We’re currently in the midst of Nordstrom Anniversary Sale shopping, and one of my favorite sale finds were these Levi’s 501 jeans. They’re a less-distressed version of the 501s I’ve been living in for the last several months…and I think they’ll be a better choice when the weather cools. 

Initially, I found Levi’s 501s a bit tricky to wear. They’re equal parts mom jean and boyfriend jean, and neither of those denim styles are foolproof when it comes to footwear. So here are the shoes that are currently working for me, as well the boots I think will help transition these jeans into cooler weather.

NOTE: Since I’m still narrowing down (theoretically) my #NSale haul…I used many of the pieces here to help illustrate the looks. Almost everything, therefore, is on sale. And YES: I can. not. decide between the two Clare V bags. WHICH ONE???

The 10 Best Shoes & Boots To Wear With Levi’s 501 Jeans

Most foolproof shoes: Mules
Most foolproof sneakers: Classic Vans
Shoes to dig out of your closet: Ballet Flats
Most walkable shoes: White fashion sneaker (p448, Golden Goose, Adidas)
Best shoes to dress Levi’s up (summer): nude heels (match skin tone)
Best shoes to dress Levi’s up (fall): pointy black heels
Best boots to dress Levi’s up (winter): sleek, high-shaft sock boots
Most foolproof boots: Heeled Taupe Ankle Booties
Best everyday boots (besides taupe): High Shaft booties (in army green, tan, gray)
Best boots for snow or muck: Military lace-up boots (like Doc Martens)

1. Most Foolproof Shoe To Wear With Levi’s 501: Mules

Mules are like the high-heels of flats: they always look good. The downside, of course, is that they’re not that walkable (at least over long distances). In any case, this is an outfit I’d wear to walk down the street for socially-distanced drinks with a neighbor, or wear to a backyard bbq.

Top – xs | Levi’s 501s – 27 (I sized up 2 sizes) | Levi’s 501s (not in the sale) | Bag | Mules

2. Most Foolproof Sneaker To Wear With Levi’s 501: Classic Vans

I do not know why classic Vans work so well with basically every outfit — including Levi’s 501s — but I’ll take it. Vans are classic for a reason.

Top – xs | Levi’s 501s – 27 (size up) | Levi’s 501s (not in the sale) | Bag | Vans | Mug (from one of my fav black-owned businesses!)

Or Warm It Up With a Fleece…

Top | Fleece | Levi’s 501s | Levi’s 501s (not in the sale) | Bag | Vans

3. Shoes To Dig Out Of Your Closet: Ballet Flats

These were a pleasant surprise! I think the reason these work so well is because ballet flats are so inherently feminine…and Levi’s 501s are the ultimate tomboy jean. The combo is perfect. 

Top – xs | Levi’s 501s – 27 | Levi’s 501s (not in the sale) | Flats | Bag (left) | Bag (right)

And Warm it up With a Fleece…

Top – xs | Fleece – s | Levi’s 501s – 27 | Levi’s 501s (not in the sale) | Flats | Bag

4. Most Walkable Shoe To Wear With Levi’s 501: White Fashion Sneakers

Frankly, if I couldn’t make sneakers work with 501s, I never would’ve worn the jeans. The key for me has been to make sure the jean is cropped enough, otherwise the result is…squatty (is that a word?). ANYWAY. I cut the hem of my 501s off to work with ankle boots, and then — for sneakers — folded the hem up once to create a cuff. You can either smooth the cuff out with your hands and give it some time (it’ll eventually stay) or just iron it.

Top – xs | Levi’s 501s – 27 | Levi’s 501s (not in the sale) | Sneakers | Tote

NOTE: One reason these p448 sneaks look so cute is because they have a slight platform.  This pair is almost sold out, but these Steve Maddens also have a similar platform, which may make them especially flattering.

Warm It Up With a Coat….

Top – xs | Faux Fur Coat – xs | Levi’s 501s – 27 | Levi’s 501s (not in the sale) | Sneakers | Bag

I love how the vibe of this outfit changes drastically with a different coat. I also love that even the longer coats look good with the 501s and sneakers.  

Base Outfit: Top – xs | Levi’s 501s – 27 | Levi’s 501s (not in the sale) | Sneakers

Coats: Puffer (top) – xs | Trench (bottom) – s

Bags: Crossbody (left) | Tote (right)

5. Best Shoes To Dress Up Levi’s 501s In Summer: Nude Heels

There’s a lot going on with 501s — they’re faded, sometimes distressed, with a high-rise and baggy legs…so I like to keep it simple with a nude heel. Just find a shade that elongates your leg — it doesn’t have to match your skin exactly. (And I’m always looking for a heel that’s walkable and comfortable, too.)

Sweater – s | Levi’s 501s – 27 | Levi’s 501s (not in the sale) | Sandals | Bag

6. Best Shoes To Dress Up Levi’s 501s In Fall: Pointy Black Heels

Again, since these jeans have such a relaxed vibe, one easy way to dress them up is to pair them with a really sharp black heel. I don’t really do stilettos, but a pointy-toe and sexy cut-out does the trick, too.

Sweater – s | Levi’s 501s – 27 | Levi’s 501s (not in the sale) | D’Orsay Pumps | Bag

7. Best Boots To Dress Up Levi’s 501s In Winter: Sleek, High-Shaft Sock Booties

Sock boots slip right under the hem of the jeans…and stay there. It’s the sleekest possible look (and warm, too, especially if you wear black Smartwool socks underneath). The sleek silhouette helps to offset the casual denim, and the darker color is balanced by wintery textures on top (wool, sweaters, etc).

Left Coat – s | Right Coat – xs| Levi’s 501s – 27 | Levi’s 501s (not in the sale) | Boots | Bag

8. Most Foolproof Boots To Wear With Levi’s 501: Taupe or Tan Ankle Boots

Since most Levi’s 501 jeans have that faded, perfectly-broken-in wash, taupe ankle boots are an easy win. Since the boot color is lighter (AND the denim color is lighter), the combo serves to elongate the leg line. I wrote an entire dissertation I mean article (ha!) on the topic, here.

Top – xs | Levi 501s (not in the sale) | Bag | Booties

NOTE: The Marc Fisher boots above are comfortable, but they have too high of a heel. I’m still looking for my perfect taupe boot for winter.

The Idea Is To Not Contrast With Your Skin

If your ankle boot has a high shaft and your skin doesn’t show…then taupe is my top choice. But if your ankle boot is low and skin does show….the idea is to find a taupe (or tan or brown) that isn’t a huge contrast with your skin tone. Even a really dark brown boot will read ‘less heavy’ than black boots.

Sweater – s | Levi’s 501s – 27 | Levi’s 501s (not in the sale) | Booties (Vince! on sale at Nordstrom Rack)

9. Best Everyday Boots (Besides Taupe): High-Shaft Boots in Army Green, Tan or Gray

Again, because Levi’s 501s tend to be faded…almost any color of boot that’s not black will have less contrast, a longer leg line and better balance. (The one exception to this rule is red or maroon: they’re so strong that they’ll read more like black.) 

Sweater – xs | Levi’s 501s – 27 | Levi’s 501s (not in the sale) | Longchamp Tote | Boots

These Vince boots are insanely comfortable to walk in — they don’t feel nearly as high as they look. I just ordered the ‘sand’ color which, admittedly, looks pretty awful online. I’m hoping that the sand is much cuter in person but if not…I’ll keep the green.

Warm It Up With A Coat

Moto Jacket  – xs | Levi 501s (not in the sale) | Bag | Boots

NOTE: These are my original 501s…and I still think I like this wash better? Admittedly, I won’t be able to wear them once it gets cold outside, but they’ve been pretty perfect for summer. 

With Oversized or Tucked Sweaters…

Since I’m trying to get ready for Fall, I decided to play around with some possible outfit formulas. Here are two that seem easy enough for the rest of 2020 (yet still look cute).

Left Sweater – xs | Right Sweater – s | Levi’s 501s – 27 | Levi’s 501s (not in the sale) | Bag | Boots

10. Best Boots For Snow or Muck: Military Boots (like Doc Martens)

I’ve yet to figure out a true snow boot option for Levi’s 501s (or heck — I’ve yet to find a true snow boot option for mom jeans or boyfriend jeans in general)…so if you have, please share! Instead, I’m going to rely on my trusty Docs, worn with thick wool socks, to get me through cold, wet days.

Moto Jacket – xs | Sweater – s | Levi’s 501s – 27 | Levi’s 501s (not in the sale) | Bag | Doc Martens (not in the sale)

NOTE: If you are #NSale shopping, I love the look of these Sam Edelman military boots.  The leather (in person) is gorgeous, and they walk that line of not being either too much…or too boring.

One Final Fail….

In our recent article, “Best Boots For Light Wash Jeans? Taupe.,” a reader asked why I only recommended taupe sneaker boots for skinny jeans, NOT for mom jeans/boyfriend jeans/etc.  Here’s a good illustration of why: 

Sweater | Levi’s 501s | Levi’s 501s (not in the sale) | Left Sneaker Boots | Right Booties

You can see how cute taupe sneaker boots look with skinnies, here and here.

xo,

S