Wondering What Shoes to Wear with Skinny Jeans? Try These 9 Trendy Styles

We’re very excited about the return of the ballet flat, but this particular jean/shoe combo threatens to leave us looking like a cast member from The Hills. There are few styling tricks to keep in mind that will keep your look firmly in 2020. First, opt for darker washes over lighter blues. Second, find a pair of jeans that hits somewhere between your ankle bone and the top of your foot—and no scrunched fabric, please. Finally, consider a trendy raw hem and pointy- or square-toe flats over rounded styles.

Shop ballet flats: Soludos ($98); Sam Edelman ($120); Linea Paolo ($140); Vince ($275; $165); Mansur Gavriel ($375)

Chunky loafers are another hot 2020 footwear trend and they happen to work seamlessly with skinnies. In this case, we suggest showing off a bit more ankle, so you could even try a cropped fit. The goal here is to uphold the balance between curve-hugging denim, bare skin and the hefty soles of your shoes. Showing a bit more ankle helps maintain the shape of your legs without burying them in a super-long hem or cropping your calf at an odd place.

Shop loafers: Louise et Cie ($140; $84); Sarto by Franco Sarto ($150; $90); Everlane ($156; $94); Tory Burch ($328); Frame ($428)

Following the precedent set by flats and loafers, sneakers look best when paired with a shorter inseam (which may require rolling, hemming or chopping, if you’re petite). While low-profile sneakers like Keds, Converse or Vans look great with the super tight fit of jeggings, we suggest going a bit looser for chunkier or taller kicks. That’s because sticking a shoe with an exaggerated sole at the end of the long, lean line created by your skinnies can make your feet look large or even clownish. While you don’t need to swap in straight-leg or boyfriend jeans, just pick some denim that isn’t skin-tight.

Shop sneakers: Keds ($75); Cariuma ($79); Ecco ($160; $100); Greats ($179); M.Gemi ($198); Koio ($248)

Sure, you could always tuck the ends of your pants into your boots, but we love Coterie member Grace Atwood’s fresh trick of choosing jeans and booties that begin and end at the exact same point. Unless you’re willing to take your jeans to be hemmed or snipping them at just the right point, this styling method will involve a bit of trial and error with the pieces in your wardrobe, to find just the right pairing. (Don’t fret if there’s a little bit of overlap or a sliver of skin between the two; getting close is all that matters.)

Shop ankle boots: Chinese Laundry ($100); Franco Sarto ($119); Marc Fisher Ltd. ($190); Everlane ($236); Dear Frances ($575)

For lace-up styles like combat, hiking or moto boots, try tucking your jeans into both your shoes and your socks. In fact, you could even allow your sock to poke out just a little bit over the top of your boot. These styles tend to come with a strong ’90s grunge vibe, which you can either lean into with a modern shacket or veer away from with a luxe-looking camel cashmere cardigan.

Shop combat boots: Dr. Scholl’s ($80); Crown Vintage ($80); Schutz ($158); Dr. Martens ($180); Rag & Bone ($525)

When it comes to comfy sock boots, wear yours with jeans that skew a little looser at the ankles. That way, they can easily slip over the top of your boot. As for your top half, a chunky turtleneck or oversize blazer is a great way to balance all the clingy fabrics on your lower half.

Shop sock boots: Steve Madden ($100); Jeffrey Campbell ($125); Vagabond ($160); Botkier ($168); Stuart Weitzman ($575; $432)

Baggy knees and awkwardly stuffed boot shafts are neither flattering nor stylish. Footwear that hits anywhere above the middle of your shin requires the slimmest-fitting denim you’ve got—yes, even if your boots are wide or slouchy on their own (two popular silhouettes for fall 2020). For styles that hit at or below the knee, it’s most flattering to choose a dark wash, like a black or gray, especially if you’re also wearing black boots.

Shop mid-calf and knee-high boots: Bleeker & Bond ($150; $75); Naturalizer ($230; $110); Paige ($598; $240); Tory Burch ($548); Loeffler Randall ($695)

Now’s the time to reach for those skin-tight jeggings once again, to prevent bagging or bumps along the shaft of your boot. Pro tip: Tuck your jeans into your socks as well to make pulling on these mile-long boots easier and to ensure your pants won't suddenly find themselves bunching as you go about your day. As for your top, opt for a sweater or a blouse that hits right at the hip to maintain your body’s proportions.

Shop over-the-knee boots: Lulus ($55); Steve Madden ($130); Thursday Boot Co. ($235); Marc Fisher Ltd. ($350); Stuart Weitzman ($400)

Animal prints—from leopard to snake and even zebra—are having a major moment right now for accessories of all kinds, including tall boots. Generally speaking, these multi-colored options look best with either dark-wash or neutral-hued denim. If you’re working with shoes that are generally light in color, like Coterie member Ijeoma Kola’s snakeskin boots, pair them with white, cream or light-gray washes. If you’ve got a print that incorporates more blacks or dark browns, try a pair of dark skinny jeans in a coordinating color.

Shop animal print boots: Dolce Vita ($252; $89); INC International Concepts ($150); Vince Camuto ($150); Schutz ($238); Tony Bianco ($372); Paris Texas ($780)