Products are curated by Style Girlfriend editors. Purchases through our links may earn us an affiliate commission.
If you work from home like me, actually leaving the house can feel more like a fashion show than ever before.
While you may find yourself on unsteady fashion footing—is everyone still wearing chore coats? Can I wear workwear pants if I’ve never swung a hammer?—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, having go-to ideas for how to wear men’s boots makes getting dressed easy.
You can pair an eye-catching boot with a casual, laid-back ‘fit, or go all in with a capital-O OUTFIT inspired by your fashion-forward footwear.
These outfits are perfect for fall and winter, whether you’re celebrating the holidays with your family or meeting friends for a night out.
How to wear six different statement men’s boots five ways:
Chelsea Boots
SG Says: If you want equal parts stylish and comfortable from your boots, this Blundstone pair fits the bill.
Add a trendy rugby shirt up top, and you’ve got yourself a nice l’il look.
Wallabee Boots
SG Says: A Wallabee boot makes for solid investment footwear.
Dress yours up with chinos or 5-pocket pants for an outfit you can wear at work or a date.
The workwear jacket gives a classic look a trendy impact.
Laced Boots
SG Says: Black leather lace-up boots look as good in an office as they do on the weekends.
To make this outfit more off-duty, swap the trousers for jeans or workwear pants.
chukka Boots
SG Says: Chukka boots have long been a favorite at SG HQ.
In 2024, pair yours with a vest and 5-pocket pants for a go-to casual look.
Hiking Boots
SG Says: Don’t be afraid to pair your boots with sweatpants, so long as they’re stylish and not sloppy.
The tapered ankles tuck nicely into a sturdy hiking boot. For the rest of the look? A simple pocket tee and denim jacket, topped off by a beanie.
Cowboy Boots
SG Says: Western wear isn’t going anywhere, so this could be the right time for you to try cowboy boots.
To prevent cowboy cosplay, go for modern and understated with the rest of your outfit.
