Timberland boots are the ultimate style staple for many members of the Black and Latino communities in New York City. It is as if they are part of some unofficial uniform. I remember growing up and seeing that most of my classmates would choose Timbs over a snow boot during the winter. And once the weather warmed up, the boots would still be in rotation — just head to Coney Island in the summer, and you'll see that it's never too hot to rock them. 

The boots were a fashion statement, and hip-hop culture helped solidify their status. Everyone from Jay-Z to Jennifer Lopez rocked them, so you had to own a pair. I wore them in my childhood, and when I got the chance to try three pairs as an adult, nostalgia set in, and I had to go for it.

The first pair that I wore were the classic yellow construction boots, which made me feel like a badass in an instant.

timberland construction boots
photo: Brittany Fowler

Timberland Women's 6-Inch Premium Waterproof Boots in Wheat Nubuck ($170, Timberland).

There's just something about the shoe's New York history that just brings out your innermost "don't mess with me" attitude.

timberland construction boots
photo: Brittany Fowler

 Whether it's snow or people, they'll get the message loud and clear.

Just look at this pose! It's like I'm ready to drop a mixtape at the end of this post.

construction boots
photo: Brittany Fowler

But once my initial euphoria subsided, I started to feel very uncomfortable.

Even though I was able to slip the boots on after loosening the laces substantially to accommodate my wide feet, and wore them outdoors to take photos, it wasn't until I was on my train ride home that I noticed an intense throbbing sensation.

I could feel the blood pumping through my veins as my feet begged to be released from the fresh hell they were currently occupying. I had no idea that these boots needed a long breaking in period and was completely unprepared. If I could have ripped them off and gone barefoot on the train, I would have.

The second day wasn't any easier, and as you can see in this picture, even my laces had given up on me.

timberland boots
photo: Brittany Fowler

The boots were still painful to wear, and it made me realize why so many people that own them seem to have such a tough exterior — wearing these shoes in isn't for the faint of heart.

At the end of the day, however, these are meant to be work boots and their hardcore durability comes at a price. I wasn't going to go down without a fight, so I soldiered on and wore them for a third day.

timberland boots
photo: Marissa Pina

I channeled J.Lo for my look, and even though they still needed to be broken in some more, I could start to see the light. I'm definitely not giving up on these boots!

timberland boots
photo: Marissa Pina

The thick rubber outsole has amazing traction. It will get me through light snow days and times when I want to add some New York attitude to my casual looks.

For my next challenge, I picked a pair with a chunky heel for a more dressed up option. Who doesn't want to wear Timbs on date night?

timberland boots heels
photo: Marissa Pina

Timberland Women's Glancy 6-Inch Boots in Black Nubuck ($130; Timberland).

Fortunately, this pair felt so much better straight out of the gate.

Chunky heels really balance my thick legs, and the moderate 3-inch height of this pair made them comfortable enough for me to get around the city without wanting to rip them off.

I can definitely see myself reaching for this boot over and over again.

timberland glancy boots
photo: Marissa Pina

It totally fits my style, since I love a good tunic with a pair of black leggings or skinny jeans, and this boot blends in seamlessly while giving me some extra height.

Lastly, I tried the Kenniston boots. They look sleeker and feel completely weightless — I think the shoe box was heavier, that's how light they are — compared to the classic construction boot.

Timberland boots
photo: Marissa Pina

Timberland Women's Kenniston 6-Inch Lace-Up Boots in White Full-Grain ($140; Timberland).

When I first slipped my foot into the boot, the fit was incredibly tight, and I immediately got flashbacks to my initial traumatic experience.

There was no way that I was going to put myself through another painful breaking-in period.

But thanks to the incredibly light leather material, it only took a few minutes for it to feel like I wasn't wearing a thing.

timberland boots
photo: Marissa Pina

Because of the pain-free experience, it quickly became my favorite pair out of the bunch. The light color, which is great for breaking up the dark colors I tend to wear on an everyday basis, was the cherry on top.

white timberland boots
photo: Marissa Pina

The third time was certainly the charm, and now that I've found my favorite style, I can officially reclaim my New York card.