My Favorite Chunky Loafers and How to Wear the Trend

Loafers have always been a great staple in any fall wardrobe. You can dress loafers up or down, and they’re a great middle-of-the-road alternative to both sneakers and heels. Want something fancier than a sneaker? Grab loafers. Want to look polished but don’t want to wear heels? Grab loafers. Also, while the loafer itself is here to stay, today’s on-trend versions with chunky soles feel edgy and modern. 

Here are some style tips and outfit ideas on how to style chunky loafers this season. To shop, scroll to the bottom of this post where I’ve rounded up over 25 of the cutest chunky loafers out there.

(My exact black chunky loafers in this post are under $100!)

How to Wear Chunky Loafers

How to Wear Chunky Loafers

Invest in a Neutral

To get the best bang for your buck, purchase a pair of chunky loafers in a classic color such as black, brown, or another neutral. These will work with anything in your closet, regardless of formality, color, or item. I’m personally a fan of black patent loafers because the shine adds some extra personality. I’ve had my black patent loafers for a few years; you can find my exact chunky loafers under $100 here.

Try With Straight Leg Jeans or Pants

So, look for slim, kick flare, or straight jeans or pants that hit at or just above the ankle. Chunky loafers are bulkier, so even out proportions with something in a straight silhouette. Personally, I’d stay clear of skinny jeans for these shoes, because your feet will look clunky with such tight fabric. (If you do want to wear skinny jeans, then offset the chunky loafers with an oversized, boxy coat or blazer.)

Here are few of my favorite jeans to pair with chunky loafers:

Pair with Something Short

Miniskirts, leather shorts, and short dresses are a major yes when it comes to chunky loafer outfits. Make these pieces seasonally appropriate and add hosiery like socks or tights (more on this below). 

Add a Blazer

So, if you’re looking to dress up your chunky loafers, add a blazer. This third piece fashion trick works well with jeans and a tee just as well as it does with a short skirt.

Chunky Loafers with Socks 

One of my favorite ways to wear chunky loafers is with socks. Younger me would have cringed at this thought (“Too preppy!” I’d say), but there’s something I love about the pairing with today’s bulkier shoe silhouette. Something about it feels a little less precious and a little more cool-girl. Also, you can wear white socks, black socks, or even socks in a bright color to add a fun pop to your look.

Add Tights

For cooler days, add tights to your high-hemline chunky loafers outfit. So, you’ll be able to achieve the same leggy look with an added layer of warmth.

Chunky Loafer Outfit Ideas

Mini dress outfit with chunky loafers and socks
A Mini Dress and Socks

You don’t have to just stick with jeans when styling a chunky loafer outfit. Try a fun mini dress and some sheer black ankle socks.

A Trench Coat

A khaki trench coat is a great closet staple. This tan trench coat over the black plaid pans and black top adds a pop to this look while remaining neutral.

White Button Down and Black Leather Shorts with Chunky Loafers

I am all for this black and white outfit. If you don’t have black a black mini skirt, try a black pair of shorts skirt. This white oversized button down shirt with the half tuck makes this feel effortless, but still put together. Sort of an undone tomboy meets school girl vibe.


A Black Turtleneck and Blazer

A black turtleneck is a fall staple for me. This combo is a great work option or if you have an important business meeting. It’s chic meets sleek.

Chunky Loafers with a Midi Skirt

A midi skirt like this plaid one, a black turtleneck, and some chunky loafers is a polished, feminine way to wear the shoe trend. This modest yet fashionable outfit works for the office or classroom.


How to Wear Chunky Loafers with jeans
Chunky Loafers with an Oversized Blazer and Straight Leg Jeans

Blazers are an essential part of a fall jacket collection. Ditch your fitted workwear blazer and opt for a boxier cut that hits bellow the hip to look more current. A white tee keeps this look casual.

This blazer from Sezane is a closet staple for me.

Chunky Loafer Outfit Ideas
Chunky Loafers and a Long Coat

I love the ankle-grazing length of Selena Gomez’s coat, which matches that of her straight leg jeans. Topped with a white tee, this casual look still feels thought out and polished.

Chunky Loafers with Black Socks
Chunky Loafers with Black Socks and Jeans

The great thing about chunky loafers is that they looks great with socks, so I the fall when it’s cold, you can cover your ankles and still be on trend.

Colorful Socks with Chunky Loafers
A Pop of Colorful Socks with Chunky Loafers

All black outfits are always sleek, but black leather pants with a pop of color like red socks and a matching lip, takes this chunky loafers outfit to another level. I am obsessed with this and filing it in my brain for another day.

Fall mini skirt outfit with loafers
Try Warm Tones with Your Chunky Loafers

The most common chunky loafer out there is black, but that doesn’t mean you can’t lean into the warm tones of fall! I love how she offset her black loafers with a brown sweater and plaid skirt. Or, go all in and snag a pair of brown loafers.

Shop Chunky Loafers

Nice to Meet You

Hi, I'm Camille! I'm a bi-coastal blogger splitting my time between LA and NYC and sharing elevated, yet relatable ideas so that you can achieve your most stylish life.

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