5 Cool Ways to Wear Boots

5 Cool Ways to Wear Boots

Give boring outfits the boot
how to wear men's boots outfit ideas

By Gabi Meyers | Last Updated: Jan 23 2024 | 4 min read

how to wear men's boots

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:

how to wear men's boots outfit ideas
Look #1
how to wear boots outfit ideas

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
how to wear men's boots outfit ideas

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
men's boots outfit ideas

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
how to wear men's boots

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
how to wear men's boots outfits

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.


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.


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

Like a phoenix rising from the ashes, Gabi Meyers went from Team SG's first-ever intern to a trusted fashion editor and stylist. She currently lives in Chicago with a very cute dog.