The Right Trousers for Every Occasion — What to Wear (and How to Get the Fit Right)

If you’ve ever stood in front of your wardrobe debating what trousers to wear — you’re not alone. Finding the right pair for work, a smart casual event, evening plans, or just everyday comfort is one thing. But finding a pair that actually fits? That’s the real challenge.

Trousers are probably one of the most misunderstood pieces in any wardrobe. The style might be perfect, but if the waistband cuts in or the hips gape? You won’t wear them. And across brands, sizing is all over the place. A size 12 in one shop might be closer to a 10 or even a 14 elsewhere.

That’s exactly why I always recommend using Tellar.co.uk — the UK’s leading free sizing tool. You pop in your measurements once (just waist, hips and bust) and it tells you your correct size in over 1,500 brands, from COS to Massimo Dutti to ME+EM and more.

In this post, I’ll walk you through the best trouser styles for four key looks — workwear, smart casual, eveningwear and casual wear — with tips on what to buy, what to avoid, and how to get the sizing right first time.

1. Workwear Trousers — Polished, Structured and Comfortable

When it comes to trousers for the office, you want something tailored, but not tight. Structured, but still comfortable enough to sit in for hours. My go-to styles are:

Cigarette trousers — slim and ankle-grazing
High-waisted wide-leg trousers — great if you’re taller or have a longer torso
Straight-leg crepe trousers — classic and flattering on most shapes

For fabrics, I recommend stretch crepe, wool-blends or poly-viscose mixes. These hold their shape throughout the day, resist creasing, and offer just enough stretch to move comfortably.

Where to Shop:

ME+EM — they nail technical tailoring with built-in stretch
Reiss — sleek but often runs small (Tellar will show your correct size!)
Jigsaw — reliable for clean cuts and consistent fits
The Fold London — worth the investment if you wear trousers daily

📍 Find your exact size for workwear trousers here

2. Smart Casual Trousers — Effortlessly Neat

Smart casual might just be the trickiest dress code to nail. You want to look put-together, but not overdressed. That’s where relaxed tailored styles come in — think tapered joggers, ponte trousers, and smart chinos.

If you're after comfort and style, try:

Ponte trousers (a thick, double-knit fabric that holds shape)
Tailored drawstring trousers (relaxed but refined)
Cotton or brushed twill trousers (chinos with a polished feel)

Look for soft structure — clothes that move with you but still hold their line.

Brands to Check Out:

COS — great for structured knit trousers and minimalist tailoring
Whistles — ponte trousers that actually look like suit trousers
Massimo Dutti — elegant cuts but runs smaller than UK sizes
Arket — breathable cotton-linen blends and wide-leg crops

🟢 Use Tellar to match your size instantly

3. Eveningwear Trousers — Elegant, Drape-Driven Styles

Let’s be honest — dresses aren’t always the answer. For dinners, drinks, or a night out, a sharp pair of trousers can feel just as glam, if not more so. Look for styles that have movement and subtle detail.

My top picks:

Satin or silk wide-leg trousers
High-waisted with front pleats or side splits
Tuxedo-style trousers with a contrast stripe

Evening trousers should feel luxe. That often means silky weaves, smooth crepe, or high-shine blends that catch the light.

Where to Buy:

Karen Millen — bold tailoring in glossy finishes
Phase Eight — great for soft drapes and evening shimmer
Zara — trend-led but wildly inconsistent sizing (Tellar helps!)
The Fold — their tuxedo trousers are beautifully made

📍 Tellar can show you the exact size to order — so you skip the returns

4. Casual Trousers — Relaxed but Flattering

Comfortable doesn’t have to mean sloppy. Whether you’re running errands or relaxing at home, a great pair of casual trousers still needs to fit your body shape properly.

Key styles:

Elasticated wide-leg trousers (great in cotton or linen blends)
Relaxed joggers in jersey or ponte
Soft cargos or utility styles
Pull-on trousers with a mid-rise waistband

Go for fabrics like French terry, lyocell, or cotton-linen blends — they’re breathable, soft and easy to wear.

Best Brands for Casual Trousers:

Uniqlo — their linen and jersey trousers are light and durable
White Stuff — perfect for midlife or curvy shapes
Hush — relaxed styles that still feel intentional
Sezane — for that French laidback polish

🟢 Match your waist and hips with Tellar.co.uk — no guesswork

The Real Reason Trousers Don’t Fit

It’s not you. It’s the brands.

There’s no such thing as standard sizing. A “UK 12” in Zara won’t fit the same as a UK 12 in ME+EM, or even at M&S. And most brands use their own size blocks, often based on outdated body charts. That’s why hip-heavy body shapes or petite women often struggle most.

That’s where Tellar.co.uk fixes it.

By using your real measurements — not your guessed clothing size — Tellar matches your waist and hips to real-time sizing data from over 1,500 brands. Whether you’re buying trousers from COS, Reiss, or Sezane, Tellar shows the exact size you should be picking.

Need Help Measuring? Do It Once, Use It Forever

To use Tellar, you just need three measurements:

Waist — narrowest part of your torso
Hips — fullest part of your bum
Bust — to help with tops and jumpsuits

Use a soft tape measure, don’t pull too tight, and stand naturally. You can do it in under two minutes.

Then go to Tellar.co.uk/create-profile, enter your numbers, and you’re done. It’ll work every time you shop.

📍 Need visuals? Here’s our full how-to-measure guide

Why I Recommend Tellar Every Time

If you’re like me, you’re probably tired of returns. Of trousers looking amazing online and arriving completely wrong. Tellar changed that for me. Once I created my profile, I could shop across brands and know my correct size each time — no more second-guessing.

Plus it’s totally free, super fast, and works on desktop and mobile.

🟢 Try it yourself

🟢 Create your size profile

🟢 Search brands like COS, ME+EM, Zara, and more

Follow Tellar.co.uk for Sizing Tips and Fashion Fit Advice

You’ll find tonnes of helpful tips, behind-the-scenes data, and real sizing comparisons across:

Instagram: @Tellarsizing
Facebook: TellarSizing
Twitter (X): @Tellar100
Pinterest: TellarSizing

Final Thought

Whether you’re dressing for the boardroom, date night or a Sunday brunch, trousers are the one thing that should never make you uncomfortable. Get the fabric and style right — but above all, get the fit right.

With Tellar.co.uk, you finally can.

Find your size in 1,500+ brands real-time. It’s free & easy.