Top 5 Men’s Transitional Footwear Styles

Style Purgatory

The transitional period between winter and spring is awkward, isn’t it? No longer cold enough to warrant breaking out the big guns – sturdy work and hiking boots – but not yet warm enough to bare your feet in that new pair of burnished leather sandals either. It’s a no man’s land, and you’re just not quite sure what to wear to tread in it. So what’s the solution? Much like your wardrobe, your footwear collection will benefit from a few key additions to take you through this difficult in-between phase in style. Not only will this add variety to your looks after months of wearing the same chunky shoes and boots, it will also increase your existing footwear’s longevity. Why? The longer you rely on just one or two pairs of shoes, the faster you wear down the heels and wrinkle the uppers. But before delving into the best transitional options available, it’s worth heeding these three pre-purchase pointers:

  1. Remember that quality will always better quantity, especially when you only need one or two pairs to help bolster your collection.
  2. You really do get what you pay for. Shoes that you purchase from footwear’s most formidable brands like Barker, Church’s or Grenson will always trump high street versions when it comes to durability and comfort.
  3. Take advantage of mid-season sales. With the lion’s share of stores offering discounts to clear stock midway through the season, there are plenty of bargains to be had.

Now that you’re primed, here are the principal styles that should be on your radar for the months ahead:

Desert Boots

The undisputed king of in-between. It’s not quite a formal boot, but it’s not quite a casual shoe either. A classic chukka silhouette that’s traditionally comprised of a suede upper and crepe rubber sole, there’s not a lot that these won’t go with. Desert boots sit in the smart-casual sweet spot, which means you can team them with a pair of your favourite jeans, a button-down shirt and thick shawl neck cardigan and look considerably smarter than you should – given the little effort it requires. Or, for a slightly more military feel, you can chuck them on with some beat up Dockers chinos, a well-cut crew neck T-shirt and bomber jacket on the weekend. Even if you already own a classic beige/tan suede design, they now come in such a myriad of colours, fabrics and price points that there’s no reason why you can’t add another pair to your collection.

Transitional Lookbook Inspiration

Men's Desert Boots - Transitional Outfit Inspiration Lookbook

Burton SS15Banana Republic AW14Digel SS12AllSaints SS13He By Mango SS13Digel SS15He By Mango AW13New Look SS15Faconnable AW13Office AW14Boohoo Man AW13Massimo Dutti SS15
Key Styles

Recommended Brands: Clarks Originals, ASOS, Kurt Geiger, Ted Baker, H By Hudson, River Island, Mark McNairy

  • Clarks Desert Boots In BlackClarks Desert Boots In Black
  • Asos Desert Boots In SuedeAsos Desert Boots In Suede
  • He By Mango Suede Desert BootsHe By Mango Suede Desert Boots
  • Asos Desert Boots In SuedeAsos Desert Boots In Suede
  • He By Mango Suede Desert BootsHe By Mango Suede Desert Boots
  • River Island Brown Clarks Originals Suede Desert BootsRiver Island Brown Clarks Originals Suede Desert Boots
  • Kg By Kurt Geiger Suede Desert Boots NavyKg By Kurt Geiger Suede Desert Boots Navy
  • H By Hudson Cruise Leather Desert BootsH By Hudson Cruise Leather Desert Boots
  • Kg Kurt Geiger Godfrey Leather Desert BootsKg Kurt Geiger Godfrey Leather Desert Boots
Chukka Boots

One of the toughest decisions we all face – no matter the season – is what the hell to wear on our feet for a night out. Unless you’re likely to wind up at a warehouse rave, trainers don’t cut it, but on the other hand, your best brogues/Oxfords are probably slightly too formal and precious for what you’ve got planned. Don’t sweat it, get your hands on some chukkas. Opt for a classic black or dark brown leather design and you’ll have a pair of versatile, easy to wear boots that will complement all of your going out looks. Try wearing them with a printed shirt and straight/slim-leg jeans, hems neatly rolled up, if you want to make a statement, or team with a pair of chinos, Oxford shirt and lightweight knit for something solidly smart-casual.

Transitional Lookbook Inspiration

Men's Chukka Boots - Transitional Outfit Inspiration Lookbook

Ramsey AW13H&M 2013Bellfield AW14River Island AW13He By Mango AW12Next AW14H&M Spring 2013He By Mango AW13Dunhill SS15John Lewis AW14AllSaints AW13River Island Aw13
Key Styles

Recommended Brands: Topman, Ted Baker, River Island, ASOS, Grenson, Red Wing, Dr. Martens

  • Topman Hudson Houghton 2 Brown Leather Chukka BootsTopman Hudson Houghton 2 Brown Leather Chukka Boots
  • Base London Turmeric Chukka BootsBase London Turmeric Chukka Boots
  • Asos Chukka Boots In LeatherAsos Chukka Boots In Leather
  • Ted Baker Torsdi Leather Chukka BootsTed Baker Torsdi Leather Chukka Boots
  • John Lewis Chumbley Leather Chukka BootJohn Lewis Chumbley Leather Chukka Boot
  • River Island Brown Leather Chukka BootsRiver Island Brown Leather Chukka Boots
  • Grenson Marcus Suede Chukka BootsGrenson Marcus Suede Chukka Boots
  • Tods Rubber-soled Suede Chukka BootsTods Rubber-soled Suede Chukka Boots
  • George Cleverley Nathan Suede Chukka BootsGeorge Cleverley Nathan Suede Chukka Boots
Suede Brogues

Sure, a pair of chunky-soled brown leather brogues is ideal for dashing to the office when it’s wet and windy out, but if all you’re likely to battle is a brisk springtime breeze, do you really want to be lugging around that extra weight? Swap leather for suede. Suede brogues still communicate the formality of a leather brogue, but are lighter, much more spring-appropriate and will add natural texture to any look. But with great texture, comes great responsibility. Be sure to care for suede styles by applying a waterproofing stain-repellent spray and regularly brushing off surface dirt with a soft-bristled suede brush.

Transitional Lookbook Inspiration

Men's Suede Brogues - Transitional Season Outfit Inspiration Lookbook

Mango Man SS15Woolrich SS15Dune AW14He By Mango SS14Office AW14Digel SS13He By Mango SS13Digel SS12He By Mango AW12Gant SS14Burton SS15Burton SS14
Key Styles

Recommended Brands: Grenson, Church’s, Cheaney, Ted Baker, Paul Smith, Dune, Aldo, Oliver Sweeney, Bertie

  • Asos Brogue Shoes In SuedeAsos Brogue Shoes In Suede
  • H By Hudson Francis Suede BroguesH By Hudson Francis Suede Brogues
  • Ted Baker Hontarr Suede BroguesTed Baker Hontarr Suede Brogues
  • Dune Rayman Wingtip Suede Brogues TanDune Rayman Wingtip Suede Brogues Tan
  • Ask The Missus Cardinal Brogue Lace Beige SuedeAsk The Missus Cardinal Brogue Lace Beige Suede
  • Frank Wright Fry Round-toe Brogue ShoesFrank Wright Fry Round-toe Brogue Shoes
  • Oliver Sweeney Ldn Bradley Wc DerbyLdn Bradley Wc Derby Oliver Sweeney
  • Paul Smith Aldrich Wc DerbyAldrich Wc Derby Paul Smith
  • H By Hudson Haddow Suede BrogueHaddow Suede Brogue H By Hudson
  • River Island Navy Suede Formal Lace Up BroguesRiver Island Navy Suede Formal Lace Up Brogues
  • Paul Smith Shoes & Accessories Grand Suede BroguesPaul Smith Shoes & Accessories Grand Suede Brogues
  • Grenson Stanley Suede Brogues 1013856Grenson Stanley Suede Brogues 1013856
Leather Trainers

Technically, trainers should really go into hibernation for winter (though given their popularity in recent seasons, you’d hardly think it). After all, do you really want to risk covering your brand new pair of kicks in a series of water and snow stains? Once the worst of the cold weather is over, though, leather trainers should be your casual go-to. A minimal, chunky soled white pair is an essential addition to any style-conscious gent’s SS15 wardrobe and can be combined with everything from sweatshirts and jeans to tailored separates – as plenty of recent fashion week attendees have shown. Although white trainers are trending, don’t sleep on black leather styles – they are still versatile enough to be dressed up or down (see lookbook below) and are arguably more practical.

Transitional Lookbook Inspiration

Men's Minimal Black/White Leather Trainers - Transitional Season Outfit Inspiration

Banana Republic AW14Banana Republic SS15Mango Man SS15J.Crew September 2014H&M SS15Cerruti 1881 SS15Club Monaco AW14New Look SS15Selected Homme SS14Windsor. SS15Club Monaco AW14Burton SS15
Key Styles

Recommended Brands: Vans, Nike, Common Projects, Filling Pieces, Mr Hare, adidas, Nike, New Balance, Converse

  • Vans Classic Slip-on Leather Shoes In BlackVans Classic Slip-on Leather Shoes In Black
  • Adidas Stan Smith Trainers In White And RedAdidas Stan Smith Trainers In White And Red
  • Vans Era PrmVans Era Prm
  • He By Mango Leather SneakersHe By Mango Leather Sneakers
  • Adidas Originals Superstar 80s Trainers In White And BlackAdidas Originals Superstar 80s Trainers In White And Black
  • New Balance 996 JpNew Balance 996 Jp
  • Mr. Hare Cunningham Low-top Leather Trainers 1014024Mr. Hare Cunningham Low-top Leather Trainers 1014024
  • Common Projects Original Achilles Leather SneakersCommon Projects Original Achilles Leather Sneakers
  • Converse Jack Purcell Leather SneakersConverse Jack Purcell Leather Sneakers
Boat Shoes

OK, granted it’s a bit of a curveball, but hear us out. While the quintessentially summery boat shoe probably won’t be much good to you right now, there’s no reason you can’t reach for them once temperatures rise slightly. Not only are they supremely comfortable on your feet, but if you pick up a leather pair in a neutral colour like black, navy, white or grey, then you won’t need to worry about them looking out of place. While a few seasons ago we’d have advised you to go sockless with boat styles, we’re now spoilt for choice with the range of ‘invisible’ socks for men on the market, which give you the desired bare ankle appearance without the sweat and hygiene issues. That said, a complementary coloured ribbed pair won’t negatively affect your style credibility either, so long as you bear in mind our tips for matching your socks to your outfit. Wear this silhouette with Riviera-inspired chinos and tailored shorts rather than denim, and round out the remainder of your look by taking inspiration from the shoe’s design – i.e. if you’ve opted for a nautical blue, red and white version, then continue the theme with a well-cut Breton T-shirt. On the other hand, if you’ve chosen a pair in timeless brown leather, try a simple white button-down.

Transitional Lookbook Inspiration

Men's Boat/Deck Shoes - Transitional Season Outfit Inspiration Lookbook

He By Mango SS13L.B.M. 1911 SS15Tommy Hilfiger SS14Digel SS12Ted Baker SS12Nordstrom SS14He By Mango SS13Mango Man SS15Tommy Hilfiger SS14Selected Homme SS14Woolrich SS14He By Mango SS14
Key Styles

Recommended Brands: Sebago, ASOS, Mango Man, Kurt Geiger, Sperry, Quoddy, Timberland, Lacoste, Ralph Lauren, J.Crew

  • He By Mango Leather Boat ShoesHe By Mango Leather Boat Shoes
  • Asos Boat Shoes In LeatherAsos Boat Shoes In Leather
  • He By Mango Leather Boat ShoesHe By Mango Leather Boat Shoes
  • Kg Kurt Geiger SorrentoSorrento Kg Kurt Geiger
  • Kg Kurt Geiger PhillipPhillip Kg Kurt Geiger
  • Sebago Docksides – Boat Shoes – ChocolateSebago Docksides - Boat Shoes - Chocolate
  • Sperry Top-sider Authentic Original Leather Boat ShoesSperry Top-sider Authentic Original Leather Boat Shoes
  • Quoddy Leather Boat ShoesQuoddy Leather Boat Shoes
  • Sperry Top-sider Authentic Suede Boat ShoesSperry Top-sider Authentic Suede Boat Shoes
Final Word

The start of the transitional season shouldn’t mean having to wear out your winter footwear, nor should you have to start donning summer-specific styles while it’s still a little too wet and windy out. Look to add one or two of these key footwear silhouettes to your collection and you’ll be ready for anything, no matter how changeable the weather. What are your trans-seasonal footwear staples? Let us know in the comments section below.

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