In partnership with Huckberry
Nepo babies get a lot of flack, but I for one am totally in favor of celebrating a talented offspring. I’m not talking about actors —though I do give Jack Quaid in The Boys a pass. No, I’m talking about fashion.
Take the chukka sneaker boot.
Hailing from #SGapproved lineage of the venerated chukka boot and a stylish, low-profile sneaker, this hybrid footwear heir deserves its flowers.
Maybe you’re not a loafer guy but want a shoe for those in-between professional and social occasions. When neither a repurposed running shoe or a stuffy lace-up will do.
Or maybe you’ve got weak ankles and need a little extra support! No judgment!
Whatever the reason, chukka sneaker boots might just be the footwear you’ve been looking for.
This shoe, known as CSB from here on out, combines a variety of elements from different styles to make its own stylish statement.
I love the moccasin stitching on this Luca pair, available on Huckberry. How the chukka laces keep it from being too sporty, while the rubber sneaker bottom can definitely handle you pounding the pavement on a daily basis better than a dressier sole.
Because of its nepo baby DNA, the CSB can easily fit into plenty of occasions and outfit scenarios.
Can you wear it to work?
To the right office, sure!
On a date? Definitely.
A weekend get-together at a bar or friend’s backyard? Absolutely.
Below, a week of chukka sneaker boot outfit ideas to try for yourself:
Perfect for a casual night out
Shop the outfit:
- pocket tee: Flint and Tinder
- denim jacket: Flint and Tinder
- shoes: Luca
- pants: Service Works
Did someone say trivia? Meet up with your sitcom crew in casual staples—a denim jacket, pocket tee, and straight-leg pants feel a little more special with these rich leather kicks over your standard sneaker.
Great for your business casual workplace
Shop the outfit:
- jeans: Flint and Tinder
- knit blazer: Faherty
- shoes: Luca
- knit polo: Wills
- watch: Seiko
Make sure you look and feel good for that big presentation with not-quite-white jeans and a knit polo and blazer combo on top.
In fact, don’t be surprised if the client ask you to send them the deck and a link to the shoes when you’re all done.
Just right for a first date
Shop the outfit:
- chinos: Wythe New York
- crewneck sweatshirt: Trumbull
- shoes: Luca
- t-shirt: Wills
- ID bracelet: LHN Jewelry
If this is the first time you’re meeting someone, it’s always a good idea to wear something you know you’re comfortable in (so you’re not fidgeting and self-conscious) yet feels just a little nicer than your usual look (so you’re putting your best foot forward).
These shoes are a nice medium between sneaker and dress shoe, so they can easily work in whatever setting you two choose.
A life of the party look
Shop the outfit:
- overshirt: Wax London
- ribbed tank top: Freenote Cloth
- shoes: Luca
- jeans: Hiroshi Kato
- sunglasses: Sunski
- braided leather belt: Corridor
In the right sneaker boot outfit, you’ll be the talk of the town! Keep it easy breezy in jeans and the statement overshirt that always gets you the most compliments.
Always-right office attire
Shop the outfit:
- sweater: Flint and Tinder
- Oxford shirt: Taylor Stitch
- shoes: Luca
- pants: Marine Layer
You KNOW loafers would work with your OCBD, crewneck sweater, and work pants at the office, but we’re always here to show you another way to wear your faves! The SCB gives these smart pieces a much more laid-back—but still ‘will get you that by EOD’—vibe.
Explore more casual style resources from SG HQ:
It’s Time to Embrace Cargo Pants (Again)
This 2000’s Era Sneaker is Back
The Guy’s Guide to Black Jeans
