Style Timberland Boots 4 Ways

They must be the chunkiest boots on the face of this earth but these Timberlands don’t necessarily need to be styled casually. Though they are often associated with an outdoorsy sort of comfort in style look, I thought I’d pair them with various outfits in my wardrobe, none of which fit the classic Timberland ad but in doing so, I found them a lot more versatile than I had thought. Buying these boots was a practical decision. They are seriously warm and perfect for below freezing temperatures and icy streets from snow days. I don’t know how I survived winters without them. They are definitely an investment as they don’t come in cheap. But if you have a fear of walking on the streets and falling all over the place with your hot Starbucks in hand (cough cough) then you might wanna look into getting yourself a pair.

Here’s how I styled my black Timberland boots in 4 different ways.

The Casual Look


Let’s begin with the obvious. Dressing casually & wearing Timbs seem to go hand-in-hand and I think for good reason. These boots are surprisingly comfortable given their mere weighty appearance. But is it just me or do these black ones seem slimmer than the original camel colour ones. It might just be the good ‘ol black slimming effect that we often associate with tops & bottoms but to me, they don’t seem as bulky as I imagined. I’ve styled them with some Topshop Joni jeans, a simple Levi’s tee and an over-sized men’s jacket from Uniqlo to tie in with the masculinity of the boots so it’s a more rounded look. I especially love the contrast of the black skinny with the chunky boots as it just adds to the slimming effect we were playing on earlier.



The Party Look

Seeing that it is festive season & all why not wear your Timbs out to a fancy dinner or an office party. I’m such a home-body I don’t even know what types of parties people go to these days, but this is a more dressed up version of how I’d style these boots.


I think the key for me is throwing outfits together that I usually wear and putting on my Timberlands and see how that works. That’s how you know you’re keeping to your own style and not copying what everyone else is wearing. It also adds something extra to your look, something unexpected almost, and that’s what I love about these outfits. Here I’ve gone for a few of my favourite pieces, a black fitted high neck, a black slip dress and again an oversized men’s coat, because it is really cold outside.

I love any look which involves a slip dress and this is no different. The movement that it gives from its effortlessly light fabric with that bit of lace to spruce it up, the classic high neck which adds structure to a rather flowing piece, the over-sized coat draped around your shoulders and the boots to show that you’re different and that your style is unique. It’s some what tom boyish in a way and that’s what I like about it, dressing up but still not looking overly feminine. I think the boots and the coat add character to this outfit because they’re so different.


Out for Drinks

I’m pretty sure this look inspired this entire blog post and the photographs as well. It’s cool & effortless and a typical something-I-just-threw-on look. A sheer black blouse with embroidery details that always maks me feel good whenever I’m wearing it. It’s just an easy piece to throw on with skirts and jeans especially, to upgrade the look of them. Here again, I’ve paired it with my black skinny jeans because black on black always works for everyone and I just feel so comfortable in black. This look feels like me, like my own style.


When I run out for an evening meet up whether it’s post work or at the weekends, if the sun’s going down I like to look like I’ve put a bit more effort into my outfit and my make-up. To me, this look is too easy almost, it’s a fail proof outfit for an evening with friends. I would usually have preferred a black heeled boot for this look but I thought why not wear my Timberlands instead. I think it makes this outfit even cooler, like you really didn’t try at all. You can basically wear this outfit with any shoes you want but this is just what I went for and I love the way it turned out. I felt so comfortable in this look!


Let’s Talk Business

This must be my favourite look of all seeing that it is the one I’d never thought would work or one I wouldn’t necessarily associate with Timberland boots. Don’t get me wrong, Timberland do an amazing array of boots some of which are suited for a more business look. I do own a pair of heeled Timberlands which I love but this classic pair is proving to be more versatile than ever. There’s nothing in this world that a button down white shirt can’t go with, and if you’re running around going to meetings or to your office then who says your Timbs are too casual for business attire.


I think they work perfectly paired with these black skinnies, a classic white shirt and a coat all of which is worn to offices anyway, you’ve just got a bit of extra boot in your step. I think the Timberlands give off a stronger appearance and isn’t that what we want in business situations? So why not challenge yourself out of the usual office attire and give more love to those boots you worked so hard for. I think I’ll definitely get my wear out of them all year round.



Hope you enjoyed this post and thank you as always for reading! To all of you who consistently read this blog, I can’t thank you enough for all of your support  this year Xx

Wishing you an amazing 2018!

Photography by Jeff Simone




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