6 Versatile Shoes That Go With Different Jeans Styles to Wear This Winter

6 Winter Shoes That Go With Different Cuts of Pants

Which pair of shoes to wear with which pair of jeans has always been a popular question from the PMT community, and it’s an even bigger issue thanks to the variety of denim cuts that are now popular. Add to that the fact that it’s winter, which makes your shoe choices more important (and limited), and figuring out which shoes with which jeans is more trouble than ever! Today I hope to make your life easier by sharing 6 versatile pairs of shoes that go with different cuts of jeans so you have some options that are both functional and stylish.

Before we begin, I want to remind you of several CRUCIAL factors for making shoes work with jeans. For the most VERSATILE and effortless pairings, there are several things you MUST be mindful of! Make sure the LENGTH of your jeans is CORRECT and make sure your shoes have a couple of key characteristics. Find these guidelines in How to Wear Shoes With Jeans in Different Cuts – 4 Best Practices. If you don’t do these things, pairing shoes and jeans will be really difficult.

Okay, with those tips in mind, here are 6 pairs of versatile shoes that go with different cuts of jeans!

SIZING: I’m 5’6” and usually S/M or 6 in clothes and 8.5 to 9 in shoes.


black sweater + flare jeans + ivory cardigan sweater + green plaid shirt + girlfriend jeans + tan boots + gold jewelry

1. Naturalizer Water Repellent Boots
These are my go-to boot options for casual style with jeans, sweatshirts, and relaxed sweaters. The lug sole is very casual, so it works in these super casual outfits.

These boots are water resistant, too, which is another reason they’re on my go-to list. When it’s raining and we are walking our kids to school, I love being able to throw these on like it’s any other day and NOT have to think about whether I need to wear rain boots and change my entire outfit to work with the rain boots!

These work seamlessly under my LC Lauren Conrad flares, my twill wide leg pants, my Old Navy wide leg jeans, my ankle-length kick flares (similar HERE) because the leg openings of all of those pants are wide. They also work great with girlfriend jeans rolled up to sit on top of the boot shaft.

These are available in 4 colors, HERE. I wear size 8.5.

Shop the Outfits:


blue balloon sleeve sweater + ivory wide leg pants + green sweater + slim jeans + black and white striped tee + camel cardigan sweater + kick flare jeans + camel heeled boots + gold jewelry

2. The Drop Boots
These are one of my go-to dressy boots. They are polished and look great in dressy casual outfits with jeans as well as all work outfits! The square toe elongates your leg line and adds a polished touch to outfits. The shaft of the boot is really tall and very narrow, so it works super well under all cuts of jeans. Above, I’m showing these boots with a variety of pant widths and lengths, from a super slim pair of straight leg jeans to wide legs, and even a pair of ankle-length kick flares. Notice that my ankles are still covered thanks to the tall shaft! These are definitely among those at the top of the list in terms of shoes that go with different jeans because of how tall and SLIM that shaft is.

(Pro tip: When shopping for the most versatile boots, always test to see if they will fit under your slimmest pair of straight ankle length jeans or pants. If they are tall enough to fit under ankle length pants and narrow enough to fit under your slimmest pair, they will most certainly work with all the other cuts like flares and wide legs, which are wider than slim straight pants.)

Find them in 5 colors, HERE. I wear size 9.

Shop the Outfits:


black moto jacket + black tank + red and white printed top + slim jeans + black balloon sleeve sweater + ivory pants + black belt + black floral top + black pintuck pants + gold jewelry + black kitten heel boots

3. Gap Pointed Toe Kitten Heel Boots
This is my other pair of go-to dressy boots. Really, between this pair and The Drop pair above, I feel like 99% of my dressy needs are taken care of. So versatile!

I usually stay away from really pointed toe boots as they feel too dressy for me on a day-to-day basis. But, when I want to really sharpen up a look, like for special occasions or night-out looks, I welcome the pointed toe. The point on this pair isn’t too long either, so I don’t feel like I’m wearing elf shoes. 😆

This pair has a tall and narrow shaft that works under lots of different cuts of pants, which is why it’s on the go-to list. The heel is pretty low, so it is really easy to walk in. I know a lot of people look at a skinny little heel like this and think there’s no way they could walk in it, but I usually find that a shorter heel like this feels pretty sturdy and is not a problem. (If it were a skinny heel AND 2” or 3” tall, then I would definitely be worried about rolling my ankle, though!) Find them HERE. I wear size 9.

As much as I like these shoes, do not buy them at full price and definitely wait for one of Gap’s regular sales instead!

Shop the Outfits:


tan sweater + black wide leg jeans + gold cardigan + graphic tee + cropped light wash jeans + ivory pullover + black leggings + black and white sneakers + gold jewelry

4. Lifestyle Sneakers
Yes, it’s winter, but in some places we can still wear lifestyle sneakers on some days, so they’re on the list!

Lifestyle sneakers with a low profile can completely transform your casual outfits from dull to stylish and make you feel more put together in an instant. There are MANY sneakers to choose from that would be versatile and look great, so I’ll highlight some below.

Personally, these Dolce Vita Zina sneakers have been my go-to sneakers. They work well with all ankle-length jeans in everyyyy single cut, (talk about shoes that go with different jeans)! They look cute with my LC Lauren Conrad flare jeans, my twill wide leg pants, my flare leggings, and my joggers—as long as the LENGTH for all of those pants is correct!! That includes your joggers, which NEED to hit at the ankle-length sweet spot mentioned above to look good!

Aside from the style with the black and metallic accents, I also really like two things: 1) there is a tiny little wedge inside that tilts your leg ever so slightly and helps elongate your leg line just a bit. And 2) it has a lower vamp, i.e. the tongue doesn’t come up as high or as close to your ankle, which also helps elongate your leg line. For me, with fuller calves and skinnier ankles, if the tongue comes up too closely to my ankle, it will cut off my leg line. It is hard for me to find sneakers with a low vamp, but it’s a top priority for me, personally! See them in tons of colors, HERE. I wear size 8.5.

BTW, these really molded to my feet after a while. Honestly, when I first got them, they rubbed my toe the wrong way after too long of wear. But eventually, the shoes completely molded to my feet. I now wear them with ZERO issues, including walking ALL DAY for 2 whole weeks around a busy city like Hong Kong.

Now, like I said, there are lots of options for low-profile lifestyle sneakers. If you like something more classic, I also recommend these Dr. Scholl’s slip-on sneakers. (Also available in more colors and sizes HERE.) They are SUPER comfortable. These also have a lower vamp, which helps extend my leg line and makes it look better with ankle-length jeans and with skirts and dresses.

Another option is the Cole Haan sneaker, which one of our PMT teammates absolutely loves.

Shop the Outfits:


5. V-Italia Water-Resistant Wool-Lined Boots (Snow Option)
I don’t own these, but I wanted to offer snow-appropriate versatile shoes that go with different jeans, so I asked one of our PMT teammates, Crystal, who lives in a super cold area for her rec. The exact pair she owns is limited in stock (HERE), so the pair shown above (and found HERE) is a similar option from the same brand. These boots have removable wool insoles, have non-skid outsoles, and have treated water and salt resistant leather. Crystal likes that the lining is actual wool, so it’s warmer, and that these are genuine leather. I also like how the shaft is high and fitted, which helps them fit under a variety of jean styles.



6. Cliffs Hiker Style Bootie (Snow Option)
This is Crystal’s other recommendation for snow. These are much more affordable than the V-Italia shoes, but therefore, there’s a difference in quality. For instance, these are not genuine leather, and the cozy lining is not wool. But still, Crystal says, “I own these, and I’ve worn them a LOT! They’ve held up well, and they also perform well in snow. They don’t get wet easily and are quite warm. I’ve worn them with several different styles of denim.” Good if you’re looking for something more affordable! Find them HERE.


tan sweater + girlfriend jeans + black boots + gold necklace + gold earrings

Runner Up #1: Caslon Water Resistant Miller Boots
I really, really like these boots. Like the Naturalizer boots in #1 above, the lug sole works so well in super casual outfits with relaxed sweaters and sweatshirts, and it works in slightly nicer casual outfits, too, like with a plaid shirt and a cardigan. The leather is really soft, and these boots are very comfortable! They’re water resistant, too!

However, the reason these boots are only a runner up and not included in my go-to options is because the shaft is a bit low. So, when it comes to ankle-length jeans, these don’t work as seamlessly and with as many different cuts as the Naturalizer boots do, which have a taller shaft. The best way that these work with ankle length boots is if you have a skinny, straight leg, or girlfriend cut that can be rolled up to sit on top of the shaft. But they don’t work with flares or wide leg jeans that are ankle-length. Other than that, these boots are great. Find them in several colors, HERE. I wear size 8.5.


kick flare ankle length jeans + black textured sweater + brown chelsea ankle boots by kenneth cole reaction

Runner Up #2: Kenneth Cole Chelsea Boots
This is a great pair that’s between casual and a little dressier, so Elevated Casual. The toe box is elongated but not super pointy, so you don’t feel too overdone in it, but it keeps your leg line long in full length flares, bootcuts, and wide leg jeans. The shaft is really tall and narrow–here I’m wearing it with ankle length kick flare jeans, and you can see that my ankles are totally covered. Most importantly, the heel is lower than the other nicer heeled boots here, so they are easier to walk in through out the day.

The downside, and the reason they are just a runner up, is because they are not water resistant. Otherwise, they’re really versatile and work with lots of cuts of jeans. They come in 6 colors, including some suede options, HERE! I wear size 9.


That’s it for versatile winter shoes that go with different jeans! I really hope this makes it easier for you to pair shoes with jeans and helps you get dressed more quickly and EASILY each day!



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