When Sneakers Simply Won't Do

I’ve been traveling so much for work and I struggle to choose which shoes to pack. I hate sneakers, but love comfort - so I polled some incredibly tasteful people about what shoes they turn to when they gotta walk far, but wanna look good.

Name: Drew Joiner

Title/profession: YouTuber/Content Creator

Handle: @drewjoiner

Brand: Danner Japan

Model: Danner Cascade Range 4

What compelled you to buy?: These shoes are something that I had my eye on for a little bit and once the opportunity arose to get them... I snagged them!

What kind of outfits does it pair well with/ badly with?: These can be paired in a ton of ways but they lean more towards heritage menswear blended with vintage outdoorism.

How long did they take to break in?: The shoes were incredibly comfortable right out of the box! They feature an ortholite insole which also made picking them up that much easier. The break in time was minimal! 3-5 wears to feel broken in max.

What makes them so comfortable and wearable in your opinion?: The comfort comes from the shape of the toe box (round and spacious) as well as the insole. They also feature a lightweight vibram outsole and Danner’s Dry weather seal to keep your foot dry in the rain.

Name: Candace Reels

Title/profession: Content Creator ( Fashion/Lifestyle )

Handle: @candacereels

Brand: Jeffrey Campbell

Model: Sherpal Bootie

What compelled you to buy?: So I’m one of those weird people that likes to go to the mall two days before Christmas just for fun vibes and to be amongst the chaos. So I’m at Nordstroms with my mom and I see these beautiful burgundy square toe booties. I immediately needed to try them on! I didn’t have anything like these shoes in my closet. And a couple days before that I saw a woman with the same beautiful square toe booties at Capri Club and made a note in my mind that I needed shoes just like that. So it was literally meant to be.

What kind of outfits does it pair well with/ badly with?: They pair well with literally all of my outfits. I’ve worn them with jorts, a suit, and dresses. If you look at my fits on Instagram, they are probably in every other post.

How long did they take to break in?: A couple of days. I went to Cincinnati to visit my fiance’s family after Christmas and it did not take long to break in at all. I was able to wear them all week and they gave me no issues. Since then I have worn them all around LA, London, Stockholm, Amsterdam, and Edinburgh.

What makes them so comfortable and wearable in your opinion?: There are a few reasons they are so comfortable. One of them is because they are square toe boots, my feet don’t feel squished in them. It has a good sturdy chunky heel, so you don’t feel off balance or like you’re going to fall. To me these boots are very versatile, they can be worn day or night, with dresses or suits, if you want to dress up or dress down. They are the perfect boot in my opinion.

Name: Jake Woolf

Title/profession: pro content guy

Handle: @jakewoolf

Brand: Aurora Shoe Company

Model: Middle English

What compelled you to buy?: I saw every store carried them and everyone I respect had a pair—I figured they couldn’t all be wrong.

What kind of outfits does it pair well with/ badly with?: these pair best with chill baggy jeans and pants. I like an elastic waist pant with a wide leg opening like this moleskin pair from Comoli or just regular sweatpants. They would look bad with slim pants IMO as their blob form is just too, well, blobby against something tailored.

How long did they take to break in?: about two weeks. I was a little concerned for a few days that the right shoe was too small, but I powered through and eventually they gave in. I also put on two pairs of socks and took a hot hair dryer to them to give them a little break in boost which worked like a charm. Now they’re perfect.

What makes them so comfortable and wearable in your opinion?: they’re literally designed with no shape so that they take the form of your foot over time. That’s great for me because I have weirdly shaped feet. That logic applies to the upper but they’ve also got a leather insole that patinas and molds to your toes and arch. Combine that with a lightweight Vibram sole (re-soleable btw!) and you’ve got a pair of shoes that I personally see being my kick on go-tos for years to come.

Name: Danny On

Title/profession: Corporate Schmuck

Handle: @goodchineseson

Brand: Comme des Garcons Homme Deux x Dr Martens

Model: 1461

What compelled you to buy?: I was looking to buy my first pair of Dr Martens but wanted something a little more special...

What kind of outfits does it pair well with/ badly with?: All kinds! I’ve worn these with shorts, jeans, casual, and dressed up looks.

How long did they take to break in?: These were pretty comfy from the get-go. Oddly enough I did not experience the hellish break in period that most Dr Martens wearers experience.

What makes them so comfortable and wearable in your opinion?: They’re a classic derby style that fit seamlessly into my wardrobe. They’ve held up beautifully for the last 6 years and remain my comfiest pair of shoes.

Thanks to all my lovely friends for participating!