Fall is finally here, and I’m ready to bring on the boots! There are so many great styles to choose from this season—and just as many (if not more!) trending jean silhouettes. It can all feel a bit overwhelming. But have no fear!Similar to my recent post on how to style jeans and loafers, today we’re walking through all the best boot styling options. I’ll share easy tips for pairing your favorite denim with the right footwear, how to choose outfits that complement each other, and examples of the best boots to wear with jeans this season. Let’s dive in!

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Tips on Styling Boots with Jeans

Before running through specific examples of which boots to wear with jeans, I wanted to share a few general styling tips and tricks. From my experience, these guidelines are helpful every fall and winter—no matter what the current trends may be.

1. Always Try On the Styles

When it comes to boots and jeans, I’m a firm believer that you need to physically try on the combinations. Two pieces might look great side by side or even on someone else, but you won’t know if they truly work for you until you’ve tested them together. A little experimentation goes a long way!

2. Play with Proportions

Finding the right proportions and styles that complement each other is key. When pairing jeans and boots, pay attention to the length, cut, and width of the denim—especially from the knee down—to ensure they work well together. In general, you don’t want your jeans to touch the ground. Instead, opt for cuts and boot heights that let the denim lightly graze the toe box of the boot or show a little ankle. Unless, of course, you’re styling skinny jeans—which I’ll cover a little further down!

3. Select Styles That Are Going to the Same Party

This saying is a little joke of mine, but it’s true—the boot and denim you’re wearing should feel appropriate for the same occasion. I don’t love pairing overly slick, dressy boots with casual denim, and I typically avoid wearing a casual boot with a more tailored pair of jeans. There are times I like to create a juxtaposition (like pairing dresses with sneakers), but a denim-and-boot combination usually isn’t one of them!

4. Stay in the Same Color Family

When deciding which boots to wear with jeans, be sure to envision the entire outfit—including your accessories. While I love experimenting with color (and there are so many beautiful hues to wear this fall), I usually try to stay within the same color family when styling boots. That often means avoiding mixing brown and black—though I do combine these in other outfit formulas!

For example, when I’m styling brown boots, I think about my tan and brown purses and whether I have a matching belt to complete the look. The same goes for black denim.

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4 Types of Boots to Wear With Jeans

Now let’s chat about some actual denim-and-boot combos I’m loving this season! I’ll break it down by boot style—booties, riding boots, lug soles, and stilettos—and highlight a few different jean cuts that pair well with each.

Booties

The bootie is a great style to start with. With a lower, tighter shaft, this boot can be styled in so many ways—making it one of the easiest types of boots to wear with jeans.

My personal favorite way to style booties is with cropped kick-flare denim. This combo creates a really pretty shape by showing the smaller part of your ankle. For example, this pair or this one would look great with cropped jeans. I also love the look of a sleek black bootie styled with black denim. You can see how I styled booties with kick flares last year here.

Wondering how to style wide-leg jeans? Try pairing a pointed-toe bootie with your favorite wide-leg to balance the silhouette. More of a straight-leg girlie? Chic booties look great with a comfortable straight-leg jean. Above I am wearing Veronica Beard booties (sold out similar here and here) with these straight leg jeans and this fun jacket. There are so many great ways to style this type of shoe!

Riding Boots

Okay, controversial take—but I’ll never get rid of my favorite skinny jeans. Gen Z can call them cheugy, but riding boots are the perfect example of why you should keep them around. Plus, you know they’ll come back in style—everything always does!

I’m loving the current equestrian trend, and one of my favorite ways to wear it is by pairing riding boots with skinny jeans, a turtleneck or button-down, and a tailored blazer. You can tuck straight-leg denim into riding boots, but that look just isn’t for me—I prefer a cleaner, tighter silhouette.

If you’re searching for new riding-boot options, I love these, these, these, and these! And if you want my look above I am wearing this blazer, with old Banana Republic riding boots (seen here) and my very old Current/Elliott skinny jeans.

Lug Sole Boots

The lug sole is one of the trendier types of boots to wear with jeans. I know this style isn’t for everyone, but it’s been growing on me this season. This is another reason it’s so important to actually try styles on and play around with them—you never know what might surprise you!

Lug-sole boots look great with cropped wide-leg jeans and flare jeans. I’ve been eyeing these boots, these, and these. Pair them with an oversized fisherman sweater for a cozy, cool fall outfit. P.S. You can check out my full guide to fisherman sweaters for even more outfit ideas!

Stiletto Boots

Stilettos are one of the trickier boots to wear with jeans. Because they have a higher shaft, you’ll want to ensure there’s enough room from the knee down for the boot to fit comfortably. Otherwise, you’ll need to commit to a skinny jean.

Personally, I like to save my skinny jeans for riding boots—not stilettos. Instead, I prefer pairing this style with wide-leg jeans or a mini skirt. I won’t go into the mini skirt styling in detail today, but I love the proportions created by a tall boot and a shorter hemline.

When styling stilettos with wide-leg denim, make sure your jeans don’t drag on the ground. Ideally, the hem should graze the top of the boot’s toe box for a clean, tailored look. These wide-leg jeans and these would both work well as long as they’re tailored to the right length. Some of my current favorite stiletto boots include these and these!

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Final Thoughts on Boots to Wear With Jeans

As cool weather approaches, I hope these tips and examples of boots to wear with jeans help you create easy, polished outfits for fall and winter. Whether you’re dressing up for a night out or keeping it casual for everyday errands, the right denim-and-boot combo can pull your entire look together.Remember, fashion should always feel fun and effortless—so play around with different combinations until you find your favorites! And if you’re building your fall wardrobe, you might also love my posts on how to style a fisherman sweater, loafers and jeans outfits, and colors to wear this fall.

September has finally arrived! Few fashion pieces signal fall quite like a timeless fisherman sweater. These intricate staples are historic, cozy, stylish, and, of course, perfect for layering. Naturally, they deserve their own post! Today, I’m diving into all things fisherman sweater—from their interesting history to my current favorites, including some unexpected modern interpretations I’m loving. I’ll also share outfit ideas and styling tips for pulling off the perfect classic look.

Shop the above looks here, here and here!

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Fisherman Sweater History

The fisherman sweater was originally created in the late 1800s on the Aran Islands, a cluster of islands off Ireland’s west coast. These sweaters were hand-knit by local artisans and made from untreated wool, which still retained some of the lanolin from the sheep. This natural element provided some protection against the harsh elements of the sea. Fun fact: if you can trace your family name back to Ireland, you might discover a specific stitch pattern that identifies your clan! Check out this page to see more of the beautiful clan knits.

Over the years, the definition of a true fisherman sweater has evolved. Today, designers and brands typically define this style as a thick knit sweater with detailed cable-like patterns.

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My Favorite Fisherman Sweaters & How to Style

Each fall and winter, many of my favorite heritage brands offer stunning traditional fisherman sweaters—and I’m already spotting plenty of them this season. But you know what excites me even more? The surprising, standout adaptations of these knits that put a fun, modern spin on a classic style!

Whether you’re a classic fashion lover leaning into timeless designs, someone who enjoys pairing an oversized sweater with jeans or leggings, or a fashionista looking to give fisherman sweaters a contemporary twist, there’s something for everyone. Let’s dive in!

1. Classic Fisherman Sweater

First up: the classic fisherman sweater—a timeless, effortlessly preppy piece with just a hint of old-money style. There’s so much to love about them. They’re incredibly versatile, pairing effortlessly with everything from jeans and loafers to leather pants for a more polished look. They’re also worth the investment: a well-made fisherman sweater from 15 years ago can still feel perfectly relevant today. And of course, we can’t forget the comfort factor—which is next-level cozy!

There are so many classic fisherman sweaters to choose from right now. I love the mélange coloring in this style, while this cozy cable turtleneck is perfect for staying warm. This gray fisherman sweater is currently on sale, and both this one and this one are such timeless picks. And if you’re on the hunt for a fisherman cardigan, the detailing on this one is absolutely beautiful.

How to Style

With a classic fisherman sweater—whether a crew neck or roll neck—I always opt for an oversized fit. To me, this maximizes comfort and plays into their historical menswear roots—the bigger, the better!

I often wear them alone or layered over a simple tee, but when it’s truly frigid, I like to add a turtleneck underneath or throw on an oversized topper. Because of the sweater’s volume, I recommend balancing it with slimmer bottoms: a slim pant, classic cord, or straight-leg denim pairs perfectly. For footwear, you can never go wrong with a classic loafer or a casual sneaker, like my trusty Sambas. I’ve previously shared tons of great loafers and jeans outfit ideas that are worth checking out!

2. Cropped Fisherman Sweater

After the classic comes the more modern takes! This season, I’ve been seeing a lot of shrunken and cropped fisherman sweaters, which perfectly align with current fashion trends. While these styles may not have the staying power of traditional silhouettes, they’re definitely fun to experiment with right now.

I love the shorter length of this chunky cable cardigan—it’s perfect for layering. And this chocolate brown fisherman sweater isn’t exactly cropped, but it’s also not oversized. It hits that perfect in-between fit that’s so easy to style!

How to Style

This wool-blend cable crew hits the perfect length—not too cropped, but not your standard fit. When styled thoughtfully, it can be incredibly flattering. Try layering it over a button-down shirt and pairing it with a mini skirt and platform heels. Finish the look with some fun jewelry for a playful, polished touch!

3. Colorful Fisherman Sweater

Fisherman sweaters are typically found in classic creams or natural shades like stone or light gray, which makes them incredibly easy to style. But if you’re looking to switch things up, there are some fun, colorful updates to consider!

In particular, I’m loving this sunflower-yellow knit version with a raglan sleeve. This cropped light-blue sweater is another great option—it pairs beautifully with all the vibrant hues that are right on trend and perfect examples of colors to wear this fall. Or what about this oversized overdye style, which comes in so many yummy shades that make layering and styling a breeze!

If you’re looking for a fisherman sweater that isn’t your standard ivory or gray—but also not too far from the norm—there are plenty of options. This cable roll-neck sweater comes in five colors (my favorite is the chocolate brown), and this oversized style is available in a timeless navy that works with everything.

How to Style

Styling options are much broader with colorful pieces compared to neutrals. Take, for example, this hot pink fisherman sweater. For a modern take, I’d suggest toning it down with a pair of light-wash barrel-leg denim. Complete the look with a pink pair of Chanel flats—like these or these—for a playful yet polished finish.

4. Feminine Fisherman Sweater

Another modern take on this classic style is pairing a fisherman sweater with a slip dress or skirt. This combo gives off super feminine vibes, making it perfect for fall. To pull off the look, I’d opt for a chunky, longer sweater—like this oversized cable knit. The timeless design pairs beautifully with a flirty bottom.

How to Style

So, which bottoms should you choose? This sweater looks stunning with a sophisticated dress or a silky slip skirt. For a casual vibe, complete the outfit with simple ballet flats. If you want to dress it up, swap the flats for a chic mule. When it comes to bags, I’d go for an understated option so it doesn’t overwhelm the look—like a Savette Pouchette or a simple clutch.

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Additional Styling Tips

While the outfit ideas above give specific inspiration, there are a few extra tips worth noting. These are general guidelines I like to keep in mind when hunting for the perfect fisherman sweater and dreaming up new ways to style it.

1. Don’t Be Afraid to Borrow from the Boys

If you love the oversized look, don’t hesitate to explore men’s fisherman sweaters. I often find that some men’s versions feel more authentic and traditional, which I love! For example, this men’s sweater is super chic, and this beige Aran sweater is truly timeless.

2. Layering Is Key

Because fisherman sweaters are so thick, layering can be tricky—but don’t let that stop you! I love pairing a tissue-weight turtleneck or a button-up underneath. Or better yet—both! If it’s super chilly and you need extra warmth, throw on an oversized jacket on top. Jackets with a drop shoulder work especially well here, giving you plenty of room for layering without feeling bulky.

3. Mix Materials for Depth

The cable knit already adds a ton of texture and visual interest, but when styling a fisherman sweater, think about the rich materials that would complement it. I love pairing them with suede, corduroy, waxed denim, leather, and even silk. Get creative, and don’t be afraid to push the boundaries!

4. Take Care of Your Sweater

This might not seem like a styling tip at first, but taking proper care of your fisherman sweater is absolutely essential—especially if it’s one you hope to wear for years to come. If a sweater gets stretched out, it won’t look good no matter what you pair it with. That’s why I always recommend folding sweaters neatly instead of hanging them, so they don’t lose their shape.

I share even more care tips in my sweater outfit post—from investing in a fabric shaver to properly washing your knits—so be sure to check that out!

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How to Wear a Fisherman Sweater with Ease

As cooler temps arrive and we start reaching for more layers, I hope these fisherman sweater styling tips help your outfits come together effortlessly. You really can’t go wrong with such an iconically classic style!

Be sure to check back for even more fall fashion inspiration as the season goes on. In the meantime, here are a few posts you might enjoy:

August 31, 2025

As I showed in my clothing color combination guide and in many of my daily outfits, I’m clearly a maximalist color lover. One of my favorite parts of every changing season is deciding which hues I want to add or expand in my wardrobe – and lately, I’ve got fall fashion on my mind. If you’ve been wondering about the best colors to wear this fall, you’re in the right place.

For this season, I always reach for the classics – deep browns, pretty tans, timeless navy, autumnal olive, and, of course, black. But I also like to have some fun by adding a “pop” color (or two!). Nothing excites me more than thinking about the new (or new-to-me) shades I want to experiment with. Today, I’m sharing the hues I’m most excited about, tips for mixing and matching, and simple ways to bring fresh color into your fall wardrobe.

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Top 5 Colors to Wear This Fall

Let’s jump right in and chat about my top five colors to wear this fall! These shades are in addition to the classics. While I love adding a bold pop of color—or even trying a full monochromatic look—the timeless autumnal hues and neutrals will always have a place in my fall color palette. They create the perfect backdrop, and the right unique color can be the finishing touch that makes any outfit feel fresh and current.

Robust Oranges & Bright Rust

While I probably have every color of the rainbow in my wardrobe, orange and purple are the shades I own the least. That said, I’ve noticed orange trending for fall 2025 – and I’m loving it. It’s the perfect transitional color: it gives off a cozy fall vibe while still feeling bright and cheerful, before the deeper, darker winter palette arrives.

This season, I’m especially drawn to orange paired with robin’s egg blue. I also love more tonal combinations, like red with orange or mustard with orange. It’s a bold yet wearable choice that instantly adds personality to your fall wardrobe colors.

Teal & Light Blues

When it comes to cool tones, I’m all about a deep, beautiful teal or a brighter, happier light blue. These shades pair perfectly with many of the colors to wear this fall. Light blue with red makes a stunning combo, while teal with maroon creates such a lovely match.

Over the years, I’ve collected quite a bit of teal jewelry – many pieces you can spot in my Dorsey jewelry post. I’m especially excited to experiment with adding those accents to my fall wardrobe.

Chartreuse

Pops of chartreuse have been trending for a while, as I showed in my green outfit ideas post. And its popularity only continues to grow for fall 2025. The shade feels vibrant yet moody, which makes it the perfect autumnal hue.

One of the reasons I love chartreuse is how versatile it looks across different fabrics. From an elegant silk to a fluffy, cozy mohair, this hue adapts beautifully. I’ve recently styled it in a dress-and-jacket look, as well as a playful printed outfit. And I can’t wait to keep incorporating this shade into upcoming looks.

Maroon

Maroon, oxblood, burgundy (call it what you want) this color is always a must-have for fall dressing. I’m especially excited to incorporate the darker, deeper reds that are trending for 2025 into my wardrobe. This shade is magical when paired with a timeless tan or mocha brown, but it also looks amazing alongside red or even chartreuse.

Honorable Mention: Mustard Yellow

Yellow can be a tricky shade to pull off, but when styled correctly, it’s such a fun hue to wear. The deeper, richer tones of yellow are especially great colors to wear this fall. These shades feel more sophisticated, and the darker tone allows them to pair effortlessly with brown, tan, and navy. Mustard yellow can even add a collegiate vibe to a preppy look—which, as you know, I’m loving this season!

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My Favorite Combinations of Colors to Wear This Fall

Now that we’ve explored some of my favorite autumnal hues, let’s talk about pairing these shades together. While a monochromatic look can give off a classic old-money style vibe, most of us don’t stick to just one color or only neutrals for every outfit. With so many gorgeous fall shades, it’s fun to add a pop of color or mix a few complementary hues. Here are three color combinations I’m most excited to experiment with this season.

Orange + Tan

The combination of orange and tan feels like a fall dream. This warm, inviting pairing makes orange much easier to pull off. I especially love when two warmer hues play off each other, creating a smooth transition between colors. Because the shades aren’t as contrasting, don’t be afraid to mix materials and textures with this duo to add extra interest to your look!

If you’re not into the monochromatic approach and want to take more of a risk, try a deep orange with light blue. Or, if you love a tone-on-tone look but want a bit more zing, pair orange with red for a fun, unexpected twist.

Maroon + Teal

Next up is a vibrant combo with some zest: maroon and teal! Compared to orange and tan, this pairing is bolder, yet it still feels elevated. Both tones are inherently sophisticated, so even though it’s a pop color on a pop color, the look still feels elegant.

Want something a bit more feminine to pair with maroon? Try a soft, dusty pink for a subtle, chic twist!

Mustard Yellow + Navy

As I mentioned, I’m currently loving everything that gives off preppy, collegiate vibes. Mustard yellow and navy are the perfect colors to wear this fall to capture that trend. When styling this pairing, I love adding classic touches of gold—like gold buttons—to give the outfit a little extra dimension.

Not into the preppy look? Try pairing mustard yellow with olive green instead. This is another very autumnal, yet wearable, combination.

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4 Easy Ways to Incorporate Fall Colors Into Your Outfits

Combining shades or adding a bold color pop can sometimes feel intimidating, but there are so many fun ways to do it! You could add a pop of color to your favorite animal-print outfit, give an old-money style look a unique twist with an unexpectedly bold lipstick, or simply add a colorful pair of loafers to your favorite jeans and tee.

If you’re looking for a few quick, easy, and specific ways to bring color into your fall wardrobe, I’m sharing four ideas below. While they’re all simple finishing touches, sometimes these small additions can make a big difference!

1. Add a Colorful Accessory

There’s no easier way to add a pop to an outfit than with a colorful accessory. My go-to is a vibrant bag, but it could also be a statement necklace, bold earrings, or even a wide belt. For fall specifically, don’t forget scarves, baseball hats, or gloves. One of my current favorite ways to add color with accessories? Chunky bangles—they instantly make an outfit feel fun and there are so many colorful options!

2. Add Colorful Tights or Socks

One of the most inexpensive—but powerful—ways to add an extra hue to your outfit is with colorful tights or visible socks. If you really want to make a statement, you could even layer colorful tights with socks or knee highs in a contrasting shade. I’m also loving the loafers-and-socks combo this fall—a sweet, ruffled sock in a fun color paired with a classic loafer is such an easy and playful way to experiment with fall wardrobe colors.

3. Play with Layers

The more pieces you wear, the more opportunities you have to try out new colors for fall, right? Some easy layering options include draping a coat over your shoulders, tying a sweater around your neck, or even experimenting with the trend of layering two cardigans together! Back when I was living in San Francisco, I became a layering expert out of necessity—and to this day, experimenting with layers is still one of my favorite ways to explore fall styling.

4. Don’t Forget Beauty Products

While this option isn’t always the most obvious, colorful pops from beauty products can make a big impact on your outfit. These touches pack a lot of punch with very little investment. For example, you could paint your nails in a fun fall hue or try a bold new lipstick. Personally, I’m loving orange lipstick right now—it feels like the perfect way to add color to my pre-fall and fall outfits!

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Final Thoughts on Colors to Wear This Fall

Autumn is the perfect season to have fun with your wardrobe and experiment with new hues. From rich maroons and teals to bright oranges and mustard yellows, there are so many beautiful colors to wear this fall. Experiment with mixing shades, layering textures, or adding colorful accessories to create a seasonal look that truly feels like “you”!

For more fall fashion inspiration, be sure to check out these posts:

August 4, 2025

So July flew by. As we enter the month of August, I must admit that from a retail perspective, I always seem to dread this time of year a bit. Summer is still very much summer-ing but retailers and media outlets have already started the *it’s fall* conversation. It’s one of those strange cuspy times where I feel like I am being pushed into the next season too quickly. Please let’s just enjoy the end of summer!

I am starting a new series at the end of each month looking back and highlight some of my favorite posts, looks, purchases and more from the previous month. ICYMI aka In Case You Missed It! July I posted quite a bit – 32 new outfits, 27 new posts, and over 150 product picks. Let’s dive into some of what you may have missed.

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PRICE POINTED FINDS // You all love when I post items that fall under $200. And I get it – I also love to find cool, new pieces at great price points. This month I rounded up my favorite fashion finds under $100 here and under $200 here.

STYLING 101 // I am constantly trying to bring value to you beyond shopping round ups and outfits. I am so grateful for the positive feedback I have gotten on writing more posts geared towards styling or how to wear trends. This month I focused on shirt dress styling and how to capture the old money trend.

LITTLE THINGS TO LOVE // Sometimes it is nice to have posts where I can freely share what has been on my radar or bringing me joy without a ton of structure. July I reallllly embraced this because I wrote not one, but two little things to love posts (which is another series you seem to love). You can peek them here and here. I also started a new post series this month and did my first two posts here and here and here. These are more about what I am seeing in the market, what I am eyeing, and what makes me excited in the current the season.

SOME LOOKS TO LOVE // My personal favorite looks for July, while it was hard to narrow down, have to be this look, this look, this look and this look.

LINK LOVE // Knowing what you all connect with is always so fun to see. Each month I am constantly tracking what you are clicking on the most and what you are purchasing. You all loved this blazer, this dress, these shoes, and you went crazy for this incredible sample sale – which FYI is still going on!

COMING UP IN AUGUST // I have quite a bit coming up in August. There will be some NYC content, lots of sale round ups (I do love a good end of season sale), more styling 101 posts and much, much more. So, stay tuned!

July 24, 2025

Simon Miller Top, Xirena Pants, Valentino Hat (old, similar here), Margaux Sandals, Chan Luu Tote, Prada & Vintage Necklace (similar here and here), Saint Laurent Sunglasses

There’s something grounding about a good try-on in the morning light when everything feels a little quieter and more clear. It’s the best time to take stock of what’s new and see what actually works beyond first impressions. This week’s edit is a mix of fresh arrivals that immediately felt right and a few unexpected standouts.

Rosie Assoulin Top, Loewe Jeans, Vintage Necklace (similar here), Bottega Veneta Bag, Amanu Sandals

This crisp white cotton mini dress combines a structured shirt collar and button-down front with a subtly flared A-line skirt. Pair with flats and a textured bag for sophisticated yet understated style. 

A chic and functional accessory ideal for both daytime outings and evening events, this gorgeous bucket bag features woven raffia and cane with calf leather accents.