What should I wear today? Here are a few foolproof ideas

Let’s be honest: we've all found ourselves asking, 'what should I wear today?' at some point. But it doesn’t have to be difficult. With a few killer combos up your sleeve – from minimalist outfits to the rugged classics – looking put-together becomes second nature. Think of this article as your secret style playbook, loaded with timeless, go-to looks that work every single time. We’re talking those no-brainer outfits that take the guesswork out of getting dressed, so you don’t end up standing in front of your wardrobe, questioning life choices.

Whether you’re off to a casual hangout or something a little fancier, this cheat sheet will have you sorted, keeping you one step ahead on the style front without even breaking a sweat. So, next time you find yourself pondering what you should wear today, simply pull this out and pick a look.

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White T-shirt and olive pants

So, what should you wear today? Well, a classic white T-shirt and olive pants combo is always a good place to start. It might sound simple, but it hits that effortless style mark like nothing else. The crisp white tee brings a fresh, clean vibe, while olive pants add just the right amount of subtle colour – an earthy contrast that keeps things grounded. This duo works because it’s simple but visually balanced, with a hint of military-inspired cool. Add white sneakers for a classic finish, or try some brown loafers if you’re feeling a bit fancy. Whether you tuck in the tee or let it hang loose, this look never feels overdone.

Chambray shirt and white jeans

Chambray and white jeans are that rare pairing that feels polished without trying too hard. The chambray shirt’s lightweight, denim-like texture pops against the fresh white jeans, creating a high-contrast look that’s somehow rugged and refined at the same time. This white-jeans combo is perfect for sunnier days. Add some leather boat shoes or loafers for a nod to summer, or throw on low-top sneakers if you’re keeping it casual. And if it’s a bit chilly, a brown or olive jacket over the top seals the deal, pulling everything together while keeping that laid-back, effortlessly cool feel.

Breton top and jeans

A Breton top and jeans combo is a classic that’s hard to beat. The navy-and-white stripes give a bit of Parisian flair, while jeans ground it with that familiar, all-purpose style we all know and love. This pairing works because it’s comfortable yet polished, casual yet stylish – like a ticket to the French Riviera without the airfare. Try it with dark jeans and white sneakers for a crisp look, or go with faded denim for a more relaxed feel. And if you’re layering, a casual blazer or a lightweight bomber jacket keeps it sharp without overcomplicating things.

Black leather jacket and white T-shirt

The black leather jacket and white T-shirt look is a certified icon of cool, and there’s a reason it’s never gone out of style. The leather jacket brings just enough edge, while the white tee keeps things clean and easygoing. This combo practically begs to be paired with dark jeans and black boots, but don’t shy away from white sneakers if you want a lighter feel. The contrast between the tough jacket and crisp T-shirt just works, and with this look, you’ll feel ready for anything from a concert to a night out.

Flannel shirt and raw denim

Flannel and raw denim go together like coffee and early mornings – they just make sense. The flannel shirt’s cosy texture and classic plaid add a rugged touch, while raw denim keeps the outfit grounded and effortlessly cool. These two pieces are the building blocks of a laid-back, outdoorsy, workwear-inspired look that doesn’t feel contrived. Go with brown boots to complete the outfit, or swap in sneakers if you want to mix things up. Either way, this outfit ages well, especially as the denim and flannel take on character with each wear.

Unstructured blazer and jeans

The unstructured blazer and jeans combo is for those days when you want to look sharp but not overly formal. The relaxed blazer adds just enough structure, while jeans keep the vibe casual and approachable. A plain white t-shirt or an Oxford shirt underneath works perfectly, giving the outfit a bit of polish without veering into “business meeting” territory. Pair with loafers or clean white sneakers, depending on the occasion, and you’ve got a look that’s effortlessly smart without trying to impress anyone. It’s confidence in an outfit.

Overshirt and tailored pants

An overshirt with tailored pants is that perfect middle ground between casual and put-together. The overshirt – think of it as a lightweight jacket with a bit more structure – keeps things relaxed, while tailored pants give just enough refinement to keep it sharp. Choose a neutral or earthy colour for the overshirt, like olive or beige, and pair it with darker trousers for contrast. Throw on some leather sneakers or loafers, and you’re ready for anything the day throws at you. This look is ideal for those in-between occasions when you need to look polished without overdoing it.

Camp-collar shirt and linen pants

A camp-collar shirt and linen pants are as close to a holiday vibe as you can get without leaving town. The open collar on the shirt adds a touch of personality, while the linen pants keep things breezy and relaxed. This outfit is built for summer days and outdoor brunches, with espadrilles or loafers completing the look. Go for light, earthy tones to keep the vibe natural and laid-back. It’s comfortable, stylish, and just the right amount of “vacation mode” without looking like you’re trying too hard.

Wool overcoat and chunky knit

A wool overcoat and a chunky knit is a cold-weather combo that doesn’t mess around. The overcoat brings sophistication, while the chunky knit adds a layer of warmth and texture that just feels right when temperatures drop. Choose a neutral-toned overcoat, like camel or charcoal, and throw it over a navy or forest green knit for a look that’s both practical and polished. Add dark jeans and boots, and you’re set. This is the outfit that says “winter-ready” without sacrificing style.

Oxford shirt and chinos

What should you wear today? Well, a classic Oxford shirt and chinos combo is always a good option. The Oxford brings a touch of structure, while the chinos keep things comfortable and versatile. Go for a light blue shirt and beige or olive chinos for a classic look, and roll up the sleeves if you’re feeling relaxed. Loafers or white sneakers finish this outfit perfectly, giving you a no-fuss, clean look that’s ready for almost anything. This pairing has that timeless appeal – you’ll look great without looking like you’re trying.

Next up: A few winter-specific outfit suggestions.

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