Thanks to the cyclical nature of men’s fashion, we’re often encouraged to think of style as fitting neatly in one of the four seasons. But, as anyone who has experienced life in a temperamental clime will know, what’s perfectly appropriate on one day becomes extremely ill-suited the next.

There is good news however. Chosen carefully, some of the very same pieces that have seen you through summer can be worn well into autumn too.

So, before you start plotting your new season wish list, reconsider the following five warm-weather staples, which work just as well from September onwards – provided you style them right.

1. The Breton Top/T-Shirt

Few menswear pieces are as synonymous with warmer weather as the Breton top. Its blue and white stripes have the ability to add an instant dose of effortless cool to an outfit (see James Dean for proof), and though designers and brands may produce subtly tweaked versions of this classic season after season, it’s hard to imagine a summer where the Breton top is absent from the menswear landscape.

That said, this is a garment which will bolster your personal style just as much during dark and dreary autumn/winter months as it does when the sun is shining.

Wear alone with chinos or under a navy blazer to nod to the garment’s Riviera appeal on those unexpectedly warm September days, or combine with classic black leather bomber and jeans for a downtime look spliced with timeless style.

If you’re looking to reference the Breton top’s heritage and keep the nautical vibe going well into the new season, try teaming with a hardy duffle or waterproof fisherman’s jacket, heavyweight twill chinos and a fitted beanie for a seasonally-appropriate ensemble that conjures images of dark nights spent (stylishly) at sea.

Men's Breton Striped Top Outfit Inspiration Lookbook

Mango Man 2015Selected Homme Jeans AW14Mango Man AW14Burberry Black Label SS15H&M Modern Essentials 2015UnknownZara AW15Acquascutum SS15El Burgues AW15

2. Leather Loafers

A brief glance down on any stylish city street this summer will reveal that leather loafers – be they penny or tasselled – have reasserted themselves as the shoe of choice for the most discerning dressers.

Thanks to their ability to look more polished than trainers and sandals, while still feeling informal enough to wear off-duty, they’re a summer footwear stalwart, and one that you needn’t pack away just yet.

In fact, it’s only relatively recently that the industry has positioned leather loafers as a go-to warm-weather silhouette. Based on a style of shoe historically worn by Norwegian fishermen, it’s no surprise that the design can be easily worn when temperatures tumble.

In early autumn (weather permitting) it’s still perfectly acceptable to bare your ankles for as long as you can withstand the encroaching cold. When off-duty, try wearing your loafers sockless with white jeans and your Breton top/tee, layering an overshirt on top if the forecast isn’t exactly auspicious.

Even better, your slip-ons will provide the perfect companion for autumn’s back-to-work tailoring. Brown or black leather designs worn without socks (i.e. with no-show socks) will add a nonchalant spin to a sharp Prince of Wales check suit or classic grey wool tailoring.

On colder days, don a pair of socks in a rich, seasonally-appropriate hue such as burgundy or bottle green to step into the next season with flair.

Men's Leather Loafers In Autumn/Winter Outfit Inspiration Lookbook

El Burgues AW15Boss Hugo Boss Pre-AW15MASSIMO DUTTI NYC AW15Charles Tyrwhitt 2015Mango Man AW14Gucci AW14J.Crew Casual 2015scotch & soda AMSTERDAMS BLAUW AW14Tommy Hilfiger Tailored AW14Zara November 2014Pull & Bear AW15The Tailoring Club AW15

3. The Floral Shirt

Forget everything you thought you knew about the floral shirt. Not only is it now a credible sartorial option for the summer (banish any thoughts of dodgy barbecue outfits), it will slot seamlessly into your wardrobe for next season too. What’s more, it provides one of the easiest ways to add a flash of pattern to your looks.

It may sound fairly obvious, but – as with styling the floral shirt in hot weather – the key to successfully introducing the design to your cold-weather rotation means letting the print take centre stage by combining with pared-back accompanying pieces.

Which items are the perfect companions for the floral shirt? When in doubt, stay neutral. For a contemporary take on the style, when wearing a suit, swap out your dress shirt and tie in favour of your punchy floral button-down, adding a pair of white trainers for a laid-back aesthetic that perfectly captures menswear’s new relaxed mood.

Remember, though, there’s no getting away from the fact that a floral shirt still packs plenty of clout; to keep your look eye-catching rather than offensive, consider sticking to darker, more muted designs that the industry has been pushing heavily this year.

Looking for a simpler way to wear the style? Toughen it up with a bomber/denim jacket, slim-fit jeans and a pair of Chelsea boots to instantly re-imagine your floral shirt for autumn.

Men's Floral Shirts In Autumn/Winter Outfit Inspiration Lookbook

River Island SS15Eton SS14Eleven Paris SS14Selected Homme 2013Burton SS14Mango Man SS15Massimo Dutti November 2014Reiss AW15Scotch & Soda SS15

4. The Chambray Shirt

In summer, the chambray shirt is loved for its soft texture, lightweight construction and natural breathability, which keeps its wearer feeling every bit as cool as they look.

Although you may be tempted to switch yours for a hardy denim version in autumn, don’t reach straight for the heavy guns just yet – chambray is a true all-rounder that can be worn twelve months a year with the right layering.

As we enter fall, pair your chambray button-down with classic indigo jeans (a darker shade is a must) for a subtle tonal mismatch that’ll smartly navigate risky double denim territory. Ground the outfit by shrugging on a heritage tweed overcoat and lace up in some smart tan brogue boots for a rugged, workerwear-inspired look.

Alternatively, use your chambray shirt to add a textural highlight to outfits. When worn with black slim-fit jeans, brown Chelsea boots and a white crew neck tee, your shirt will add an extra layer of interest to your off-duty getup.

Finally, a chambray style is the ideal substitute for your formal shirts on dress-down days in the office. Team with a knitted tie, slim-fitting blazer and smart wool trousers for a sophisticated cold-weather ensemble that’s full of depth and character.

Men's Chambray Shirts In Autumn/Winter Outfit Inspiration Lookbook

Kip 2015Beckham For Belstaff 2015Mango Man AW14Massimo Dutti Spring 2015Crombie AW15Ramsey SS12Dondup AW15Massimo Dutti March 2015Mango Man SS13Mango Man SS13Mango Man SS15J.Crew Pre-AW13

5. The Fine Gauge Jumper

A classic cotton or linen-blend crew neck jumper is a true summer essential, especially if your local climate is prone to unpredictable weather or nippy early mornings and late evenings.

Yet the qualities that make this piece so suited to the warmer months of the year will allow you to continue wearing it well into autumn/winter, where it makes arguably the perfect trans-seasonal layering piece.

Breathable and lightweight, slip your jumper on underneath a blazer or jacket for an extra layer of insulation against the elements, throw it on over the top of your wardrobe staples – shirts, tees, polos – to make it the focal point of your look (especially if it comes in a bold, summer-ready colourway), or wear it alone with a pair of chinos or jeans if the weather is particularly mild (100 per cent cotton styles won’t cause skin irritation like wool versions can).

It also makes a superb addition to your professional wardrobe. Slot it between your shirt and suit jacket to bring character and textural interest to your nine-to-five looks.

If going down this route, be cautious when it comes to colour. That bright yellow jumper that looked great teamed with your white chino shorts on holiday this year is probably not going to secure the same admiring glances in a stuffy corporate office. Instead, reach for knits in deeper, richer hues such as teal, burgundy and camel, which will inject life into your often monotonous formalwear, all while retaining a sense of professionalism.

Men's Leather Loafers In Autumn/Winter Outfit Inspiration Lookbook

River Island AW15Selected AW15Sanahunt SS13Matalan AW15Burton AW14H&M Spring 2015Zara AW15River Island AW15Mango Man Autumn 2015Acquascutum SS15Massimo Dutti 2015Suitsupply SS15

Final Word

When it comes to bridging the gap between seasons, it pays not to throw the baby out with the bath water. Before you start stocking up on new autumn/winter gear, don’t forget those summer pieces that can easily be worked into next season’s outfits.

Chosen wisely, your new additions will breathe life into the pieces you’ve relied on all summer long.

Do you have an item of clothing that you can wear all year round? Do you shop seasonally or think of your wardrobe as more of a year-round solution?

Let us know in the comments section.