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10 Transitional Season Style Tips

10 Transitional Season Style Tips

It’s time to surrender your shorts and pack away those espadrilles, because we’re calling last orders on summer. But rather than lament the sunny season’s passing, we’re looking forward to autumn and all the opportunities to pile on the style that its inclement weather presents.

To help transition your wardrobe to the colder months seamlessly, here are ten top tips for dealing with this awkward in-between period, and the fashion dilemmas it brings with it.

1. Your Outer Layer Should Be Weatherproof

Much like the Great British Summer, the autumnal days ahead are sure to bring their fair share of torrential downpours, punctuated by the occasional dry spell, which means you need to equip yourself accordingly.

Technical rain coats – think robust outerwear from brands such as Stutterheim, Rains and Barbour – should be high on your list of wardrobe priorities for the season ahead.

Mercifully, weatherproof top layers have undergone a serious image upgrade in recent years and now come in sharp, contemporary silhouettes that look less trainspotter and more trendsetter. If we can’t convert you to a hardy mac or fisherman’s jacket, then keep an eye out for bombers in water resistant waxed/coated cottons.

Men's Lightweight Rain Jackets and Waterproof Macs - Transitional Season Outfit Inspiration Lookbook

scotch & soda Amsterdams Blauw aw15 RESERVED AW15 DRYKORN AW15 Zara AW15 Aquascutum SS15 Jigsaw AW15 Burberry Black Label SS15 Dondup AW15 Mackintosh SS15 Zara AW12 Next Spring 2015 J.Crew Casual 2015

Key Pieces

  • RAINS SHORT WATERPROOF JACKETRains Short Waterproof Jacket
  • RAINS LONG JACKETRains Long Jacket
  • J.CREW BARBOUR EQUESTRIAN BEDALE JACKETJ. Crew Barbour Equestrian Bedale Jacket
  • STUTTERHEIM STOCKHOLM RAINCOAT BLACKStutterheim Stockholm Raincoat Black
  • FJALLRAVEN GREENLAND JACKET AUTUMN LEAFFjallraven Greenland Jacket Autumn Leaf
  • STONE ISLAND MEMBRANA TC BOMBER JACKET NAVYStone Island Membrana Tc Bomber Jacket Navy
  • A.P.C. COTTON AND WOOL-BLEND GABARDINE RAINCOATA.p.c. Cotton And Wool-blend Gabardine Raincoat
  • PATAGONIA TORRENTSHELL WATERPROOF SHELL JACKETPatagonia Torrentshell Waterproof Shell Jacket
  • G9 MODULAR ARMHOLEG9 Modular Armhole

2. Invest In An Overshirt

Arguably one of the most important pieces of armour in your transitional season arsenal, a quality overshirt strikes the perfect balance between shirt and jacket. A shacket, if you will.

On warmer days, when a coat would be overkill, it can be thrown over a T-shirt for additional protection against the elements. When the mercury begins to drop, however, it can be slotted underneath your coat as an insulating mid-layer.

It’s like a sartorial Swiss Army knife with versatility and adaptability at its core. Our favourite styles come in earthy hues or buffalo checks and are constructed from wool, flannel or heavyweight cotton.

Men's Overshirts - Transitional Season Outfit Inspiration Lookbook

New Look AW15 J.Crew AW13 River Island AW15 Primark AW14 River Island AW15 Zara AW15 M.Grifoni AW13 AllSaints September 2014 F&F Clothing AW14

Key Pieces

  • ALLSAINTS EARTH WORK SHIRTAllsaints Earth Work Shirt
  • ASOS HARRIS TWEED OVERSHIRT WITH STRIPEAsos Harris Tweed Overshirt With Stripe
  • TOPMAN KHAKI LONG SLEEVE DOUBLE POCKET CASUAL OVERSHIRTTopman Khaki Long Sleeve Double Pocket Casual Overshirt
  • RIVER ISLAND ECRU HERRINGBONE UTILITY OVERSHIRTRiver Island Ecru Herringbone Utility Overshirt
  • RIVER ISLAND DARK RED SHIRT JACKETRiver Island Dark Red Shirt Jacket
  • PATAGONIA FJORD FLANNEL SHIRT FEATHER GREYPatagonia Fjord Flannel Shirt Feather Grey
  • OUTERKNOWN EVOLUTION REVERSIBLE SHELL SHIRT JACKETOuterknown Evolution Reversible Shell Shirt Jacket
  • OLIVER SPENCER LOUNGEWEAR COTTON-FLANNEL OVERSHIRTOliver Spencer Loungewear Cotton-flannel Overshirt
  • FOLK DENIM SHIRT JACKETFolk Denim Shirt Jacket

3. Boots Are Your Friends

We love summer. But there’s a lot to be said for winter and the slew of hardy footwear options it serves up.

Worker boots from brands such as Red Wing, Timberland and Hudson score high on our wish list and are strong options for guys keen to unleash their inner Brother Nature. But if you’re in need of footwear that keeps your loaves protected from the unpredictable autumnal elements and can be dressed up or down on your say so, it’s a pair of leather Chelsea boots you need.

Able to be teamed with a suit as easy as they can jeans and a leather jacket, Russell & Bromley, R.M. Williams and Cheaney offer a wide selection of styles that will effortlessly adapt to any occasion.

Men's Chelsea Boots - Transitional Season Outfit Inspiration Lookbook

Primark AW15 Reserved AW15 Zara AW15 Michael Kors AW15 Ay Not Dead AW15 Drykorn AW15 Selected Homme Jeans AW14 Burton AW14 Zara Edition AW13

Key Pieces

  • REISS CHESTER LEATHER ZIP BOOTS BLACKReiss Chester Leather Zip Boots Black
  • R.M. WILLIAMS LEATHER CHELSEA BOOTSR.m. Williams Leather Chelsea Boots
  • CHEANEY GODFREY LEATHER CHELSEA BOOTSCheaney Godfrey Leather Chelsea Boots
  • RUSSELL & BROMLEY BEECHWOOD CLASSIC CHELSEA BOOTRussell & Bromley Beechwood Classic Chelsea Boot
  • ALDO MARKINAldo Markin
  • RIVER ISLAND CHELSEA BOOTRiver Island Chelsea Boot
  • CLARKS ORIGINALS DESERT BOOT TAN TUMBLED LEATHERClarks Originals Desert Boot Tan Tumbled Leather
  • A.P.C. GERMAIN BOOT DARK BROWNA.p.c. Germain Boot Dark Brown
  • GRENSON ALFRED BROGUE BOOT BLACKGrenson Alfred Brogue Boot Black

4. Multiple Thin Layers > A Single Heavy Layer

You know you’re slap bang in the middle of a British autumn when it’s freezing one second and boiling the next.

The key to outfoxing the sudden rise and fall in temperature is to keep your outfit as adaptable as possible, comprising multiple, lightweight layers that can be thrown on and peeled off at a moment’s notice.

Importantly, each of these pieces needs to work on its own as the outermost layer and should be constructed from natural, breathable fabrics, such as cotton or wool.

Men's Lightweight Layering - Transitional Season Outfit Inspiration Lookbook

AllSaints August 2015 Olzen AW14 Acquascutum AW15 Reiss SS15 Burton AW15 Pull & Bear Daily Standards AW15 Topman AW15 Aldo AW15 Mango Man AW14

5. Carry A (Practical) Bag

Not only does an eye-catching backpack have the power to turbo charge your look, but it’s essential for shuttling about and stowing those extra layers when you’re darting between a hot office, cold street and stifling Underground.

And, naturally, you’ll need somewhere to store your compact umbrella and weather-defying hair products while you’re at it, so picking up a pocket-laden design from a specialist such as Fjallraven, Herschel or Sandqvist makes total sense, right?

  • REISS GIANI LEATHER BACKPACK BLACKReiss Giani Leather Backpack Black
  • RIVER ISLAND BLACK BLOCK PANEL BACKPACKRiver Island Black Block Panel Backpack
  • HE BY MANGO CONTRAST-APPLIQUE CANVAS BACKPACKHe By Mango Contrast-applique Canvas Backpack
  • RAINS MESSENGER BACKPACKRains Messenger Backpack
  • HERSCHEL SUPPLY CO 22L RETREAT BACKPACKHerschel Supply Co 22l Retreat Backpack
  • SANDQVIST VIDAR BACKPACKSandqvist Vidar Backpack
  • UNIQLO COMPACT UMBRELLAUniqlo Compact Umbrella
  • M&S COLLECTION SHOWERPROOF AUTOMATIC OPEN WOODEN CROOK HANDLE UMBRELLAM&s Collection Showerproof Automatic Open Wooden Crook Handle Umbrella
  • FULTON CROSS PRINTED UMBRELLAFulton Cross Printed Umbrella

6. Swap Bold Brights For Richer, Deeper Hues

There are no hard and fast rules to follow in terms of colours to wear during the cooler months. But if you want your wardrobe to look and feel seasonally-appropriate, then eschewing bright and bold hues in favour of richer, earthier tones – which will warm up your complexion and draw some nice parallels with the falling leaves (poetic much?) – comes highly recommended.

Combine a palette of burnt orange, burgundy, mustard and bottle green with your staple indigo denim and brown leather Chelsea/brogue boots to form the building blocks of an on-point transitional wardrobe.

Men's Autumnal Colours - Transitional Season Outfit Inspiration Lookbook

El Burgues AW15 J.Crew October 2014 Samsoe Samsoe AW15 Burton AW14 IKKS AW13 Tommy Hilfiger AW15 New Look AW15 Paul Shark AW15 Michael Kors AW15 Gant Rugger AW15 Massimo Dutti 2015 J.Crew AW15

Key Pieces

  • ALLSAINTS NATALKA CREW TSHIRTAllsaints Natalka Crew Tshirt
  • FARAH OXFORD SHIRT SLIM FITFarah Oxford Shirt Slim Fit
  • JACK & JONES SLIM FIT STRETCH CHINOSJack & Jones Slim Fit Stretch Chinos
  • REISS SABER TEXTURED KNIT JUMPER BORDEAUXReiss Saber Textured Knit Jumper Bordeaux
  • RIVER ISLAND ORANGE HERRINGBONE UTILITY OVERSHIRTRiver Island Orange Herringbone Utility Overshirt
  • HE BY MANGO 5-POCKET COTTON TROUSERSHe By Mango 5-pocket Cotton Trousers
  • COS SLIM-FIT STRETCH-COTTON TWILL BLAZERCos Slim-fit Stretch-cotton Twill Blazer
  • REISS WISH KNITTED POLO SHIRT BORDEAUXReiss Wish Knitted Polo Shirt Bordeaux
  • ACNE STUDIOS JENA WOOL SWEATERAcne Studios Jena Wool Sweater

7. Opt For Thicker Versions Of Your Summer Favourites

Sure, the weather’s on the turn, but that doesn’t mean you have to abandon your signature style altogether.

Instead of flipping your sartorial vibe on its head, simply opt for heavyweight options of your current warm-weather staples. For example, lightweight stretch denim gives way to hardy raw or selvedge jeans, while cotton chinos should be substituted for twill versions.

Likewise, you can shake up your shirt collection by upgrading from no-frills cotton button-downs to thicker flannel or denim styles.

Essentially, you’re keeping your go-to outfit combinations the same, but reinforcing your defences against the elements. Think of it as exchanging your current duvet for one with a heftier tog value.

  • J.CREW SUN-FADED SLIM-FIT COTTON-TWILL CHINOSJ.crew Sun-faded Slim-fit Cotton-twill Chinos
  • RRL SLIM-FIT SELVEDGE DENIM JEANSRrl Slim-fit Selvedge Denim Jeans
  • EDWIN ED-80 SLIM TAPER JEAN UNWASHED RAINBOW SELVEDGEEdwin Ed-80 Slim Taper Jean Unwashed Rainbow Selvedge
  • A.P.C. BUTTON-DOWN COLLAR DENIM SHIRTA.p.c. Button-down Collar Denim Shirt
  • BARBOUR CASTLEFORD SHIRT NAVYBarbour Castleford Shirt Navy
  • A.P.C. BUTTON-DOWN COLLAR CHECKED WOOL-BLEND FLANNEL SHIRTA.p.c. Button-down Collar Checked Wool-blend Flannel Shirt

8. Keep On Top Of Your Cold-Weather Complexion

Granted, you’ve just returned from a summer spent sunning yourself silly on some Mediterranean rock, where your skin had to withstand untold levels of tanning. But it’s time to consider how your skincare regime needs to be adapted to deal with the onset of autumn.

Bracing winds and cold temperatures can play havoc with your skin, drying it out and causing all kinds of chaffed nastiness. Therefore, it’s imperative you use a daily moisturiser, to keep you looking and feeling fresh-faced.

Keep your eye out for those infused with skin-repairing vitamin E, and don’t think that just because it’s winter that you don’t need SPF protection either. Although there may be clouds in the sky and puddles on the pavement, your skin is still prone to the sun’s UVA rays, which can lead to premature ageing.

Those of you who want to really stay on top of your cold-weather complexion can introduce a replenishing night cream to your evening routine, too. Moisturising last thing before bed is always a good idea because your skin tends to absorb creams better at night when it switches to repair mode.

Men's Recommended Day and Night Moisturisers

JACK BLACK DOUBLE DUTY FACE MOISTURISER SPF20 - Click To Buy Baxter of California Night Cream AHA - Click To Buy

9. Invest In A Footwear Protector Spray

With unpredictable downpours a token part of the transitional season, it’s important to take preventative measures when it comes to your footwear. So, to keep your shoes looking their best and prevent water seepage, regularly treat them with a quality protection spray.

That said, if – or rather when – your shoes do get caught in a heavy shower, then Scotchgard (or similar) may not be enough to save them. What’s important is that you let them dry naturally – heat can cause cracking and damage to the leather – and stuff them with newspaper to help maintain their shape and draw moisture from the upper. For more information on how to care for your footwear collection properly, be sure to check out our comprehensive shoe care manual.

Finally, it might be time to retire your suede and canvas styles for a few months. If you just can’t bring yourself to part with your suede desert boots, then at least check the weather forecast before you leave the house.

Recommended Shoe Protector Sprays

Scotchgard Water Repellent Shoe Protector - Click To Buy Kiwi Extreme Protector - Click To Buy

10. Switch Short Sleeves For Long Sleeves

Alright, it might sound like a bit of a no-brainer, but exchanging your summery tees and polo shirts for long-sleeved versions is a simple way of navigating autumn’s changeable weather while looking like a sartorially-accomplished pro.

Long-sleeved T-shirts in particular are having a moment right now, especially oversized, boxy-fit styles with a cool, skater edge to them. But there are smarter versions available, too, which can be sharpened up with trousers and a pair of Derbies for dress-down days in the office.

Topman, for instance, is offering a great selection of funnel neck long-sleeved T-shirts, which sit somewhere in between a roll neck and classic crew neck, and look particularly great in autumnal shades of mustard and maroon.

Men's Long-Sleeved Tops and Polo Shirts - Transitional Season Outfit Inspiration Lookbook

Massimo Dutti AW15 H&M AW15 Banana Republic Pre-AW14 Banana Republic Pre-AW14 Gap 2015 Zara AW15 Mango Man 2015 Mango Man AW15 AllSaints SS13

Key Pieces

  • HE BY MANGO HENLEY T-SHIRTHe By Mango Henley T-shirt
  • LEVIS HENLEY LONG SLEEVE T-SHIRTLevis Henley Long Sleeve T-shirt
  • FARAH RADWAY NAVY STRIPED TOPFarah Radway Navy Striped Top
  • ALLSAINTS PITT LONG SLEEVE CREWAllsaints Pitt Long Sleeve Crew
  • TOPMAN BROWN LONGLINE LONG SLEEVE T-SHIRTTopman Brown Longline Long Sleeve T-shirt
  • TOPMAN NAVY ROLL NECK LONG SLEEVE JERSEY T-SHIRTTopman Navy Roll Neck Long Sleeve Jersey T-shirt
  • FRED PERRY LONG SLEEVE TWIN TIPPED POLO MAHOGANYFred Perry Long Sleeve Twin Tipped Polo Mahogany
  • SUNSPEL LONG-SLEEVED COTTON-JERSEY POLO SHIRTSunspel Long-sleeved Cotton-jersey Polo Shirt
  • REISS MANSION MERINO WOOL POLO SHIRT CHARCOALReiss Mansion Merino Wool Polo Shirt Charcoal

Final Word

We all know the transition from summer to autumn is fraught with sartorial pitfalls, but armed with these ten tips you’re sure to cope with whatever Mother Nature throws at you in style this year.

How do you deal with this awkward in-between period? Any other advice or key pieces that we missed?

Let us know in the comments section.


  • Alan Posted On 3rd September 2015:

    LiquiProof is the only product you need to protect your footwear in the winter. It’s head and shoulders above those that are listed as you don’t need to keep applying it.

    I’ve found it very effective on suede and leather alike


  • Radio On The Tv Posted On 3rd September 2015:

    I’ve read a few things about these over shirts, any idea where to check some examples out on the highstreet?


    • Willis Posted On 4th September 2015:

      Hover your cursor over the pics. Personally like the Cos ones. Can be dressed up or down.

  • Anthony Posted On 4th September 2015:

    I would love to hear what you would recommend for the autumn/winter jackets which would be suitable for the pubs and clubs, to take on and off as needed.

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