Not sure about you, but up until recently I equated dress shoes with high levels of style but low levels of comfort. The most classic men’s shoe in the game is definitely an essential, but the bone-breaking process of breaking them in can be frustrating and painful. Thankfully there are now brand like Wolf & Shepherd, a shoe company that is specializing in creating extremely high quality boots and shoes that look great – but also feel great, too. They noticed that a lot of guys were traveling to and from work in sneakers, only to then put their dress shoes on once they reached the office. Their solution…develop a line of dress shoes and boots that look tough, masculine, and classy, but feel like you’re wearing your most comfortable pair of white sneaks.

I’ve styled two different pairs of Wolf & Shepherd shoes for you guys today to showcase the fact that looking good doesn’t need to hurt.

In the first look I styled these chukka boots. I first gravitated towards them because the leather looks like a really fresh basketball. Once I put them on I realized how amazing the design really is. The insole is incredibly soft so I could be on my feet all day and not need to worry about blisters or aching heels, both of which are often issues for me.

A chukka boot like this is often going to work best styled casually, so I thought that some slim corduroys, a white henley, and this brown suit vest all worked well to stay casual, comfortable, but stylish. I’m a big believer in dressing for success, so even if you work in a casual environment or (like me) from home, being sure to try and look your best will lead to meeting your goals more quickly. Just because you don’t have a strict dress code, you shouldn’t show up in sloppy jeans and a tee. Enforce a code for yourself and see how much more productive you become.

A chukka is an absolute essential style for every guys closet. They’re a great weekend shoe that can be styled with denim, chinos, trousers…pretty much whatever you’re going to be wearing outside of a formal suit. On those days when a sneaker just feels a bit sloppy, embrace your grown man game with some chukka boots. Plus, when they’re as comfortable as this pair you don’t have to compromise.

In the next look I opted for the Wolf & Shepherd Chelsea Boots. You may already own chelsea’s considering how popular they’ve become, but what I love about this pair is that they’re a bit more dressy than a lot of others I’ve seen. The shined leather, slim toe box, and extra high top cut all lend to being extremely versatile. I styled them casually with the khaki denim, brown marled long sleeve tee, and blue patterned blazer, but they would also work really well with a suit.

If you do feel like you’d prefer to style this shoe in a more dressy way,  be sure that you keep the leather nice and polished. The more scuffed and dirty they get the less dressy they become. Similarly to the chukka, these feel completely broken in from the very first wear. I love chelsea boots but they can sometimes be troublesome in the first few wears before they form to your foot. These slid right on and felt like I’d worn them 10 times already.

With the boot being so high, it’s a fun move to cuff your pants up a few times to show off the height. Let the cuff rest just below the top of your boot when you’re standing and it adds a nice extra little touch of style to your outfit. Casual is my go-to as you guys know, but this is a look that I’d feel totally comfortable wearing in most settings.

Getting yourself a great, reliable pair of investment boots like this is a great idea because you’re going to get a ton of opportunities to wear them. Also, the same goes for dress shoes. Although I didn’t showcase any today, Wolf & Shepherd also offer some amazing lace up dress shoes, loafers, and military style boots. Think of your dress shoes as an investment in yourself. If you wear them every single day, you shouldn’t be pinching pennies. You should get the best possible thing to help you look your best, feel your best, and something you can trust will last you a lifetime if you take care of it like you should. Wolf & Shepherd checks all of those boxes.

Be sure to check out Wolf & Shepherd to see the rest of the styles they offer as well as the ones I showed you today.

I hope this was informative!

Questions? Comments? Find me on social media @parkeryorksmith or email me at!

As always – do it for you, not them!


About the author

I'm Parker York Smith, a curious dude still very much figuring everything out. I hail from the Midwest but have been dwelling in Los Angeles for the last few years being a pretty stereotypical west coast transplant. I'm a fashion geek, I love to walk (a LOT) and I do my best to find the bright side. I'm extremely excited about this blog and hope that (with some hard work and luck) it turns into what I believe it can. If you have any questions, comments or concerns, please get in touch with me via my social networks (which can be found in the sidebar) or email me at

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