy sandals but you could easily swap those for black pumps or ankle boots and still look absolutely posh.

Shop the look here.

Fashion and style blogger Farotelle wearing an outfit that consists of high-waisted blue jeans, a striped tee and a black blazer. She is also wearing black strappy sandals and holding a black handbag. She has dark skin, short hair and is in a standing position.

2. Blue Jeans With a Cropped Jacket

It's good our clothes can't speak because if they could, this Ann Taylor plaid tweed jacket would have asked for a break! It's one of those pieces in my closet that I reach for often because it's so good. It pairs well with skirts, dresses, dress pants and jeans alike. Here I wore it with two other favorites in my wardrobe: a black turtleneck sweater and those Gap wide-leg blue jeans. This is a look that takes absolutely no effort and yet packs so much polished punch. The jeans' straightforward cut and classic blue hue make them perfect for work and play. The turtleneck sweater adds instant polish to the look and the cropped jacket elevates it to business casual level. For a more casual vibe, I removed the jacket and was left with the simple chic of blue jeans and fitted turtleneck combo. This is definitely a look anyone can pull off.

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A woman wearing blue jeans with a black turtleneck and plaid cropped blazer. She is wearing black heels and is leaning against a brick wall.

A woman wearing blue jeans with a black turtleneck and plaid cropped blazer. She is wearing black heels.

A woman wearing blue jeans with a black turtleneck. She is holding a plaid jacket and wearing black heels. She is leaning against a brick wall.

3. Blue Denim Skirt With a Faux Leather Blazer

ICYMI, I talked about the versatility of faux leather in this post. Faux leather has been having a moment on the fashion scene and I have fully embraced it. I especially love faux leather blazers because they really have that dressy yet cool factor. For this street style-inspired look, I went for a black faux leather blazer on top of a faux leather shell top and a front slit blue denim skirt. Denim skirts have also been in vogue and styling this one with the faux leather blazer was like an outfit match made in heaven: it worked beautifully. I finished the look with black leather knee-high boots to play up the rockstar vibe.

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A woman wearing a blue denim skirt with a black faux leather blazer. She is also wearing black knee-high boots.

A woman wearing a blue denim skirt with a black faux leather blazer. She is holding a blue handbag with a chain strap.

A woman wearing a blue denim skirt with a black faux leather blazer. She is also wearing black knee-high boots and holding a blue handbag.

4. Blue Cropped Wide Leg Jeans With A Shirt and Cami

When it's layering season, you layer, it's that simple! I went for a triple layer in this look to give it distinctive interest. It all started with these Levi's cropped wide-leg blue jeans. I scored those at Nordstrom Rack a few years ago and let me tell you, they are one comfy piece of garment, a pair of jeans I can wear without having to do the wiggle-and-pull if you know what I mean! After the blue jeans, I went for a classic white button-down shirt. Everyone needs at least one of those! I have well over a handful of them but that's besides the point! I could have stopped at the blue jeans and white shirt because those two make for a full-fledged outfit but I wanted more pizzazz so I added a fitted laced up cami for a layered effect and finally threw on a plaid coat for the cozy factor. This look blends business casual and street style in a way that is suitable for a variety of settings.

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A woman wearing cropped blue jeans with a black corset top over a white shirt. She has on black boots and is holding a black handbag. She is wearing chunky gold earrings and sunglasses.

A woman wearing cropped blue jeans with a black corset top over a white shirt. She has on black boots and is holding a black handbag and a plaid coat. She is wearing chunky gold earrings and sunglasses.

5. Distressed Blue Jeans with A Trench Coat

Who doesn't love a trench coat? Trench coats add a refined and modern touch to any look. And if you're like me and enjoy the contrast of polished and casual, then distressed jeans and a classic trench are a combo to add to your lookbook. For a Fall and Winter vibe, I finished the look with knee high boots.

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A woman wearing a classic trench coat in a light beige color.

A woman wearing a light beige classic trench coat with distressed blue jeans and boots.

6. Black Jeans with a Plaid Blazer and Crochet Scarf

Okay, I know I rave about blue jeans a lot, but I do like black jeans too! One of the biggest benefits of black jeans is that they can easily substitute for dressy pants. To create a look that straddles classy and casual, I opted for high rise straight leg black jeans from Levi's paired with a black turtleneck sweater and a plaid tweed blazer. That blazer delivers all kinds of sporty chic and cozy allure. To jazz up the look even more, I went for color-blocked square toe boots from Alohas and a contrastive yellow crochet scarf. This is an outfit that I wore to work and for casual outings and that's been marked as a favorite in my denim lookbook.

Shop the look here.

A woman wearing black ankle length jeans with a black turtleneck top and black and white plaid blazer. She has on color-blocked boots and a long yellow scarf.

Jeans are super versatile and offer so many options for creating looks that can go from work to happy hour to weekend errands. When paired with the right pieces, a simple pair of jeans can deliver maximum style. How do you like to style your jeans, and tell me, which one of those looks do you like the most?

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