25 Under-$150 Shoes You Better Believe I'm Currently Eyeing

Most Wanted is a weekly series in which one Who What Wear team member or friend of the brand will share the top 25 finds on their current wish list.

I’ve harped on and on about how my style always veers more toward classic looks: ballet flats, classic gold jewelry, the list goes on. So when a trend hits, I take longer to pick it up (if I even do at all). This season? That trend is chunky shoes, specifically chunky-soled boots. Going from the softer silhouette of a ballet flat or loafer to a chunky and heavy shoe felt like a huge change for me, but there was something about it that kept making me rethink the trend. TBH, they remind me of the platform, extra-chunky shoes I used to wear in the '90s and early '00's, specifically from Steve Madden.

I had a change of heart while I was scouring the internet for a pair of winter boots and landed on this pair. Sure, they're not the exact definition of a lug sole, but the heel is a solid block and a nice transition for me into the world of chunky-sole shoes. What makes shopping for a trend I'm still testing easier is that I can use Shop Pay’s installments feature in partnership with Affirm, for a flexible and transparent way to pay later for whatever I'm shopping for. All I have to do is select Shop Pay at checkout and choose to pay in 4 installments. Best of all, paying later won’t impact my credit score, is interest-free and has no hidden fees. So from thick block heels to a true lug sole (and even a few sneakers), these are the 25 under-$150 pairs I have my eye on for when I'm ready to take the plunge.

The heel on this point-toe ankle boot is super chunky, but what I love about the shoe is how easily it can be worn with a pair of wider-leg jeans. 

With Shop Pay, get them for four interest-free payments of $37.48

While I'm slowly entering lug-sole territory, this option has just the right amount of lift.

With Shop Pay, get them for four interest-free payments of $37.48

I've seen pairs similar to these white mock-crock embossed boots all over my IG feed, and I have to say, these are perfect to wear with a shorter skirt and a blazer with a pair of opaque tights.

With Shop Pay, get them for four interest-free payments of $28.73

If white boots like the ones above scare you, a black version is always a safe option. Style with a pair of baggy jeans.

With Shop Pay, get them for four interest-free payments of $32.48

A chunky Chelsea boot that is an easy transition from the block heels I have my eye on above. 

With Shop Pay, get them for four interest-free payments of $28.73

I've seen styles like this worn with long coats, and honestly, I'm considering putting together the same outfit for winter. 

With Shop Pay, get them for four interest-free payments of $44.98

A shorter version if you're not down for tall boots.

With Shop Pay, get them for four interest-free payments of $24.98

For those who are much braver than me, this mid-calf chunky boot is the most forward option of them all. 

With Shop Pay, get them for four interest-free payments of $47.48

Another lace-up, this moto-version is not for the faint of heart. 

With Shop Pay, get them for four interest-free payments of $24.98

A classic style with a platform twist. 

With Shop Pay, get them for four interest-free payments of $24.98

We're all aware of the loafer trend this season, but a chunky loafer seems even better to me. 

With Shop Pay, get them for four interest-free payments of $27.98

Two-toned and it has a lug sole. 

With Shop Pay, get them for four interest-free payments of $24.98

Chunky soles aren't reserved for just boots at Steve Madden. There's a slew of sneakers with a little bit of lift as well, and this neutral pair really stood out.

With Shop Pay, get them for four interest-free payments of $20.73

Notice the sole? I love the small touch of detail to these otherwise classic sneakers that work for people like me who swear by a timeless wardrobe. 

With Shop Pay, get them for four interest-free payments of $17.48

The OG platform sneaker—you can never go wrong with this option. 

With Shop Pay, get them for four interest-free payments of $17.48

For anyone who is looking for a shorter, more classic Chelsea boot with a block heel, I found one for you.

With Shop Pay, get them for four interest-free payments of $32.48

More Western-inspired, this slimmer boot still packs a punch with a slightly curved block heel. 

With Shop Pay, get them for four interest-free payments of $33.73

If you're not down to buy another pair of black boots, go for a taupe color.

With Shop Pay, get them for four interest-free payments of $33.73

A classic Chelsea boot, this heel is wide and not too extreme. 

With Shop Pay, get them for four interest-free payments of $32.48

Can never say no to a sock boot with a block heel for the winter months.

With Shop Pay, get them for four interest-free payments of $24.98

Another slightly curved block heel that I'm fully here for. 

With Shop Pay, get them for four interest-free payments of $24.98

I love the tortoise shell textured heel here to add a touch of height but still keep it chic. 

With Shop Pay, get them for four interest-free payments of $34.98

These are giving me all the '70s vibes, especially the cognac color and the wooden block heel.

With Shop Pay, get them for four interest-free payments of $44.98

If you wear a ton of neutral outfits like myself, a snake-print boot with a block heel is a great way to add some kind of "color" to your look.

With Shop Pay, get them for four interest-free payments of $29.98

Similar to the shoes I styled, this taller version can turn your outfit into a serious statement.

With Shop Pay, get them for four interest-free payments of $47.48

Selecting Affirm as a payment option is subject to eligibility check and approval. Estimated payment amount excludes taxes and shipping fees. Payment options through Affirm are provided by these lending partners.

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