Thursday Boots Outfit: 9 Awesome Ways to Style Thursdays

What good is a pair of boots if you don’t have the style to back them up?

I love Thursday Boot Company, and I own 10 pairs myself (mostly different models). Because I wear Thursdays so often, I’ve thought a lot about how to put together the perfect Thursday boots outfit. 

Below, I’m going to outline a few basics to consider when styling your Thursday boots, plus show you nine outfits I personally love to wear with my Thursdays. And this isn’t just for the Captain—I’m showing how I rock several different styles of Thursdays. 

Here’s What to Wear With Thursday Boots

Tapered, Slim Fit Trousers

Because Thursday boots are more casual, you can rock any style of pants you want, but the key is to keep them slim and tapered. 

I like slim fit jeans with taper below the knee, but if you’re in your 20s, you can still rock skinny jeans, so that’s a good option, too. 

Avoid straight cut or boot cut jeans with Thursday boots. Because Thursdays are slim and relatively narrow boots, they look best when your outfit is more streamlined. Too much fabric around the bottom of your pants, and your boots will get swallowed. 

Most slim fit jeans have moderate taper below the knee, and skinny jeans typically have the most taper below the knee. I personally like more taper below the knee because I have larger legs. The extra taper helps me look taller and less wide. But if I push the taper too far, I just look top-heavy. It’s a balancing act.

Don’t just box yourself in with jeans, though. The beauty of Thursday boots is that you can wear just about any style of pants. 

I also love wearing chinos with my Thursday boots. However, make sure your chinos have decent taper below the knee and you’ll be set. 

You can also wear canvas pants and work trousers with Thursdays if you’re going for the full rugged style. 

Shirts

A solid t-shirt to match with your pants is all you really need, but if you haven’t already, I highly recommend getting at least one overshirt you absolutely love. 

And don’t be afraid to spend a little on an amazing overshirt because it’ll last you forever and you’ll wear it often. 

I have about three overshirts that I rely on throughout the fall, winter, and spring. Yes, they were a bit of a stretch on the budget, but I get so much use out of them that they’re worth it. And they define my style. 

I also like to have a few buttoned shirts for warmer days and layering. A light wash denim shirt and an oxford will do the trick.

Accessories

This is up to you and your personal style. I’ve seen dudes rock huge signet rings, bracelets, and necklaces with their Thursdays and look awesome. 

Me? I stick with a good watch. But there is appeal to those sweet signet rings that’s calling me. 

Because Thursday boots are on the line between classy, casual, and rugged, you can really inject your personal style into whatever outfit you want to wear. If you like to wear a lot of accessories, go for it. If you’re more minimalist, that’ll work, too. 

How to Style Thursday Boots

Styling the Thursday Boots Captain

The Captain is Thursday’s most popular boot, and it’s also one of the most versatile options. In the video above, you can see five different ways of styling them, but I’ll also post more examples below. 

I own three pairs of Captains: Arizona Adobe, Brown, and Tobacco Storm King.

I like my Arizona Adobe Captains the most.

In the outfit above, I’m rocking a take on business casual, but emphasizing the casual aspect. 

I’m wearing slim fit chinos, an oxford cloth button down, and a light overshirt. Of course, I’m wearing my Arizona Adobe Captains on foot. You can absolutely mix brown and grey, especially with blue, as those are all neutral colors. 

The keys to this outfit are that the chinos are slim and use a relatively thick fabric, and the overshirt is ironed out. Too many wrinkles and this outfit falls apart. Keep everything crisp, and it’s an easy but put-together look. 

I also like to wear denim-on-denim with my Thursday Captains. But try to keep the denim colors a little different on top and bottom. I’m cutting it close in the image above—choosing black and blue denim would be safer. I’m also wearing a heavily textured sweater underneath, which gives the outfit some depth. 

The outfit above is one of my favorites because it’s so easy: a pair of slim fit chinos (these are from Taylor Stitch), and a simple light wash denim shirt. This would look even better with more accessories like a bracelet and maybe a few extra rings. 

The Storm King is a little different because the sole is so pronounced compared to the regular Captain. 

With the Captain Storm King, I beef up the rest of my wardrobe to match. I’m wearing a heavy canvas overshirt and a pair of heavy canvas work pants. As a bottom layer, I have a crew-neck sweatshirt. Every item is from Taylor Stitch, which is a fantastic brand to browse if you’re looking for something to pair with your Thursdays. 

You can probably see a pattern in my outfits: slim fit pants, structured overshirt, textured bottom layer. It’s a solid combo that wins every time, and you can adjust the weight of your clothes based on the season. 

Styling the Thursday Cavalier

The Thursday Cavalier is the brand’s dressiest Chelsea, but how you style it depends on the leather option you choose. 

If you have the Shadow Grey suede or Chocolate suede, then I’d stick with more casual looks. But the full grain leathers like Black are dressy enough to rock with a suit. 

Because I have a suede Cavalier, I stay simple: slim fit jeans with a dark colored Oxford shirt. I stay in greyscale. I’ll also wear a white t-shirt with the same jeans if it’s warm enough to skip the long sleeves. 

Chelsea boots like the Cavalier naturally look a little more classy, so you can get away with looks that don’t require as much effort. A basic tee and jeans will look elevated because of your Chelsea boots.

Check out a few of my favorite ways to style Chelsea boots (the Thursday Cavalier and Duke included) in my video below:

Styling the Thursday Diplomat

Moc toe boots are nice to have for fall and winter looks. I rarely wear moc toes in spring and summer, though the Diplomat looks great no matter when you wear it. But if you want to stick strictly to the style rules, save your Diplomats for the colder months.  

Because it’s colder, layers are necessary, and you’ll probably want thicker fabrics. Here are the three basic rules of layering for guys:

• Lightweight fabrics stay closer in toward your body, and heavier fabrics stay farther away
• Light colored fabrics stay closer, and dark colored are farther out
• The more patterned, the farther out—keep your bottom layers solid, neutral colors

If you like your jeans with more of a straight fit, the Diplomat is beefy enough to handle the style. I find that the Diplomat is closer to heritage brands like Red Wing and Wolverine in terms of bulk on the foot. 

But it’s still much slimmer, so I still recommend slim fit jeans or chinos.

To see how the style of the Diplomat compares to other major brands like Red Wing, Danner, and Thorogood, check out my video comparison of the top moc toe boots below:

Styling the Thursday Duke

The Thursday Duke quickly became my favorite everyday Chelsea boot. While the Cavalier is better suited to extremes: either paired with a suit or going full grunge with a ripped pair of jeans and a slubby tee, I think the Duke is better for the middle ground.

I really like the Duke in Honey suede. It’s casual and versatile—I wear these boots through fall, winter, and spring (you can wear them in summer, but I usually wear sneakers in the hottest months). 

In the picture above, I’m going denim on denim again. The key is a nice denim jacket. Because suede Chelsea boots are casual, I’m cuffing my jeans. The cuff also helps keep too much indigo dye from rubbing off on the suede, though a little indigo on your boots is inevitable with the light color of the Honey suede. 

Styling the Thursday Explorer

The Thursday Explorer is probably the brand’s least versatile boot, but I love it anyway. 

It has a modern combat boot style, so leaning into a military aesthetic is a good move. In the outfit I’m wearing with the Explorer, I have a t-shirt, a light waxed jacket, and a heavier quilted bomber on top.

I really like the pairing of mustard yellow and olive green. The green of my jacket matches well with the Dark Olive suede on my Explorers.

I like to do a double cuff with my jeans to show off as much of the boot shaft as I can. Because I think it looks cool. What’s the point of the padded ankle if you’re not going to show it? 

Jeans are considered neutral, so this outfit really just works with two colors: green and yellow. 

Styling the Thursday Loggers

The Thursday Logger is another high-shaft boot: eight inches instead of the standard six. 

Lean into the lumber-jack look with a high quality flannel (the one I’m wearing above is called the Blanket Shirt from Outerknown). 

I’m also wearing a pair of selvedge jeans, which are widely regarded as some of the best quality you can find in denim.

Boots like the Thursday Logger and Explorer look great with a double roll, or any pair of pants that breaks above the ankle. I also love to wear my Loggers with a pair of light cotton work pants. 

These have a military-esque feel to them that works really well with the sturdy waxed leather of the Thursday Logger.

Styling the Thursday Scout

I’ve never been a huge fan of chukkas, but the Scout is the only chukka I own that I actually wear. I’ll say this: they’re excellent spring, summer, and fall boots. 

I have the Scout chukka in Mocha suede and I like the burnished toe and heel. In the image above, I’m wearing olive chinos, a heavy canvas overshirt, and a leather jacket on top. 

Do you have any go-to color combos? A favorite of mine is mustard, olive, and brown. It works with my skin tone and always matches a pair of boots. 

Like with other Thursday boots, the Scout looks best when your pants have taper below the knee. I like to show off a little more of the leather at the ankle, so even if your pants have a clean break, you can give them a cuff to expose more leather. Just make sure you have cool socks to back it up. 

Brands I Like to Pair with Thursday Boots

If you’re wondering where to start shopping, these are the brands I wear all the time with my Thursday boots. They’re my favorite brands to shop with.

If I’ve learned anything, it’s that I’m way better off buying one more expensive shirt that I love and that I’ll wear all the time than I am pinching pennies and buying two decent shirts. 

You’ll notice throughout the images in this article that I’m wearing a lot of the same clothes with different outfits. I don’t really have a huge range of clothes—just a few select pieces that are super high quality and fit me well. It took me a long time to realize that’s the best way of going.

For clothes, try Taylor Stitch. They have a similar balance of modern and rugged that I think matches up with Thursday really well. Their shirts and jackets are pretty unanimously awesome, but not all of their pants have as much taper as I like to have with Thursday boots. 

The green chinos I’m wearing in a lot of the above pictures are from Taylor Stitch, but I have to cuff them because their inseams are 34” (so you have to hem them to get them down to size). 

I also really like Outerknown for their Blanket Shirt. They also have great t-shirts. The best t-shirts I’ve ever owned are from Goodlife, but they’re expensive. I own a few Goodlife tees, but the majority of my tees come from Fresh Clean Tees. Those are more affordable (better for undershirts).

VAER watches remind me a lot of Thursday Boot Company. Their team is super small and very dedicated to delivering an amazing product at a low cost. You can’t tell, but in most of the images above, I’m wearing a VAER watch. I own three or four and can’t recommend them enough. 

Other than those brands, I just supplement my wardrobe from GAP and Banana Republic with basic pieces.

But the best statement pieces come from:

• Taylor Stitch
• Outerknown
• Goodlife
• VAER

Over and Outfit

The biggest reason I wear Thursday boots so often is because they’re versatile and relaxed. But they’re not totally rugged, either. There’s a bit of refinement in their style.

You can choose to go as simple as a t-shirt and a pair of jeans with your Thursdays, or you can get more elaborate with overshirts and accessories. 

But if you have a great looking pair of boots on, it’s hard not to look great. So what are you wearing? 

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