One year ago when I bought them, I never would have thought my lug sole chelsea boots would become my most-worn boot. But they are truly my go-to. I style them with everything from dresses to denim and classic to more trendy outfits. So, when a few readers requested lug sole chelsea boot outfits, I was happy to feature them in one of my style sessions!

Lug Sole Chelsea Boot Outfits

Although they are a little bulkier and heavier than your classic chelsea-style boot, I’ve found the lug sole version to be just as wearable and versatile. Plus, there is something so easy about a slip-on ankle boot! And when I’m running out the door, ease and function are often just as important as style!

My exact boots also come in classic black leather, but I personally have been opting for warmer tones this fall. And the brown of the boots are the perfect color to go with everything from creams and tans to darker browns and even black. I find them to fit TTS, but if you plan to wear them with thicker sweater-style socks, I recommend sizing up 1/2. If you’re interested in more of a combat boot, be sure to check out my combat boot outfits!

Button Up and Straight Leg Jeans

This combination is a timeless one and the perfect base for adding layers! While I kept it simple here, I’d also layer with a long sweater blazer (see seven sweater blazer outfits!), a leather jacket (five brown leather jacket outfits here!), a chunky cardigan, or utility jacket.

Because these straight leg jeans are slightly slimmer through the leg, I cuffed the hems. I prefer for there to be a contrast between the shaft of the boot and pant leg. For slimmer legs, adding a cuff adds a clearer delineation between boot and pant leg. You can see more examples of this in the skinny jean version below or the last outfit, which has a wider straight leg.

Fall Maxi Dress and Lug Sole Chelsea Boots

Anyone else really into dark floral dresses? I love them for fall and winter, especially when paired with rich tones like this leather jacket and lug sole chelsea boots! They add a touch of softness to a chunkier boot. I’d also wear this dress layered with a cardigan! (You can see an example of that look here!)

Oversized Turtleneck and Skinny Jeans Outfit

Skinny jeans are another great option to pair with lug sole chelsea boots! But for this style of denim, I suggest either tucking inside the boot layered with a chunky sock or creating a cuff! If you chose to cuff, make sure to show a bit of skin between the bottom of the pant leg and boot! Or if your jeans are the perfect cropped length, you’re good to go. This is all about creating that contrast between pant leg and boot shaft!

Shirt Dress and Lug Sole Chelsea Boots

Another dress option for ya! This one is a classic shirt dress style that I layered up with a cozy cardigan. Contrastingly to the midi dress, this cut is not flowy or long but it still works with the boots! A straight-fitting skirt would create a similar silhouette! If you want to create an even cozier vibe, you can also layer with a slouched sweater sock!

Shirt Jacket and Straight Leg Jeans

Here is the last denim style that I wanted to share with you! You can tell that the leg is wider than the other two and the structure of the pant leg is wider than the boot shaft. You could always still cuff if you’d like, but I like it just as is with this style of wider straight leg denim.

Be sure to check out the other posts in my style session series, where I style one item in my closet multiple ways!