5 Days 5 Ways

5 Cool Ways to Wear Boots

Give boring outfits the boot

By Gabi Meyers | Last Updated: Nov 23 2020

If, like me, you’ve been living in sweatpants since spring, actually leaving the house feels more like a fashion show than ever before.

While you may find yourself on unsteady fashion footing—is everyone still wearing slim-straight pants? What is a noragi jacket?—you still want to look good, and you want that to be easy.

One way to ensure you’ll look and feel like a million bucks? Pulling on footwear that packs a punch (or is it a kick?). 

In cold-weather months, a bold statement boot makes the perfect outfit starting point.

You can pair an eye-catching boot with a casual, laid-back ‘fit, or go all in with a head-to-literal-toe O U T F I T inspired by your fashion-forward footwear.

We recently partnered with Texas-based shoe brand Taft on a Pinterest campaign (psst, do you follow us on Pinterest? It’s a great place for outfit inspo!!), showing a few ways to wear their offerings. From hand-woven leather Jodhpur boots to the perfect combat-sole boot, these things are ::chef’s kiss:: good.

And honestly, guys? I couldn’t bear the thought of not sharing a few of my favorites in a 5 Days 5 Ways feature right here on SG dot com.

These outfits are perfect for the holidays, whether you’re celebrating in-person with your immediate family, or checking in with the fam on Zoom.

How to wear five different statement men’s boots five ways:

Look #1

boots | sweater | pants | socks | bandana

SG Says: If you want equal parts refined and cozy, these wool boots are it.

For a fireside-worthy fit, pair with a classic fisherman sweater and some crisp plaid trousers. If you do think you might find yourself kicking off your boots, make sure you have some equally interesting socks. 

Look #2

boots | camp shirt | pants | work jacket | sweatshirt | hat

SG Says: Megan was ~not~ sure about these brown corduroy separates, but I do what I want!

Play up the bold houndstooth print of the boot with a complementary color scheme. Because while a red crocodile print camp shirt may seem loud, the rest of the outfit has a nicely muted palette.

Living in a chilly locale? Layer an oatmeal-hued sweatshirt between to warm up you and your look. 

Look #3

boots |t-shirt | jeans | cardigan | belt

SG Says: These jacquard weave boots look like they’ve lived an interesting life, so take a cue from them and throw it back.

A classic crewneck tee, hefty cardigan and selvedge denim make an immediately timeless look.

Look #4

boots | pants | mask | shirt | vest

SG Says: Excited to go outdoors? Dress the part!

Even if you’re just taking a walk around the (city) block, camo pants and a highlighter vest give you the feeling of being deep in the woods. Woven leather boots give this otherwise casual look an elevated air.

Look #5

boots | kimono | sweatpants | henley | sunglasses | mask

SG Says: We’re still in covid times, so don’t be afraid to have a sweatpants moment while you can.

Swathe yourself in such visibly textured fabrics that just seeing them feels like touching them—that way you can maintain six feet distance AND style.

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Want to know how to wear men’s boots in more ways? Check out this #SGapproved guide to Chelsea boots, and our favorite winter boots.

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This post not sponsored, but our partnership with Taft on Pinterest was; thanks for supporting the brands that make Style Girlfriend possible!