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 57 reviews
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.
I’ve had these shoes for over a year, and I’m still very happy with them. I’m quite demanding when it comes to shoes, but these immediately felt different. The quality is outstanding, the leather feels premium and the shoes are built to last.
What I like most is that they combine the look of a stylish sneaker with the comfort and support of a much more substantial shoe. They feel solid, supportive and comfortable all day long. Even after a year of wear, they still look great and feel just as good.
A fantastic purchase and easily one of the best pairs of shoes I’ve owned.
I've had my Chieftains for a little over a year now, and I'm so happy with them that I've ordered a second pair. I wore them regularly through the winter and I'm usually pretty tough on my shoes, so very impressed that they're still going strong with only minor wear on the soles. The waxed leather is robust and requires little maintenance beyond brushing. They're smart enough to wear to the office, comfy enough to walk around in all day and look good with everything, really can't fault them.
This is a solid, well constructed shoe. The welting is perfect and the materials used are high quality. I found the footbed comfortable out of the box. Considering the weight of the leather, the break-in time was minimal. The color is great. This is not a lightweight pair of shoes.
When I first took them out of the box, I thought “Oh, these look solid!” Straight away they gave me a good impression.
I really like the design. It’s simple and clean, but not plain. They look good with jeans or chinos, super versatile.
The leather feels great — soft but with enough firmness, and the color has a nice rich depth to it. After trying tons of different shoes in Japan, these definitely feel like really good quality for the price. The construction is sturdy, they’re comfortable right from the first wear, and overall the whole package (leather quality, comfort, and even the brand’s story) is impressive.
Honestly, the cost-performance is excellent. They feel like shoes that will last a long time without breaking the bank. I’m very satisfied!
Bought the Riders on a small tradefair in Düsseldorf, Germany. Great guy, great boots. Have to be broke in until they are really comfortable. The contrast of the grey suede and brown soles is awesome.
During the unboxing the amazing quality and eye for detail stood out! I ordered my pair one size too large, and a different pair was quickly arranged with Robin. Absolutely amazing customer service.
Shoes have a great fit. Bit stiff at first and you have to wear them in, but then… heaven!
First time buying a high quality sneaker.
We went to the physical store in Gent. The reception and information given about the shoes and how they were made was really great. It's the first time that I'm actually purchasing a high quality sneaker (and shoe in general really). They are really easy to use and fit like a glove. You can also see that the materials used are of high quality. They are a match for all outfits!