Shoes to Wear with Skinny Jeans

When it comes to styling skinny jeans (stick around to read why they’re here to stay), the most common question or concern is what shoes to wear with skinny jeans. In my years of experience, I think just about every shoe goes with skinny jeans – it’s a little matter of length, cuffs, and style.

I’ve heard talk recently that skinny jeans are no longer in style. Well! I’m here to say that I don’t care what’s “in,” skinny jeans fit my body type and my style, so they’re sticking around, round here. They’re almost all I wear. No, seriously. Except for an occasional boyfriend jean and my somewhat middle of the road summer jeans, I’m in skinny jeans – of all colors!

Shoes to Wear with Skinny Jeans

Besides skinny jeans fitting my style, I just find them so unbelievably versatile. Last spring, my Ireland packing list included just two pairs of skinny jeans – no other pants for 10 days! The real trick there is learning what to wear with black jeans as they’re the quintessential day to night bottoms.

But as you can see here, I don’t just stick to black jeans…

Skinny Jeans with Flats

I think the easiest shoes to wear with skinny jeans are flats or loafers. It’s very Audrey Hepburn-esque and that’s always a win (see how to wear a beret for that full AH vibe). This combo is very adaptable, however, from a basic sleeveless top to a winter sweater and jeans like in this Ron White shoes outfit.

Flats also can easily tone down a blazer and jean combo for one of my favorite fall winery outfit go-tos.

Skinny jeans with tennis shoes

I’m also big of tennis shoes to wear with skinny jeans. One of my biggest tricks here as you can see above is cuffing my jeans to show a little ankle. I love this trick especially when traveling – wearing black jeans with walking shoes for touristy things and then swapping out for nicer shoes for dinner. See my fall weekend packing list and this dark washed jeans outfit for inspo.

With high top sneakers, I let the weather decide whether I cuff my skinnies or not. Like in the cold winter, there’s no ankle showing! See What to wear in 40º weather and a few navy shirt outfit ideas for more outfit details.

Boots to Wear with Skinny Jeans

Besides knee-high boots, I found lower boots the most challenging shoes to wear with skinny jeans, but now I’ve leaned into it, partly getting over it, and partly via the cuffing approach!

I wear my beloved brown boots with black jeans a lot – through fall and winter. In fact you can see the combo from years past in my layered sweater outfit.

Though not heeled, it was also easy with flat, knee-high boots. I adore this whole turtleneck with leather jacket layering situation.

I have “regular” height boots (i.e. not knee-high or ankle-low) with a medium heel. I alternate between cuffing my denim and pulling them gently over the top of the boot. See them in my fall family photoshoot outfit and in my post on how to style a sweatshirt!

This knit sweater outfit shows skinny jeans with wedge ankle boots and my casual mom outfit with a vest and a sling bag shows skinny jeans with my beloved Chelsea boots – a short, flat boot.

How to Wear Skinny Jeans with Heels

Besides sandals, below, skinny jeans and heels is probably the most straight forward. Heels and skinny jeans both elongates legs (which my shorter legs appreciate immensely). You can see my favorite sustainable heels brand and get my Sarah Flint discount code here for fabulously made shoes!!

Sandals & Skinnies

This one is really a no brainer and if you ever wonder what I’m wearing, it’s probably some version of sandals and skinny jeans about April/May to November!