Jeans·9 min read

Our Favorite Denim and Shoes To Pair Together

best-jeans-header
Design: theSkimm | Photos: Abercrombie & Fitch, Quince, Free People, Gap
September 11, 2026

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If you’ve made it to this list, we can assume you’re interested in a new pair of jeans, shoes, or both — or you just love shopping (welcome, friend). No matter your reason, we guarantee there’s something for you here, not limited to but including your perfect pair of jeans. Go forth and find them.

For more affordable, stylish outfit ideas, click here.

taper-jeans

Gap

Mid Rise Straight Taper Jeans

A pair of mid-rise jeans with a tapered leg…

Gap denim is having a moment, and we’re here for it. These jeans have a just-right mid-rise waist, a tapered straight leg that’s not too skinny, and are made of non-stretch denim that only gets better with each wear. 

boots

DV by Dolce Vita

Bindi Boot

A knee-high boot you can stomp around in…

When we think of fall, we think of a really good pair of knee-high boots. These are that pair, from their manageable block heel to the chic pointed toe. You can tuck your jeans into them or wear them with a sweater dress. Plus, Dolce Vita has never once let us down in the comfort department.

j-jill

J.Jill

Authentic Fit Slim-Leg Jeans

Slim-leg jeans with some stretch…

These jeans are made of soft, stretchy cotton denim, so even though the leg is slimmer, you won’t feel restricted in any way. They’re comfortable enough to wear at the airport and come in regular, petite, and tall lengths. 

ballet-flats

Quince

Italian Leather Handwoven Square Toe Ballet Flat

A pair of buttery-soft ballet flats…

Ballet flats are still going strong, especially unique pairs like this square-toe, handwoven version. The leather is so soft that it won’t require breaking in, and they have extra insole padding (which makes them great for commuting). We love the Merlot ones. 

low-rise-jeans

Abercrombie & Fitch

Curve Love Low Rise Ultra Loose Jean

A loose pair for cool girl vibes…

Abercrombie really outdid themselves with this pair. They have the same low-rise fit as their classic low-rise jeans, but with a wider, extra-loose leg. We feel so cool when we wear these with sneakers and a cute top, so now we’re eyeing a new wash. 

pumas

Puma

Speedcat Ballet Sneakers

A ballet flat-sneaker combo…

Ballet sneakers are here to stay. This one has the same comfortable insole as our beloved Speedcat sneakers and elastic bands to keep your foot in place. Wear them with frilly socks and a skirt, why not?

flare-jeans

Old Navy

High-Waisted Wow Flare Jeans

A pair of flared jeans that look more expensive than they are…

These jeans are high-waisted, have a good amount of stretch, and have a flared leg that’s not too ‘70s. They pair well with jeans or heels, and the denim looks better than half the pricier pairs in our closet. 

loafer

Quince

Italian Suede Penny Loafer

A suede loafer that comes in fun colors…

We’re seeing suede loafers everywhere. These are great for casual and office days with their classic penny loafer style and cushioned insoles. Grab the powder pink and one of the neutral colors. 

levis

Levi's

Ribcage Straight Ankle Women's Jeans

A pair of Levi’s that look vintage…

You could wait your entire life to find a perfect pair of vintage Levi’s — or you could buy these. They’re the highest rise the brand makes, which means you can wear a cropped top without fear of showing anything, and the denim has just a hint of stretch. The ankle length means they’re great for showing off your shoes.

new-balance

New Balance

574 Sneakers

A new version of the New Balance 574s…

One editor is a New Balance 574 devotee, so when she saw the leopard version, she had to grab them for fall. They’re the same reliable, extremely comfortable sneaker, but with a textured leopard print. They’ll turn your jeans-and-a-tee outfit into something exciting. 

frame

Frame

The Gray

Our current denim addiction…

People have been talking about these jeans, so we had to give them a try. Trust us, they live up to the hype. They’re low-rise, but in a comfortable way, with a wide flared leg that elongates your legs like crazy. Plus, they come in a petite length, so you won’t have to hem them. 

90s-jean

Abercrombie & Fitch

High Rise 90s Relaxed Jean

A pair of ’90s-inspired jeans you’ll come back to every year…

These are not the Abercrombie jeans of your youth. This silhouette has been perfected to emulate your favorite ’90s sitcom icons (we’re looking at you, Rachel Green). They’re fitted in the butt with a relaxed leg that wears well with boots or heels. 

lee

Lee

Women's Premium LQD High Rise Retro A-Line Jean

A high-waisted pair you’ll reach for day after day…

These have a retro fit but are made of soft, comfortable denim that moves with you. You’ll find yourself pulling them on to run errands or for a casual hang, rather than just when you want to dress up. The Lee back pockets are iconic. 

vagabond

Vagabond

Elvina Ankle Boots

A pair of ankle boots that stand out from the crowd…

These are not your typical ankle boots. They have three side buckles that give them a bit of edge and a square-toe that looks chic popping out of your jeans. They’re an investment, but Vagabond shoes are always comfortable and last for years. If you can’t wait for them to be released, this version without the buckles is just as good.

bootcut-jeans

Madewell

Relaxed Bootcut Jeans

A bootcut pair that comes with or without stretch…

If you’re looking for a relaxed pair of boot-cut jeans that don’t lean too cowboy, these are the ones for you. Pick either the non-stretch denim with tasteful distressing at the knees or the light wash pair with a little stretch. You can’t go wrong with either pair. 

birkenstocks

Birkenstock

Boston Rivets Clogs

The original Boston Birkenstock with a fun touch…

When we bought these on a whim, we had no idea how essential they would be to our fall and winter wardrobes. Not only do we wear these supremely comfy clogs on a coffee run, to a Pilates class, or to the grocery store, but they also look surprisingly polished with jeans or trousers to the office. The rivets give them an elevated look. 

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