Okay folks, let’s talk shoes. Specifically, high heels. Yeah, I know, sometimes they feel like torture devices. But honestly? I wanted to figure out this whole “matching heels to outfits” thing without looking like I tried too hard. My usual move? Grab the black patent ones and hope for the best. Spoiler alert: it doesn’t always work. Here’s how my little experiment went down.

Starting Simple (And Messing Up)
Looked in my closet yesterday morning. Found this nice flowy floral dress I bought ages ago. Soft colors, summer vibes. Felt good, you know? Then I pulled out my go-to pair: big, chunky block heels. You know the type – sturdy, feel kinda platform-ish, heavy. Put them on. Looked in the mirror… and it felt off. Like wearing hiking boots to the ballet. Seriously, the dress was all light and airy, and these shoes? Total bricks. Ruined the whole floaty feel.
Swapped them out for my strappy sandals with the skinny stiletto heel. Much better! The delicate straps actually matched the dress’s vibe. Made my legs look longer too. Lesson number one? Heavier shoes killed the light outfit. Thinner heels saved it.
Testing the Work Pants Conundrum
Later that day, putting together a work look. Grey tailored pants, crisp white button-down shirt. Professional, sharp. I usually wear boring flats, wanted something smarter. Remembered those chunky heels from earlier. Figured they needed a win. Tried them. Boom. Perfect! The chunkiness actually balanced the straight lines of the pants. Made me feel grounded and powerful, not wobbly like stilettos sometimes do.
Actually, thought about stilettos. Tried a pair. With the tailored pants? Nope. Felt kinda aggressive? Like I was trying too hard to be sexy instead of competent. Chunky heels won this round.
Denim Day & The Ankle Strap Dilemma
Weekend time. My favorite skinny jeans and a plain tee. Casual. Had these pumps with a thin ankle strap. Popped them on. Didn’t hate it, but something wasn’t clicking. They felt a bit… dressy? For a tee? Dug deeper in the shoe pile. Found some classic pumps – simple pointed toe, no strap at all. These felt way more relaxed with the jeans and tee. Less fussy.

Later tried wearing those ankle strap heels with a flowy midi skirt. Winner! The strap actually complimented the skirt’s hem and felt more balanced.
Got curious. Tried a skirt with those plain pumps? Felt unfinished, somehow. Needed that little something the strap provided. So yeah, straps matter depending on the hemline and vibe.
Messing with Platforms & Proportions
Feeling bold. Pulled out these platform sandals I impulse-bought. They’re… substantial. Big sole, thick heel, serious presence. Felt intimidated. Paired them with a bodycon mini dress I rarely wear. Honestly? Awesome! The chunkiness of the sandal played well against the fitted dress. Made it feel more modern and balanced – less “going out,” more “knows what she wants.”
Tried the platforms with loose linen pants? Disaster. Felt like clown shoes. Just swallowed the whole outfit. Too much shoe, too little structure.
The Grand Summary (So Far)
Alright, here’s what my closet wrestling match taught me about not looking insane with heels:

- Flow = Thin: Light dresses, soft skirts? Skinny heels, strappy sandals all the way. Avoid the chonky ones.
- Structure = Chunky: Tailored pants, stiff fabrics? Block heels, even platforms sometimes, are your friend. Stilettos can look too harsh.
- Ankle Straps Mind the Gap: With pants or very short skirts? Maybe skip ‘em. With skirts hitting at the calf? Perfect pairing.
- Platforms Need Tightness: Big shoes need fitted clothes. Loose outfits get drowned by them.
- Pointed Toe = Elongating Magic: Honestly? Pointed toe heels, even with a little height, make legs look longer with ANYTHING compared to rounded toes.
So that’s my basic heel strategy now. It’s not rocket science, just gotta pay attention to the feel of the outfit and the shoe. Still prefer sneakers most days, but hey, at least now I can wear the fancy shoes without feeling like I’m mismatched!”