Break-in Guide for your New Shoes
New (quality) shoes can feel stiff at first, but don't worry—this is part of the journey. Here are a couple of tips to break them in:
1. Start slow
Wear them at home for short sessions (1–2 hours). Increase gradually over a few days. Avoid full workdays or long walks during the first wears. You'll give the materials time to become more supple and set/shape to your feet.
2. Thicker socks help
They add a bit of cushioning while the leather softens and the soles become more flexible.
3. For lace-up boots:
Skip the top lacing hook for the first few wears, or use the tie-around method. This prevents the top edge from pressing your leg until the leather relaxes.
4. Heel slip:
Mild heel slip is normal in the beginning — especially with Goodyear welted shoes. The soles are sturdy and not yet flexible at the toe joint, which creates a bit of tension and leveraging movement at the heel. Once the soles start to break in and flex naturally, heel slip will diminish.
*Remember*
Quality shoes are often less comfortable at first — they become comfortable through wear, as the materials gradually soften and shape to your feet.
Real reviews from real customers
Let customers speak for us
from 88 reviews
Really pleased with my purchase, excellent quality, the boots are comfortable right out of the box.
I have sightly wider feet and I didn't have any issues with them.
I have the Walnut Brown version and absolutely love them. The leather is spot on and they are very well-made. The removable Kilties and tassels are genius and offer a lot of options to play with the appaearance. I followed the sizing advise and they fit very well.
I like the loafer very much. The quality is outstanding, just like my other shoes from the company. I followed the advice and ordered them half a size smaller.
I had to wear them a few times in order to wear them in. After having done this they are very comfortable. I am sure they will last a long time. The prize is justified for what you get.
I can recommend this shoe. I also like the opportunity to change the appearance with the available accessories. That’s a great idea
The Kudu leather is absolutely breathtaking. This is my first pair of Chieftains, and let me tell you, the fit is amazing. The finishing touches are spot on, and the color is easily one of the most versatile boot tones out there because it shifts between taupe, olive, and a grey-navy mix depending on the lighting and what pants you wear. It is just such an incredible boot. Regarding the fit, the size is exactly the same as most of my other boots like Red Wing, which is one full size down from my standard sneakers by Nike or Adidas. I will certainly be buying another pair from Lennertson in the future.
Though classic in style, they are also quite contemporary in the way they are brought.
They definitely don't look like an old pair, and don't make you feel or old-fashioned .
The beautiful grain of the leather, the modern cut, the thick sturdy sole, and the fun little accessories make them really quite nice.
I love them !
I can easily wear them with both a casual outfit and a business suit. They add a distinctive sense of style and character to every look, something I don't often get from more traditional dress shoes. They did take a little time to break in, but once they did, they became incredibly comfortable. They've quickly become one of my favorite pairs of shoes.
Opened the box and boy was I happy, they are beautiful, I find them extremely comfortable and they are on a par with boots that cost a multiple of the price
The Brawler in my opinion is the perfect fit between a nice gentleman shoe and something a bit robust. Works great if you dress up a bit and also great underneath some jeans. That's why I have two pairs ✌️😁
when first wearing, the high rim was a bit rough and hard, but that got smoother after wearing for a while
so now, worn in, they are pretty perfect ! :
the leather is strong, it looks good, but above all the 'feel' is there: when walkng they give the stride a comfortabele, elegant and energetic feeling
always happy to put them on for the road
I went into their pop-up store in Ghent. The gentleman behind the counter took his time explaining all the design choices that went into making the shoe. After a one hour conversation (i was interested and also asked loads of questions) i tried on some shoes. They really do feel premium. At first i wanted to think some more about wether or not i wanted to buy the shoe, i went outside to grab a coffee but immediately returned to buy my first pair. Still my favourite pair to wear until this day!!
The Lennertson Brawler feels fantastic. From the moment you put it on, you feel more grounded, stable, and confident. It's one of those rare shoes that not only looks great but also changes how you feel—ready to take on the day with confidence. The craftsmanship and comfort are excellent, and the value for money is outstanding. You get a premium feel and quality without paying a premium price. Five stars. ⭐⭐⭐⭐⭐
I've been looking for a long time to get high quality boots, that also look "business casual. Used them during winter, they did not disappoint. They keep their color and shape very well. High quality leather, soles, ...
They do take some time to break in compared to boots made with less thick materials.
I've had my eye on a pair for a long time, specifically 'The Brawler'. After a lot of research and waiting, I finally bought them, and I honestly didn't expect the quality to be this high. What immediately stood out upon opening the box was the gorgeous color and shape. It truly is a case of 'what you see is what you get'. I'm absolutely thrilled with them, and now I've got my sights set on the black ones!
I’m a picky shoe buyer and have been very pleased with the three pair of Rider boots from Lennerston. The quality of the boots and the service from Lennerston were excellent.
Absolutely quality shoes. Even after wearing them for a full winter season they still looks great.