Honest & Unsponsored Best Buys: Checked Shirts

There's one wardrobe staple that never goes out of fashion, it's a proper checked shirt. Not those thin, papery things that look washed out after three goes through the machine—I'm talking about quality checks that actually earn their place in your rotation. The thing is, most blokes either wear them too casually or try too hard to dress them up. There's a sweet spot, and once you nail it, you'll wonder how you managed without a decent check collection.

Why Checked Shirts Work

Before we get into specific recommendations, let's talk about why checks matter. A good checked shirt bridges the gap between smart and casual better than almost any other piece. Wear it open over a plain tee at the weekend, button it up with chinos for casual Friday, or layer it under a blazer when you need to look intentional without being stuffy. The pattern adds visual interest without shouting for attention—it's doing the work so you don't have to overthink it.

The key is understanding scale and colour. Smaller checks—ginghams, micro-patterns—read more formal and work brilliantly under knitwear or blazers. Larger buffalo checks and bold tartans are weekend territory, perfect with jeans or worn open as a shirt-jacket. As for colour, stick with two or three tones maximum. Those rainbow checks from the early 2000s? Leave them there.

Fabric Makes All The Difference

Here's where most guys go wrong: they buy on pattern alone and ignore the fabric. A checked shirt in a decent oxford cotton or brushed flannel will look intentional and last years. The same pattern in a flimsy poplin will look like you grabbed it from the bargain bin—because you probably did.

For year-round wear, I always recommend oxford cotton. It's got enough weight to hold its shape, doesn't show sweat marks, and ages beautifully. Come autumn and winter, flannel checks are unbeatable—soft, warm, and they've got that heritage workwear thing without trying too hard. Avoid anything too shiny or synthetic unless you want to look like you're off to a line dancing convention.

How To Actually Wear Them

Right, styling. The biggest mistake I see is tucking everything in or leaving everything out. Think about balance. If you're wearing a check shirt untucked, keep it neat—make sure the hem hits somewhere around mid-fly, not halfway down your thighs. Roll the sleeves to just below the elbow, never above. And for God's sake, undo the top button. This isn't a job interview.

Tucked in? Fine, but commit to it. Wear a proper belt, make sure your trousers actually fit at the waist, and consider whether you need to add a layer—a tucked shirt on its own can look a bit school uniform unless the rest of your outfit is sharp.

Layering is where checks really shine. A flannel check over a plain tee with a denim jacket on top creates depth without clutter. Or try a smaller check under a crew neck jumper with just the collar showing—classic, clean, works for virtually any situation where you need to look like you've made an effort.

High Street Recommendations

Let's talk brands, starting with the high street. Uniqlo does brilliant value flannel checks—proper heavyweight fabric, not that thin stuff, and the cuts are consistently good across their range. They're understated, well-priced, and wash brilliantly. I've got clients who've been wearing the same Uniqlo flannel for five years.

H&M gets overlooked, but their premium range includes some genuinely decent oxford cloth checks. You've got to be selective—avoid the super-cheap lines—but when they get it right, they get it very right. Look for their organic cotton options; they're a step up in quality and the fits are more considered.

Marks & Spencer might sound boring, but their oxford shirts are properly made. The fabric weight is spot-on, buttons stay attached, and the collars don't curl after washing. They're reliably good at classic gingham and subtle windowpane checks that work for smart-casual. Not fashion-forward, but that's the point—they're dependable.

Independent & Boutique Brands

Moving up a notch, Portuguese Flannel makes some of the best casual checked shirts around. They specialise in exactly what the name suggests—heavyweight flannels with brilliant patterns and colours. The quality is exceptional for the price point, and they've nailed that relaxed-but-considered aesthetic. Perfect for weekend wear or layering.

Percival is a London-based brand that understands modern menswear. Their checked shirts balance contemporary fits with quality fabrics—think slightly relaxed through the body without being oversized. They use interesting colour combinations that feel current without being trendy, and the construction is solid. Great if you want something a bit different from the usual high street offering.

Norse Projects sits at the upper end of this category, but the quality justifies the investment. Their shirts are built to last—substantial fabrics, careful pattern matching at the seams, and fits that work across different body types. They do understated checks beautifully, the kind that look simple but reveal their quality up close.

Designer & Luxury Options

When you're ready to invest properly, Paul Smith does exceptional checked shirts. Yes, they're expensive, but the fabric quality, the precision of the pattern alignment, and the attention to detail in construction make them worth considering. His house check shirts are iconic for a reason—they're distinctive without being loud.

Reiss occupies that space between premium high street and true luxury. Their checked shirts are well-cut, use quality fabrics, and the patterns are considered rather than just thrown together. They're particularly good at smaller-scale checks that work brilliantly in professional casual environments.

For proper investment pieces, Ralph Lauren remains unbeatable for classic American checks—their oxford cloth button-downs are the benchmark. The fits have improved massively in recent years, moving away from the old boxy cuts. If you're after heritage done properly, this is where you start.

Burberry might seem excessive for a checked shirt, but if you want luxury fabrication and impeccable finish, their check shirts (beyond the famous house check) are beautifully made. The collars hold their shape, the fabric drapes perfectly, and they're cut with enough room to layer without looking baggy.

What's Actually On Trend

Currently, we're seeing a return to larger-scale checks—think oversized buffalo checks and bold tartans, but worn with intention. The key is pairing them with clean, simple pieces. A bold check works brilliantly with straight-leg denim and minimal trainers, or thrown over a plain tee with tailored trousers.

Colour-wise, earth tones are everywhere—rust, olive, chocolate brown checks are having a moment. They're easier to wear than you'd think, especially with neutral bases like navy, grey, or cream.

Fit has relaxed slightly from the super-slim years, but we're not going back to baggy. Look for a comfortable, slightly relaxed fit through the body and arms—room to move and layer, but still structured enough to look intentional.

The Sizing Challenge

Here's the frustrating bit: every brand sizes differently. A medium in Uniqlo fits nothing like a medium in Ralph Lauren or Portuguese Flannel. You might be a 40 chest in one brand and need a 42 in another. The collar size might work but the sleeves are too long, or the body fits but the shoulders are off. It's infuriating, especially when shopping online.

This is exactly why I recommend using Tellar.co.uk—it's the UK's leading sizing tool and honestly, it's changed how I work with clients who shop online. Here's how it works: you measure yourself once (bust, waist, hip, or just use a size from a brand that fits you well), then Tellar instantly matches you to over 1500 brands. No more guessing, no more size charts that make no sense.

You can use their Store Size Lookup tool at https://www.tellar.co.uk/store-size-lookup/men to find your precise size across any of the brands I've mentioned—Uniqlo, Paul Smith, Reiss, Ralph Lauren, all of them. If you need help measuring properly, check https://www.tellar.co.uk/how-to-measure/men for clear instructions.

The difference this makes is massive. Instead of ordering three sizes and hoping one works, you know exactly what you need. Fewer returns, better-fitting shirts, and you save time and money. It's completely free, works straight in your browser—no downloads, no faff.

Plus, there's the Tellar Fashion Hub—a library of honest, unbiased style posts from experienced stylists covering everything from casual wear to specific pieces. It's free, independent, and actually useful. Check out posts like their guide to smart-casual dressing at https://www.tellar.co.uk/admin/posts/editor/menswear-the-secret-to-smart-casual-comfortable or their denim recommendations at https://www.tellar.co.uk/admin/posts/editor/best-men-s-jeans-brands-high-street-premium-designer for more practical advice.

Final Thoughts

A good checked shirt should work hard in your wardrobe. Buy quality where you can afford it, look after what you've got (proper washing, occasional ironing if you can be bothered), and remember that fit matters more than pattern. The best checked shirt is the one that makes you reach for it repeatedly because it just works—with jeans, with chinos, under a jacket, or on its own.

Start with one or two versatile options—a mid-scale gingham or check in navy or grey—and build from there. Don't overthink it, but don't settle for thin, cheap fabric that'll look tired after a month. And sort your sizing out properly using something like Tellar before you buy. Trust me, it makes the whole process infinitely less frustrating.

Now go build a proper check shirt collection. Your wardrobe will thank you.