12 Ways to Style Brown Boots & Booties – Simple & Chic Outfits Over 40

12 Ways to Style Brown Boots and Booties

I LOVE brown boots and booties. Don’t get me wrong, I also love black boots and booties…but with my style, I tend to gravitate more toward lighter, neutral color palettes with beautiful beiges and yummy brown tones. No matter what your style, brown boots are a must-have in every woman’s closet. They’re a wardrobe basic that is crucial to building all of your fall and winter (and even some spring and summer) outfits for those colder months! They’re super stylish and versatile, can be dressed up or down to suit your mood or occasion, and there are TONS of options out there. Keep scrolling to find SIX ways to style your brown booties that are casual and dressy! Most of these outfits are older and sold out but you can still get plenty of inspiration!

If you’re looking for more brown boots outfit ideas, make sure you check out this post too!

Ways to Style Brown Boots & Booties

Do Brown Boots Go With Everything

Brown boots and booties are so classic and versatile that they really can go with everything. There are so many different types of brown boots out there that no matter what you’re wearing, there’s probably a boot that you could pair with your look. Depending on the type of brown boot or bootie, you can wear them with dresses, skirts, or jeans in all styles. If you don’t already have brown boots in your closet, make sure you consider the different shades of brown that will work with your wardrobe, heel heights that will work with your lifestyle, shaft heights that will work with your bottoms, and materials (like leather, suede, etc.) that you prefer.

Below, I’m sharing six outfit ideas to give you some inspiration to recreate outfits from pieces you have in your closet.


Ways to Style Brown Boots and Booties

#1) Brown Booties with Straight Leg Jeans

The first look is a classic casual outfit combination that really can’t go wrong. A sweater + jeans + brown booties = a super easy and chic fall/winter outfit! You can recreate this look with any pieces in your closet, but I’m wearing a Fair Isle sweater by Brochu Walker that is SO soft, comfortable, and cozy. And the colors in it are just so beautiful!
I styled the sweater with a pair of AG jeans I’ve had for years and wear all the time. They are straight-leg, super high-rise, and SO easy to style with any kind of shoes.

On my feet, I’m wearing an old pair of brown Paige booties I’ve had for years. I love the way to brown boots complement the brown tones in the sweater…perfection! But you can wear whatever brown booties you already have in your closet. Since these jeans are a slimmer straight-leg fit, I could also wear some brown knee-high boots too. If you don’t already have brown booties, I linked a similar pair below.

Ways to Style Brown Boots and Booties with a Dress Brown Boots with a Dress outfit

#2) Brown Boots with a Dress

The next way to style your brown booties is with a mini dress! This is s super simple combo. Because this dress is short, the length is easier to style with boots and you can get away with pretty much any style of brown boot…ankle, high-heeled, knee-high, combat, sock booties, etc. Throw on an oversized teddy coat, and some of your favorite everyday jewelry, and you’re ready to go!

If mini dresses aren’t your style, you could also style your boots with midi dresses, maxi dresses, flowy dresses, sweater dresses, etc. If you wanted to dress this look up even more, you could swap the block-heel boots for a pair of brown boots with a stiletto heel. The possibilities really are endless!

I love a boots and dress outfit combination so much, I shared 12 ways to wear boots with a dress here.

casual holiday outfits

#3) Brown Knee-High Booties with a Printed Dress

If you liked the last look, this is another great option and it’s a little dressier. I’m wearing a printed chiffon dress by Paige that has the prettiest geometric pattern and flattering v-neckline. This is one of those dresses that can be dressed up or down. I chose to style it with a pair of dark chocolate brown stiletto booties by Schutz. I have these boots in black, ivory, and python as well, and talk about how much I love them all the time…just trust me, they’re great!

Brown Booties with Black Dress

#4) Brown Booties with Black Dress

If you want to turn up the sexy for your next date night or GNO, this brown bootie outfit is the one for you! The dress I’m wearing by ASTR the Label is a sexy show-stopper. The longer length is ideal for women over 40 but I love the fitted silhouette and strappy cutout details on the bust. You don’t need this exact dress to recreate this outfit…but if you’re looking for a new black dress, this one is perfect! I’m wearing the same Paige booties, but you could also wear a pair of brown ankle boots, black booties, heels, sneakers, sandals, etc.

knee high boots winter dress

#5) Brown Knee-High Booties with a Brown Dress

Here’s another sexy dress option. This Norma Kamali dress has a sexy high-low length and super flattering ruching. It’s in a gorgeous brown that pairs perfectly with those Schutz brown stiletto booties you saw in a previous look. This is such a cool outfit and I love that it’s monochromatic. If the fitted dress isn’t your style, swap it for a midi or maxi-length sweater dress with a more forgiving fit…easy peasy!

what to wear with brown boots Brown Boots with Chino Pants

#6) Brown Boots with Chino Pants

This is probably the most unique way I’ve come up with to style brown boots…and I LOVE it! This Frank & Eileen button-down shirt is super high quality, has a beautiful fit, is very well-made, and the fabric is amazing.
I paired it with a pair of Frank & Eileen chinos that are equally as high-quality and well-made as the shirt. I’ve been throwing these pants on with different tops and sweaters and finding it fun to try them with different, unexpected pieces. When you think of chino pants, you think of them in a more traditional way, styled with sandals or mules, but I love them with western boots and a glam teddy coat. This is just a really cool look for any of my risk-taking fashionistas out there!

Brown Booties with Baggy Jeans

#7) Brown Booties with Baggy Jeans

This next look is another great, casual option that you can tweak depending on your personal style preferences. I’m wearing the same brown Paige booties from previous looks underneath these cool, baggy high-waisted (11”) jeans by SLVRLAKE. I love that they’re a baggier fit but still pretty straight-leg. They fit beautifully over my booties and will work perfectly with whatever brown ankle booties you have too! The length is great on me when I’m wearing heeled booties but if you’re shorter (I’m 5’4”) you might need to get them hemmed.

By the way, if baggy jeans aren’t your style, that’s OK! This look would work with skinny jeans, straight jeans, flared jeans, ripped jeans, or whatever style you feel comfortable in. I styled the jeans with an IRO sweater with the most gorgeous details like the puff sleeves, unique ribbing, and shorter hemline that takes the guesswork out of whether to tuck it or not. I love wearing this sweater with high-waisted jeans.

Banana Republic blue sweater and jeans

#8) Brown Ankle Booties with Ripped Jeans

The rest of the outfits in this post will ALL be jeans so if you’re looking for ways to wear your brown boots with jeans, you’ll find plenty of inspiration! In this look, I’m wearing a pair of older ripped jeans that are super distressed and give the look an edgier feel. But if you don’t like ripped jeans, just go with a classic pair of straight-leg jeans instead. On my feet, I’m wearing a pair of brown suede western-inspired booties by Dolce Vita. I completed the look with a fun pop of color on my top half with this pretty cobalt blue sweater from Banana Republic but again, you can make modifications, wear a different color, or opt for something more cropped or body skimming. Make adjustments for YOUR style!

If you’re wondering what shoes to wear with what kind of jean styles, make sure you check out this post next. It has a really helpful graphic and tips!

Brown Knee-High Boots with Skinny Jeans

#9) Brown Knee-High Boots with Skinny Jeans

With the baggy jean trend still going strong, I often get asked if we should still hold on to our skinny jeans to wear with our knee-high boots. And the answer is yes! While it’s on-trend to tuck baggier jeans into knee-high boots, it’s a pretty fashion-forward look and much easier to opt for skinny jeans. In this look, I’m wearing a pair of classic dark wash skinny jeans with some knee-high, block-heel booties by Schutz that have a cool western vibe and flattering pointed-toe. I completed the look with a white blouse and faux fur jacket, but you can wear a sweater, button-down, tee, moto jacket, cargo jacket, bomber jacket, etc. too.

Knit Booties with Flared Jeans

#10) Brown Knit Booties with Flared Jeans

Another way to wear your brown booties is with a pair of flared or bootcut jeans. This is a super simple look that’s very similar to #1, but swapping to straight-leg jeans for flared or bootcut jeans can be more flattering on some body types. In this look, I’m wearing a pair of dark-wash bootcut jeans by AG, a white ribbed sweater from Anthropologie, and some really cool knit lug-sole booties by Steve Madden. This is a classic look and SO easy to recreate!

Thanksgiving outfit ideasstaud layered sweater dress

#11) Brown Stiletto Booties with Pre-Layered Sweater Dress & Jeans

This last look is actually a 2-in-1…On the left, I’m wearing a pre-layered Staud sweater dress on its own with some stiletto booties to show you how you can really dress up a sweater dress with some sexy brown booties. On the right, I took the same sweater dress and styled it with the same booties but also added a pair of straight-leg jeans! This makes the look feel more casual and also gives you some leg coverage since that sweater dress is a little short.

Brown Booties with Joggers

#12) Brown Booties with Joggers

This last look is another one for my trend-setting fashion lovers…Brown booties over a pair of baggy joggers! Wearing boots over baggy jeans, trousers, joggers, pants, etc. is very on-trend right now so I wanted to give it a try. I’m wearing a pair of Rag & Bone joggers that look like jeans. They are SO comfortable and feel like lounge pants, but they have the look of real jeans printed onto them…cool, right?! A few Team Busbee members purchased and LOVE them too, which means they’re good for multiple body shapes, heights, and styles. If these are too trendy for you, swap them for your favorite pair of jeans to get the same look. I styled the joggers with a pretty brown plaid blouse by Isabel Marant. I love the plaid print, puff shoulders, silver buttons, and overall western-inspired look.

Which brown boot outfit was your favorite? Let us know in the comments below!

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