Styling Square-Toe Boots

I refrained from buying square-toe boots because I thought this fad would disappear soon. But months later, square-toe boots still kept popping up in my feed. There were two possibilities for this. One: algorithms really understood me. Two: square-toe boots were here to stay (at least for a while).

Although the former is probably the truth, I’m going to believe the square-toe boot trend will continue thriving because I’ve never felt so chic and trendy while wearing a pair of shoes.

As someone who has rocked the same pair of boots for eight years, my tried-and-true 1460 Doc Martens boots, I couldn’t picture myself in a different pair, especially in a heeled pair. Truth be told, I don’t walk in heels that well, but what better time to practice walking in heels than in quarantine? I’m staying home anyway, so I might as well feel comfy and chic at home or whenever I step out to run the occasional errand.

I bought the Vagabond Hedda booties. Their sleek and simple style drew my attention. Plus, I like how they have a blunt square-toe and a chunky-curved heel. The line down the middle front of the boots is similar to the one on Maison Margiela’s Tabi split-toe boots, which I would love to get my hands on one day. For the meantime, these Vagabond black leather boots will do with their retro feel.

Here’s How I Style Them:

Tommy Hilfiger joggers (similar), Uniqlo sweater, Topshop coat (similar), scarf (similar).

One of my favorite Instagram accounts is LE:APT, which is a Paris-based online store. Their clothing is based on neutral tones and modern silhouettes. Plus, they place an emphasis on bridging the gap between chic and comfort.

Seeing how they styled minimal loungewear floored me and I had to try it for myself. I like how comfortable, yet elegant this particular look is and how it completes into a fit that says, “Lounging, but still luxurious and classic.”

For this look, I wore joggers that cinch at the ankles and reveal the sleek boots. I paired the joggers with a light lavender Uniqlo sweater that feels like cloud nine to the touch. I threw on a large Topshop coat with a chunky knit scarf that adds to the effortless feel of the outfit.

I love the bagginess of the look and how it pairs elements from classic menswear, like the sporty sweats, with a touch of sophistication emulated by the long coat and boots.


Gap jeans (similar), Zara oversized shirt (similar), Uniqlo turtleneck, thrifted denim jacket (similar), Intentionally Blank hat.

I stumbled upon the Aesthetics Wiki page and found an aesthetic that defines some of my occasional looks: the Light Academia aesthetic.

When envisioning someone rocking the Light Academia aesthetic, think of turtlenecks, dress shirts, and neutral colors. Just like the name implies, lovers of Light Academia spend their time reading, strolling in museums, and daydreaming. I put together my own look based on this aesthetic, which is my favorite way to style my square-toe boots. It’s the perfect everyday outfit!

I wore my cropped white jeans with a matching oversized dress shirt that I tucked in halfway for dimension. I slipped on a black turtleneck underneath, which not only kept me cozy and warm, but also added a nice contrast to the overall milky-white outfit. To make the look more casual, I threw on an oversized denim jacket and a cap, which made me feel like a hip carpenter that loves to paint on the side.


Marc Jacobs skirt (similar), lace blouse (similar), fur vest (similar).

Ahhh, the last look in this series is a very winter-y look, ideal for a holiday shinding, or even Game of Thrones cosplay.

The Oscar in this look goes to the iconic fur vest, which is the shining star that pairs well with the tweed skirt. The vest is extra, bold, and surprisingly warm, which is why I wore a light lace top underneath.

Sadly, I won’t be going to any shindigs this holiday season, but hey! Why not dress up for fun?


I hope you all enjoyed this post. Let me know how long you think the square-toe boots trend will last!

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