Figuring out what jeans to wear with boots with can be a bit tricky, especially when there is so much style advice out there. To tackle this I’ve created a guide that answers the question for a whole host of different jeans and boot combinations, to make sure all bases are covered.
What jeans do you wear with boots?
Wear skinny jeans with any kind of boots and they will look great – especially with over the knee boots and sock boots. Wear straight leg jeans over boots that are fitted to the calf and wear baggy or mom jeans with heeled ankle boots to elongate your legs and balance your outfit.
Different boots and jeans combos apply for the changing seasons, and for day-time and night-time outfits:
- For day time outfits pair tan boots with indigo or light wash jeans. Alternatively pair black boots with light wash jeans.
- For night time outfits opt for a darker wash jean to pair with black boots.
- In spring/summer pair lighter boots with lighter jeans.
- In autumn/winter pair your darker coloured jeans and boots together.
Now you know the basic rules for pairing jeans and boots, let’s breakdown different styles of boots with different jeans in pictures, for style inspiration.
Cropped jeans with chunky boots:
Wear cropped or cuffed jeans with Dr. Martens boots to show off the boot and to not bulk the ankle and calf by trying to cover them by putting the jeans over the top. Dr. Martens or other style of chunky boots also look great with skinny jeans tucked in.
The rule with these kinds of boots is to show them off, so make sure you’re either tucking your jeans in or rolling up the cuffs to meet the top of the boot, instead of trying to wear them under your jeans. You could also wear baggy high waisted jeans with this type of boot, as long as you cuff them and wear a more fitted top or jacket to balance out the look, for a modern trendy style.
Skinny jeans with sock boots:
With sock boots it’s best to wear them with skinny jeans, to create a seamless look. Sock boots traditionally look best over the top of skinny jeans, but you could also wear them underneath if you wish, as they are so fitted they won’t bulk out your ankles and calves.
All kinds of sock boots look great with skinny jeans; velvet (as pictured above), suede, or more plain fabrics. You can pair different washes of skinny jeans with your sock boots, although I typically prefer to pair them with black or dark wash skinny jeans, such as indigo wash, to elongate the legs.
Heeled sock boots work best with skinny jeans to create a streamlined silhouette.
The same rules apply for over the knee and knee-high boots; pair them with skinny jeans to create a well fitted look. Pairing over the knee or knee-high boots with any other kind of jean will look odd, as the material will bunch and the legs will look bulky.
Mom jeans and black ankle boots:
Mom jeans pair really well with black ankle boots with a heel, for a trendy 2021 style. I paired my light wash mom jeans with two kinds of black ankle boots, to show how nicely the two go together.
With my gold heeled ankle boots I dressed up the mom jeans, along the with a floral top and a bag. To keep it more casual, pair mom jeans with black ankle boots with a plain heel, for a day time look.
Mom jeans look great with taller ankle boots, as the hem of the jeans tends to meet the top of the boot. If you mom jeans are too long, instead of tucking them in just roll up the cuffs slightly until they meet the tops of the booties.
Skinny jeans and taller ankle boots:
Wearing tall ankle boots with skinny jeans is a great way to showcase the boot and elongate your legs.
I love this pairing, as it looks so streamlined and elegant. It also works well for both day and night outfits; just switch out your top and bag for dressier options and you are ready to hit the town.
Above I paired tall black ankle boots with black skinny jeans and with tighter fitting skinny mom jeans, to show this effect. With black skinny jeans and black taller ankle boot you can tuck the jeans into the boot for a seamless finish. Alternatively you could cuff the jeans if you wish.
Baggy jeans and heeled boots:
Pair baggy jeans with heeled boots for a 2021 style look. The heeled boots with elongate your legs and balance your frame, whilst the high waisted baggy jeans add a pop of trendy style.
The pairing looks great together for both day and night outfits. Just make sure you wear a closer fitting top for your top half, to balance the outfit, as I styled above. Of course there are no rules with fashion, so style this however you like, but I find a tighter top looks great with this jean and boot pairing.
Light wash and dark wash baggy jeans pair really well with heeled black boots, so have a look through your wardrobe and try styling the options you have.
What jeans to wear with women’s Chelsea Boots?
Wear skinny jeans with Chelsea boots to elongate the legs and show off the boots without bulking the ankles. Chelsea boots also look best with cuffed or slightly cropped jeans, for a trendy style.
Alternatively chose a jean with a distressed hem that meets the top of the Chelsea boots, for a trendy look. Mom jeans also pair nicely with Chelsea boots, as long as they are cuffed and don’t bulk over the top of the boots.
Wear a chunky fleece jacket with your mom jeans and Chelsea boots for a cool and trendy look. In summer/autumn pair your mom jeans with a crop top and Chelsea boots for a laid-back chic style.
What jeans to wear with ankle boots 2021?
Wear skinny jeans with ankle boots in 2021 for a modern style. Tuck the jeans into the boots so the denim doesn’t bulk around the ankle. You can also pair ankle boots with mom jeans with a distressed hem for a trendy look.
Ankle boots and skinny jeans are a classic pairing that look instantly put-together. They can look casual when pair, or can be dressed up for an evening out.
For a day time look pair tan ankle boots with indigo wash skinny jeans, a white tee or cream turtleneck and neutral toned jacket or cardigan, as pictured below. For a night time look pair black ankle boots with black skinny jeans and a nice top or bodysuit, with a tailored jacket, for a smart casual, polished look.
Can you wear boots with straight leg jeans?
You can wear boots with straight legs jeans, as long as you pair the right kind of boots with the jean. For example heeled boots that fit under straight leg jeans look best, as they will elongate the leg. Pair a boot that fits closely to the calf to avoid bulking.
Choose a straight leg jean with a shorter hem, so they don’t completely cover the boot, and choose a boot with a higher shaft so no part of your ankle is showing. This will create a more streamlined look, as a bit of ankle showing can look odd with straight leg jeans.
Should jeans go over boots – women’s?
Women’s jeans can go over boots or can tuck into boots depending on the style of jean. For straight leg jeans, wear them over your boots, as long as the boots fit closely to the calf. Tuck skinny jeans into boots, for a comfortable fit.
For chunky boots wear either cuffed or cropped jeans that meet the top of the boot, or wear skinny jeans and tuck them into the boot. When pairing boots with straight leg jeans choose a jean with a slightly shorter hem, so some of the boot with show for a more tailored style.
Do you tuck skinny jeans into ankle boots?
Skinny jeans can be tucked into ankle boots for a streamlined effect that elongates your legs. Skinny jeans look best tucked into ankle boots, so the material doesn’t bulk when forced over the top.
If you try to wear your ankle boots under your skinny jeans the material with bunch and stretch, which may ruin the hems of your jeans. This also doesn’t look very polished, and can make the calves or ankles look bulky. If in doubt, pair black ankle boots with dark wash or black skinny jeans and tuck them in for a polished look.
Alternatively if you have tan ankle boots, pair them with an indigo wash jean, and either cuff the hems for a trendy look, or tuck them in.
What kind of boots do you wear with skinny jeans?
You can wear just about any kind of boots with skinny jeans, as they are a versatile jean that pairs great with most shoes. Make sure to tuck your skinny jeans into your boots instead of wearing them over the top, as this will bunch the material. Alternatively, cuff the hem of your skinny jeans to meet the top of your boots for a trendy look.
Knee-high and over the knee boots should always be paired with skinny jeans. Likewise ankle boots, sock boots, cowboy boots, Chelsea boots and chunky boots all look fantastic with skinny jeans tucked in, as this style of jean elongates the legs and shows off the boots.
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Thank you for reading this boots and jeans style guide, and I hope you now feel confident to pair your footwear to your denim! Remember there are no rules in fashion, just guidelines, so pair your boots and jeans however you like and with what feels comfortable for you.
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Lorna is a footwear geek and the founder of Wearably Weird. She created a YouTube channel in 2021 for fellow footwear fanatics, dedicated to detail-rich footwear reviews and info. She has a fashion media qualification (awarded in 2011).