Loafers, redefined: from daywear to evening
More than footwear — loafers are versatile essentials combining comfort, elegance and ease, from relaxed lunches to late dinners.
TrustScore 4.9 | 12,143 reviews
Winter Fit 5 - Aspen Day
£146.91
£367.09
SAVE £220.18
WINTER SALE: UP TO 50% OFF + FREE UK DELIVERY
Limited seasonal stock — once it’s gone, it’s gone. Order today for fast, tracked delivery across the United Kingdom.
View offer details →Shop the Winter Look: Aspen Day
Handpicked by our team & discounted with a special outfit bundle price.
Embrace timeless elegance with our "Shop the Look" outfit, perfect for an afternoon stroll. This curated ensemble combines comfort and style, ensuring you stand out in any coastal setting.
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100% Merino Wool Zip Up - Gray: Crafted from 100% high-quality garments, this top offers unparalleled comfort and sophistication.
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Polarised Old Money Sunglasses - Transparent These sunglasses will give you a mysterious & classy look and perfectly match with the gray zip up.
- Old Money Suede Loafers - Beige: These versatile loafers blend comfort with elegance, perfect for transitioning from the beach to a sunset dinner.
Every order is shipped quickly and securely with tracking across the United Kingdom — so you can shop with total confidence.
If something isn’t quite right, our 30-day hassle-free returns policy makes it simple to arrange an exchange or refund.
Our pieces are made using carefully selected premium fabrics, finished with attention to detail and a focus on lasting quality.
Through precise craftsmanship, each garment brings together comfort, structure and durability — refined, modern and timeless.
Shop with confidence — we stand behind every piece. At CHESTERFIELD, it’s about more than style: it’s about timeless quality, reliable service and pieces that elevate your everyday.
Each item reflects our modern take on classic British elegance — designed for comfort, longevity and effortless refinement.
Winter Fit 5 - Aspen Day
Sale price£146.91
Regular price£367.09
4.9
out of 5
Based on 12,143 reviews
37 minutes ago
Quality that stands out
You can tell straight away these are made properly — clean finishing, solid stitching and a premium feel. They look even better on foot.
1 hour ago
Comfortable from day one
No break-in needed. Wore them around London all day and my feet felt great — supportive and soft inside, without rubbing at the heel.
2 hours ago
Perfect down to the details
The detailing is spot on — you can see the care in the finish. The sole feels solid and the overall build feels premium, not flimsy.
3 hours ago
True to size
I’m usually unsure ordering trainers online, but these fit true to size. Snug in the right places and comfortable around the toe box.
1 day ago
Easy order, quick delivery
Smooth checkout and the delivery was on time. They arrived well packaged and looked exactly like the photos — really impressed.
2 days ago
Still looks new
After a good few wears they still look fresh. The materials hold up well and the sole hasn’t softened or lost grip.
1 week ago
Instant confidence boost
They elevate any outfit. Clean, sporty and premium — you feel put together the moment you lace them up. Loads of compliments.
2 weeks ago
Lightweight but supportive
Exactly what I wanted — lightweight on foot but still supportive. Great for day-to-day wear and travelling.
3 weeks ago
Easy to style
Smart-casual or relaxed — they always work. They look premium with jeans and clean with joggers. Proper versatile pair.
1 month ago
Great grip in wet weather
Tried them in rainy UK weather and the grip is genuinely good. The sole feels stable and secure on pavements.
2 months ago
First order — now my daily pair
Took a chance and I’m glad I did. They’re now my daily trainers — comfortable, stylish and they still look premium after weeks.
3 months ago
Customer service was excellent
Had a quick question about sizing and got a helpful reply straight away. The whole experience felt premium from start to finish.
THE CHESTERFIELD COMMUNITY
With over 50,000 satisfied customers across the United Kingdom, the CHESTERFIELD community continues to grow — defined by timeless style, premium quality and genuine passion.
LOAFERS
Soho Espadrilles
Sale price£60.73
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THE CHESTERFIELD EDIT
Your compact guide to modern menswear, essential staples, and effortless refinement — the British way.
Linen done properly: why it belongs in every wardrobe
Refinement with ease. Worn well, linen adds texture and structure — perfect for elevating everyday looks effortlessly.
Wardrobe foundations: build a collection that lasts
Quality over quantity — invest in versatile, well-made staples. With the right core pieces, getting dressed becomes effortless.
The finishing touch: mastering accessories
Details make the man. A refined watch, the right belt, or a sharp loafer turns any outfit into a considered look — understated, yet unmistakable.