Photo by Alex Shalamov/iStock
This is one of the biggest challenges we all face. So today I’m going to address the question of which shoes work for different hem lengths of pants, jeans, dresses and skirts. Keep in mind that fashions trends and hem lengths are constantly changing. Also, the “rules” for which shoes to wear with different clothing are in flux. But there are some general guidelines for balance and proportion that are pretty consistent.
Bottom to top?
Let me start with a very practical approach. It’s one that some smart women consider, especially when packing for travel. That is, start from the bottom up. Figure out which shoes you want or need to wear that day or for a particular event and then build your outfit around them. This makes a lot of sense when the weather mandates what you need wear on your feet.
Fundamentally, it’s still a matter of creating proportional balance – for your own proportions. And, of course, individual style is a factor. So, I’ll also add a few notes about how different shoe details and fabrics reflect the different style archetypes.
We’ll look at eight different shoe styles and the hem lengths that work for each of them.
Sneakers and Trainers
In the beginning of my book, She’s Got Good Jeans, I wrote that jeans have become a universal garment. Similarly, sneakers have become pretty much a universal form of footwear. For Natural style types, this was always the case. But a few years ago we began seeing fashionable women in European capitals, women of all style essences and ages, ditch their heels for the comfort of sneakers. And they wore them with everything: dresses and skirts, pants and jeans, trench coats – you name it.
First were the plain white canvas or leather sneakers. Then came the “cool” versions: Adidas striped leather sneakers, and colorful trainers. Simple mono-colored sneakers, whether leather (which adds more Classic) or canvas (more Youthful or Natural) will not detract from the whole look as much as more flashy or decorated styles will. Here are some examples for each of the fundamental style essences. Then we’ll explore the best hem lengths to wear them with.
I have these “Caren” sneakers (below) in white, yellow (I think that color is only available in the summer) and gray. They are extremely comfortable and they elevate a casual outfit.
Josef Seibel “Caren” sneakers $140
Adidas Court sneakers are the “it” ones right now.
Adidas “Court” Sneakers Amazon $73.77
For Dramatic types metallic textiles are a great option. Yes, everyone is wearing silver shoes now, and they are a cool addition to any outfit. But in terms of textiles, metallics are a bit Dramatic. They can also read as Angelic, although some Angelics have to tread lightly (pun intended) in the sneaker direction.
Donna Karen “Donna” gold sneakers Macy’s $84
But speaking of an Angelic type, here ya go!! 🙂
Im.Mi “Goldie” Rhinestone Sneakers Amazon $98.99
You can get away with wearing them with anything if you have a lot of High Spirited or Natural style. Romantics, might want to look for a pair in one of their range of reds.
Brooks “Adrenaline” GTS sneaker/running shoe Amazon $84.95
As for pant hem lengths, if you are wearing wider legged pants or jeans you will want the hem to fall gently over (at least) the first two crisscrosses of the laces on your sneakers. If you are wearing fitted sweats, leggings, or any pant that has elastic gathers at the ankles the pant hemline should be ankle length or slightly cropped. But keep in mind that look will truncate the look of your legs. Also, calling attention to the demarcation line of the pant and the start of a shoe or sock will draw attention to that area. For legs that are slim or longer that can work. Shorter or chunkier legs will do better with a longer hemmed pant. If you don’t care what other people think, go for it.
Slim or skinny leg jeans and pants should end at the ankle bone or slightly above the tongue of the sneaker. For rolled-up jeans and pants, let your ankle and part of your lower leg show.
Ballet Flats
Rothy’s “The Point” flats (Yellow is only available in the spring and summer)
This is a fundamentally Classic style shoe. But depending on the textile, toe shape, and embellishments, it can also appear Youthful, especially if it has a rounder toe and/or a bow of any kind at the top. If it’s slightly squared at the toe it becomes more Natural. If it’s almond shape it becomes Classic.
Ballet flats are a natural combination with fuller or longer skirts and dresses. A fitted midi length slim skirt, by its nature, is a bit Romantic and Dramatic. A flat will dampen that down. When wearing flats with longer, wide legged or draped pants, the hem should fall or drape across the top of your arch or just very slightly past that point. With straight leg pants and jeans, the hem should be just slightly above your ankle bone. Cropped pants and jeans can end pretty anywhere beneath the widest part of your lower leg but above your ankle bone by a couple of inches.
Cody Ballet flats $70.49 with code: SHOP at Macy’s
Sam Edelman Marilyn Flat $130
Naturalizer Connie Slingback $89.97 Macy’s
If the flat is in a shiny metallic leather or sequined it could be either Dramatic or High Spirited, as those are more costume-y looks. This one is mostly Dramatic because of the point and the textile.
Nine West Lalin silver flat Amazon $66.75
Crystals and sequins can read as slightly Angelic. If the shoe is sheer, such as the popular mesh flats this past summer, they also become Angelic.
Arqa Crystal Embellished Flats Amazon $66.75
Riekhanny sheer flats Amazon $54.99
I wanted to show you a great pair of no-show socks that I wear with flats. These are from Sheec. They are comfortable and fit perfectly. The also come in other sizes to fit sneakers and other shoes.
Animal prints flats are usually Natural or Dramatic, or in some cases High Spirited. But leopard is having a big resurgence this fall and it petty much works for anyone. Just look for a background color that is either warmer or cooler depending on your undertone. Flats in one of those prints could work well for a lower hem skirt or dress. A midi denim skirt would be terrific with these, and a denim blouse combination is very fashion-forward this year. The hemline for a fitted midi looks best if it falls a bit below the widest part of the calf. The leopard flats I’m wearing in the above phot are very from Zara but are no longer available. Here are similar ones.
Vionic Alameda Mary Jane leopard flats at DSW $129.96
C. Paravano leopard slingback $138 on Amazon
When wearing flats with fuller skirts or longer skirts the hem should fall either a bit below the knee, mid calf, or midi length. Because of their visual “weight” maxi skirts and dresses require a heavier shoe.
Old Navy Cozy Ribbed Maxi Skirt $23.99
Slingback flats tend to be a tad more formal.
Anthropologie Guilhermina flats $89.95
Naturalizer Hawaii Sling back $93.51
Mary Janes
Another type of ballet flat is the Mary Jane shoe (like mine from Zara shown previously.) Since their advent in the 1920s and 1930s they periodically have a surge in popularity. Now is one of those times. The strap across the instep adds a Youthful quality. I have only 5% Youthful, but the color and textile of these work for me, especially because my pant length will cover the strap. (I bought them in this rich brown and black.) I’m thinking of getting the silver ones from Marc Fisher too!
Madewell “Greta” Mary Jane flat $98
Marc Fisher Mary Janes Nordstrom Rack $59.97
Amazon Essential Velvet Mary Janes $23.70
Note that any strap over the arch of your foot or for that matter, around your ankle, will truncate the look of your lower leg and of your foot. If you have long feet (like I do) this will make them look more petite.
Boots
The shaft of the boot is the guiding principle on how to pair them with your wardrobe. The narrower the shaft, the more formal the look. The bulkier or wider the shaft, the more casual.
Over-the-knee slim shaft boots will work for almost any length skirt because they simply become de facto leggings. They will also work with miniskirts as long as the the top of the boot ends below the hemline of the skirt or dress, allowing a few inches of leg to be shown. Keep in mind that this is a Dramatic look. If you have zero Drama, it might be one to avoid.
Wider, slouchy or chunky boots are also best worn with slimmer pants and jeans. (Yes, skinny jeans are coming back. It was inevitable after all the wide leg pants and jeans.)
Clark’s Slouchy suede boots $73.98 Walmart
Amazon Essentials Tall Block Heel boots $42.50
New York and Company Rana over-the-knee Boot Macy’s $43.98
Ralph Lauren Artisan Mid Shaft Suede Boots at Macy’s $225
Booties
Jodie Filogomo: J Touch of Style
For those with a lot of High Spirited or Natural style, booties are a no-brainer. You just don’t want the boot top to keep rubbing against the hem of the pant when you walk. We’re seeing a return to rolled up hems on jeans (hello again, 1980’s!) And as long as there is even a tad of space between the hem and the top of the boot you’re good to go. (This is from Jodie Filogomo’s site. She was one of the guests on my Expert Edition series and she has a very high percentage of High Spirited style.)
For straighter jeans and pants, the hemline can be at or above above the ankle bone. For slightly flared jeans or pants, the hemline should fall lower – at or slightly below the arch of the foot.
Lee’s Jeans on Amazon $22.90
Lee’s Shaping Bootcut Jeans on Amazon $22.94
Democracy Ankle Simmer jeans on Amazon: $64.65
Banana Republic Suede Ankle Boots $105 (plus 20% off at checkout)
GAP Ankle Booties $54.97 or $24.97 (Also in gray)
A new-ish combination is the kitten heel on a boot or bootie like the GAP ones above. Frankly, when they first came out last year I thought they looked really silly as that heel reads as delicate and yin. Boots and booties are typically more yang. I still think the taller shaft kitten heeled boots aren’t going to have a long shelf life. But I saw these black faux suede booties on a huge sale on GAP and bought them. I wore them in the winter with jeans and they looked kind of cool (and were surprisingly – almost shockingly – comfortable.) Will they be something I’ll pull out every year forever? Somehow I don’t think so.
Regardless of heel shape, booties and higher shaft boots pair well with midi skirts and dresses.
Michael Kors pleated snake print skirt at MAcy’s $175
Booties can be paired with shorter skirts including minis. They add balance and ground the overall look. This look from Anthropologie (above) demonstrates the look. It is especially effective because the booties are in a lighter shade. Darker colors would be a little heavy for this look.
Volatile Brand Bronco Booties $78.29 on Zappos
Pumps and Heels
Heels at any height are always going to be dressier than flats unless the flat is highly embellished (with things like rhinestones or a large bow or is in a textile like satin or patent leather and meant to be worn with more formal attire or a tuxedo-type satin outfit.)
Again, the pointier the toe, the more Dramatic the look. The higher the heel, the more Dramatic the look. My opinion is that stilettos look best when worn with knee length or sightly below the knee skirt lengths.
As for dresses and skirts, minis with higher heels are a luxury reserved for the young. (I know I’ll get a lot of flack for that from older women with great legs…if that’s you, carry on!) It’s a cute date-night/club look, especially for High Spirited types and some Dramatic ones. With longer skirts or dresses higher heels read as both Romantic and Classic.
For wide leg pants both the width of the pant and the height of the heels also take the look toward drama. The hem can be anywhere from just above the top of your arch to considerably below. That slouchy, dragging-on-the-ground look is more Dramatic than the slouchiness we might associate with a more Natural look. And of course, stilettos with jeans is a more Dramatic look in general. Long slouchy hemmed pants with flats, sneakers or slip-ons is the more Natural version.
Kenneth Cole Riley Pumps at Nordstrom $99.99
Calvin Klein Gayle Pumps at Macy’s $109
Naturalizer Karina Pumps at Macy’s $109.95
For rolled cuff pants, a low heel adds a bit of yin to a very casual outfit. The hem should come a bit above the ankle bone. Slouchier denim and rolled cuff pants are Natural, but wearing them with a lower sling back heel adds some Classic, and possibly Romantic.
Tayla Cole Haan Slingback kitten heel at Nordstrom $168
Sam Edelman Bianka leopard sling back heels $160
Banana Republic Factory Vegan sling back kitten heel $60 (plus 20% off at checkout)
BTW – If you’re not wearing tights or stockings with your pumps I love the no-shows from Sheec. They also have half foot covers for wearing with slingbacks.
Loafers and Slip-Ons
Whether you wear loafers, deck shoes or slip-ons the hemline for the pant jeans shouldn’t be any lower than the top of your ankle bone. In fact, showing a bit of ankle is a nice way to wear these types of shoes. (These are the Sheec no-shows for sneakers and loafers.) 
When wearing penny loafers or tasseled loafers, the slot for the penny or the tassel should show above the pant hemline if you’re wearing a longer and wider-leg pant. You just don’t want the hem to fight against the tassel or other feature. Loafers will ground any look and take it either Classic or Natural. They work with minis in more Natural textiles, like denim. Loafers with box pleated skirts are a preppy look. You can even wear them with satin midi skirts (as shown in the Quince skirt above.) But if you’re wearing them with such a more obviously feminine skirt, they work best when they color of the shoe is similar to the skirt.
Quince washable silk slip skirt $59.90
Quince suede penny loafers 79.90
Vionic loafers on Amazon $70-$135 (based on color)
Earth Javas on DSW $108.99
I hope this gives you enough visual information to make decisions when faced with this ongoing dilemma about hemlines and shoes. Write me to let me know if this was helpful: andrea@shoppingfortherealyou.com
Drawing by Sue Tait Porcaro
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