With flashy discounts and the creeping fear that comes when there’s only one left in your size, it’s all too easy to walk away from sale shopping with impractical, ill-fitting or just plain unwearable clothes.

But done right, a sale is a fine opportunity to stock up on essentials and indulge in big-ticket items without dropping a wedge. Which is why we’ve teamed up with Reiss for the launch of the premium high street brand’s up to 50 per cent off sale.

It’s the early bird who catches the half-price leather jacket, as they say, so to help you get ahead we’ve picked out the 16 best items you can wear now and well into the new decade.

Ronnie Leather Trucker Jacket

Finding the perfect leather jacket is a lot like dating (hear us out). There are plenty of bad fits out there, but a few taps of a screen can help you find ‘the one’ in no time at all. The Ronnie trucker is buttery soft with clean, contemporary styling that transcends seasons. Wear it now over a roll neck and flannel trousers, then with a white tee and jeans in the spring.

Buy Now: £350 £225

Zingara Brushed Trousers

We’re going to let you in on a secret to dressing well. Get yourself a pair of grey trousers that can do it all: smart, casual, that weird bit in between. Reiss’ Zingara pair are cut slim and made from textured sharkskin wool that wears well and is resistant to creasing. Dress them up with a navy blazer and brogues, or down with a sweatshirt and trainers.

Buy Now: £115 £55

Sacro Wool-Blend Peacoat

Of all military classics, the peacoat is arguably one of the most versatile. It goes just as well with a fisherman knit and jeans for weekends down the pub as it does with a shirt and tie for smarter settings. The Sacro’s wide lapel and double-breasted cut help it swing both ways. Just pop the collar, and you’re good to go.

Buy Now: £295 £225

Barton Zip-Neck Polo Shirt

Wardrobe classics don’t have to be boring. In fact, the smallest details can make a massive difference. Take the Barton polo shirt. A zip-through fastening takes it from menswear staple to futuristic and vibey, while the short sleeves and slim fit add to the sporty feel. Wear it with cropped black trousers and chunky trainers, adding an unstructured suit jacket when the occasion calls.

Buy Now: £65 £50

Woking Double-Breasted Wool Blazer

Double-breasted jackets have always been popular in well-heeled circles like the City. But in recent years the rest of us have clocked on to their potential too, making them the tailoring trend to beat right now. Jackets like the Woking – with a wide lapel and nipped-in waist – are elegant but modern, especially when worn with a crew neck jumper or T-shirt.

Buy Now: £325 £225

Bless Crew Neck T-shirt

Admittedly, it’s a bit nippy to head outside in just a T-shirt right now. Still, the Bless crew neck’s winter-ready colour palette makes it ideal for layering underneath a suede jacket. The rust hue is also universally flattering and goes with just about anything, so it won’t be left out in the cold.

Buy Now: £25 £15

Liam Leather Trainers

As we roll into the new decade, sneakers are moving away from the ‘ugly’ runners of the past year or so and towards something slightly more refined. The Liam combines retro marathon styling with clean lines and premium materials. Wear them with tailored trousers and a bomber jacket, just keep an eye out for puddles.

Buy Now: £185 £85

Bishop Bifold Card Wallet

If sales season has given your wallet a bit of a battering, why not replace it with a fresh one for the new year? The Bishop is a pebbled leather bifold that has ample space for notes, cards and coins, but is streamlined enough to sit in the slimmest of trouser pockets without calling attention to itself.

Buy Now: £55 £40

Bronson Block Knit Jumper

It used to be a choice between a smart wool jumper and interesting graphic sweatshirt. Now, the lines are blurring. Reiss’ Bronson jumper is spun from a wool-cotton blend with classic ribbing and a geometric motif up and down the body. Got a camel coat hanging in the wardrobe? Throw it over this for a cool tonal look.

Buy Now: £130 £65

Lasoo Washed Jeans

Given the number of alternatives out there these days, it would be easy to overlook denim. And yet, there’s nothing quite like a pair of well-fitting jeans. The Lasoo model features a classic slim fit with a hint of stretch and a subtle black wash. Wear them with everything – cosy boy mohair jumpers, smart button-down shirts, technical jackets. Seriously, everything.

Buy Now: £115 £65

Kennard Dogtooth Overcoat

You shouldn’t need to look at a thermometer to know ‘tis the season to invest in an overcoat. You’ll want one that can be thrown over everything from a hoodie and joggers to corporate office-wear. Enter the Kennard, crafted from a fuzzy wool blend in a handsome dogtooth pattern, it will add textural interest to pretty much any ‘fit.

Buy Now: £295 £160

Jinks Wool-Cashmere Blend Jumper

Sale season is a prime opportunity to upgrade your essentials with slightly better fabrics, like switching out your tired jumpers for something in a soft cashmere blend. The Jinks, a simple crew neck with exposed seam detailing, is a true all-rounder that will still be trucking this time next year.

Buy Now: £95 £45

Bronmann Leather Trim Backpack

Bum bags and chest rigs might be having a moment right now, but let’s be honest – they’re not always the most practical option. Much better is a smart backpack big enough for your laptop, gym kit and whatever else you might need to throw in there. The Bronmann comes with a pure grain leather trim, putting it a notch above the rest.

Buy Now: £195 £110

Jake Scotchgrain Leather Monk Strap Shoes

There’s no such thing as good, cheap shoes. The simple fact is, you always get what you pay for. The Jake monk straps are crafted from supple scotchgrain leather in a eye-catching bordeaux colourway, making them ideal for winter weddings, summer weddings, basically any time where you want to make a little extra effort.

Buy Now: £245 £120

Melrosen Brushed Cotton Twill Shirt

The easiest way to get the most out of sale shopping is to avoid anything trend-led. Instead, stick to versatile classics that will last longer than a single season. The Melrosen, for example, is cut like a regular shirt but from soft brushed cotton, helping it to strike a good balance between office-ready and weekend-fancy.

Buy Now: £110 £60

Rivet Wool-Blend Bomber Jacket

If you look up ‘wardrobe investments’ in the dictionary, you’ll likely find an image of the Rivet jacket. Made from a wool-blend and finished with a detachable faux-shearling collar, it’s both warm and insanely soft. The silver hardware gives the casual mid-weight style a sleek edge, meaning it can be used to pep up even the most casual of looks.

Buy Now: £275 £170