The Ultimate Guide To Styling Jeans With Fall Shoes
What denim silhouettes should you pair with what shoes? Plus, what styles I'm recommending!
In styling sessions, I’m often asked by clients about shoe and jean combinations. From straight leg to skinny to barrel to wide leg, the options can be overwhelming! So that’s why in this newsletter (and in my new YouTube video!) I’m breaking down every denim silhouette, how to style them, and the shoe pairings I recommend for each.
Styling & Fit
The Barrel silhouette is excellent if you want a relaxed and casual fit, but you like a pant that is slightly more tapered at the bottom. A lot of clients find that it’s easy to pair with a shoe!
I find that barrel jeans are often cut slightly shorter, but I find that an ideal place for them to hit is at the ankle bone. However, unlike many other jeans, if these are slightly short, I think they still look great and intentional. So, if you are someone who likes cropped.. you can totally crop these and they will have the same effect!
Pair with….
Slim sneaker: If they are a little shorter (at the ankle or even above) and you can see a sliver of the ankle, they would be great with a taller sock and a sneaker… the key is to pull the sock up UNDER the pant hem so there isn’t a sliver of skim showing. I find that gives a more streamlined look.
Sleek fitted boot: I feel like you want something fitted on the leg and tall enough to go under the hem of the pant. This will prevent the annoyance of the pant hitting the top of the boot and helps to give a clean look. With a baggier pant, I really like something with a longer toe box or something pointy to give some contrast. You can also do a chunky lug boot if you want a more casual look— I just prefer a lug boot that is tighter on the leg as opposed to something that has a wider shaft.
Mary Jane: These are always great with a barrel because they add a sweetness to the utilitarian style and show a bit of the top of the foot. This is nice and prevents it from looking too heavy at the bottom!
Ballet flat: This is sort of similar to the Mary Jane, however, I find with flat shoes and barrel jeans, you want them to be slightly longer. So with a ballet flat, make sure the pant hem hits at the ankle bone or the top of the foot. This will give a more relaxed look and make it feel more modern.
Sleek loafer: Also great if you see the top of the foot… it will give a little breathing room.
Styling & Fit
I made “wide leg” a different section than “baggy” because I think wide legs are more fitted in the leg and wider at the bottom, while baggy are baggy all the way down and are meant to be worn a little slouchier!
If you like the idea of something baggy but want to DIP A TOE, I suggest a wide leg. They are usually more fitted in the waist and hips, so they feel easier to style if you are used to slimmer jeans.
I would categorize these as a hybrid between a flare and a baggy… they aren’t quite as dramatic of a contrast between the fit above the knee and below as a flare, but they have more contrast than a baggy.
I find the best place for these to hit is at the TOP OF YOUR FOOT. So when you are wearing a shoe, it is great for them to be resting on the top of the foot. You don’t want to step on them in the back, but they should cover the back of the heel. If you want to wear these with a heeled boot AND a flat, and want to get them hemmed for both, bring both shoes into the tailor. In my opinion, it is better if they are SLIGHTLY longer with the flat shoes than too short with the boots. As long as you are not stepping on the back, it is nice if they even almost graze the floor with a flat.
Pair with….
Sharp boot: These work with nearly every pant in my opinion. Having the pointed toe or longer toe box is excellent as it really elongates the shape (as opposed to a really rounded toe ankle boot). I also like that it isn’t a heel but still feels sleek and elevated!
Ballet flat/Mary Jane: You want to show the top of the foot here… even if you add a sock, it is nice to just have a little contrast.
Pointed toe heel/flat: Similar to the sharp boot— it is nice to add a little sharpness at the bottom to contrast the wide fit. Seeing a little point peeking out of the bottom also elevates the more casual silhouette and adds polish. And as I said up top, if you bring them to the tailor to wear with heels AND flats— go slightly longer as opposed to too short. I find that wide jeans are really nice when they hit the top of the foot when you are wearing shoes so use that as your guide. The photos above should give good context!
Styling & Fit
A baggy jean is baggy all the way down. This is more of an advanced level… if you are someone who is typically into straight or slim jeans, this would be a huge jump (so maybe try the WIDE LEG first!) These are meant to be worn a little lower on the hips, and I always like when the rise looks kind of long and slouchy. These look great when they are almost grazing the floor. They are meant to even have a little break at the bottom when you are wearing with flats.
Pair with….
Sharp boot: More than any other, the baggy jean is best with something that has a longer toe box or a point. If you wear anything too rounded and chunky, it can look a bit heavy at the bottom (almost like there is a traffic jam between the pants and the shoe). You want the boot to almost act as a “fitted” element, tighter on the foot and a little sleek and sharp to contrast the slouch.
Pointed flat/heel: I love a wide jean with a sleek flat. Just a note that the toe does not need to be super pointy— you can go for something that is more square as well. I personally like these Le Monde Beryl Luna flats because while the toe isn’t super pointy at all, the cut out where the toe is a little longer so it shows more of the foot. MADEWELL also has a great pair that has the same effect! It isn’t quite toe cleavage but the cut out just feels lighter at the bottom.
Rounded flat: They also work with a rounded flat, but you want to show the top of the foot again. I think it can look amazing if it is really slouchy at the bottom and covers the shoe, but I find that to be more of an “advanced” level.
Sneaker: This will have a more slouchy look, but it absolutely works. If you want to give a little polish, maybe try with a jacket that has a sharper shoulder to give a little angle to the look.
Casual mule: Similar to the sneaker, If you really want to lean into the casualness— a mule could be really nice and give that sort of “The Row” relaxed look!
Styling & Fit
To me, these are the easiest and most universally “flattering” jeans. If you have wider hips, a flare or bootcut is excellent because the flare at the bottom is the perfect way to balance the hips. I find often people who have hips will feel like they need to go slim in order to show the bottom of their legs, but the proportion of the flare is actually the way to go!!
I also think that a flare never feels quite dated. It is so '70s that it’s pretty timeless, and brands always have some version of a flare or a bootcut in their assortment. The modernness comes from how you style them!!
Pair with….
Any boot: While I still love something pointed, this is a place where you can go a little rounder or even square if you really want!!
Sneaker: I love the look of a flare with a sneaker. I like when it falls over it and shows the sole of the shoe. It feels really ’70s and retro but still modern and cool for the weekends.
Styling & Fit
Straight leg jeans are great, and to me, these actually have the largest range as they are really dependent on your shape. Some jeans that appear straight can be more fitted, so there is a lot of trial and error here. I think if you want a true straight and feel like they usually look more slim on you, go for something that actually looks a little wider on the model.
I think you can go a variety of directions with the length— as usual, I typically like the pant to hit at the ankle bone, but you can go slightly more cropped (at the ankle) if that is what you prefer!!
Pair with….
High boot: I like the look of a high boot with a straight leg jean— you want a boot with a wider shaft and there might be a little slouch and extra fabric to tuck but I think thats what makes it feel modern and fresh.
Sleek boot: we know by know that a sleek boot works with everything. For this, it is important that the boot is fitted on the leg so that the shaft of the boot fits under the straight leg jean!!!
Chunky boot: I think a chunky boot is also excellent with a straight leg. I think you want the jeans to hit at the top of your foot (when you are wearing the boot) or higher. I think this prevents it from being too heavy on the bottom!
Sneaker: a sleek sneaker feels really nice and polished but still casual. If your jeans hit at your ankle bone or shorter, you can also add a sock. You want the sock to disappear into the jeans so there isn’t a patch of skin showing between the hem and the boot.
Loafer: I think this is the same as the above. I also like a loafer with a straight leg jean that is a little cropped. When you can see a little touch of the top of the foot (and even some ankle!) there feels like there is room to breathe at the bottom.
Ballet Flat: with a ballet flat and straight leg jean it looks nice with the straight leg jeans are a little longer. A cropped slim jean with a flat feels like how we used to wear the ballet flats so I think the longer inseam makes the look feel more modern!
Styling & Fit
I know we have heard a lot about editing skinny jeans, but I think it is more about how you style them. I also think that if you like skinny jeans but want to change them up, you can go for something that is slim through the leg and just make sure it is not SUPER tight on the ankle. The difference between a slim and a skinny is really just that a skinny jean is tight around the ankle.
If you want to feel a little more modern in these, go for a longer inseam. I think what can make the skinny / slim feel dated is if they are really cropped above the ankle. That also makes finding a great shoe to style with them harder! So, if you want the slim look but want to feel modern, go for a longer inseam.
Pair with….
High boot: You can totally do the boot over slim jean here. I think the key is doing a boot that isn’t also tight on the leg. So go for a cowboy, a Moto, or something that gives a little space between the leg and the boot.
Ankle boot: If you want to do a slim jean and ankle boot.. make sure the inseam is long so the jean can fall OVER the boot. It feels a little dated to have the slim jean hitting above or inside an ankle boot. This means that this look requires an ankle boot that is fitted on the leg so it can fit UNDER the hem of the jean.. not over.
Flat: A lot of options here for flats. Again, I like when the hem is a little longer and not cropped, so it feels more modern!
Loafer: I think the key to loafers and skinny/slim jeans is not to go too exaggerated with the contrast. So, you don’t want to have a super slim jean with a really chunky loafer— that will feel a little heavy and really exaggerate the chunk of the loafer. Instead, I like a classic loafer with a sock (or not). Similar to the flats, you want to go a little longer on the hem here. I like when it bunches a little, but if that feels too daring, just have the bottom of the jeans hit around the top of the ankle bone!
Sneaker: You can also do a sneaker. I think a taller sock is great here too… Try styling the sock so that it goes up into the pant leg to create an uninterrupted line. This gives it a sleekness.
While I think every jean category applies to all heights and shapes, I know that jeans can be tough, so I wanted to give a few specifics!
BEST JEANS FOR PETITES
AYR (the short inseam!)
MADEWELL PETITE
PISTOLA
FAVORITE DAUGHTER “Shortie”
J.CREW PETITE
LEVIS (28” inseam)
EVERLANE (27” inseam)
BEST JEANS FOR TALL
FAVORITE DAUGHTER
MADEWELL TALL
JEANERICA (they have 34” inseam options!)
TOTEME (they have 34” inseam options!)
ABERCROMBIE TALL
KHAITE
REFORMATION LONG
So I know you might be asking: what do we wear with these jeans and shoes this fall?! I solved that for you with the chicest knits and jackets (and a tote I couldn’t resist including) from QUINCE!
1. 100% Leather Shearling Trim Aviator Jacket
2. Men's Mongolian Cashmere Crewneck Sweater
I like to get men’s cashmere sweaters instead of women’s— the mens are normally cut with a little more room in the body so if you like a more relaxed look, men’s is the way to go (I usually get one size smaller than I would get in women’s). I also love a grey cashmere sweater. It is sort of like the white tee of the fall… more on that HERE
3. Italian Wool Double-Breasted Slouch Coat
4. Mongolian Cashmere Mock Neck Sweater Vest
A sweater vest is also a great sleek underpinning or you can throw it on OVER a white tee or black turtleneck to add a little texture!
5. Italian Suede Shopper Tote
Thanks so much for subscribing!! Can’t wait to see what pairings you make with your denim and shoes this fall! Happy styling! xx
Lots of great tips here! I’m petite and BSides relaxed lasso fit me really well and hit right at my ankle (barrel leg). Citizens of Humanity Ayla cropped also hit at my ankle and I like the fit a lot (wide leg). I find the Nili Lotan Shon are okay but the knee crease hits a bit low if you’re petite.
Another petite line to check out is Nelle Atelier. it is fantastic. Thanks for answering the eternally tough question of jeans + shoe pairing.