So here we are, the second part of my guide on shoes. In part one I talked about how to pick shoes to suit your personal taste, the difference between high street, designer and shoe specialists, and finally we talked about how to take care of your footwear. So what’s part two all about? Well much in the same vein as my previous article on timeless style, this article will contain information about all the classic shoes styles. These are the shoes that will never go out of fashion and will always serve you well. I’ll also throw in a quick word about recent trends, so without further ado, let’s get cracking.

Note: In this article and in the previous one there has been no mention of trainers, this is because Will’s article was pretty definitive and I urge you all to go check it out.

The Chelsea boot

The Chelsea boot for me really is the ultimate classic boot. I mean sure you can get other shoe styles in boot form, but the Chelsea boot originated as a boot and has maintained its popularity throughout time. Compare this to the newer modified boot styles such as brogue boots (cashing in on the popularity of the shoe) and you will see the Chelsea boot is draped in history, has been popular for a long time, and it will continue to be a timeless style going forward.

Originating in the Victorian era, they were essentially a horse riding boot, with the elastic on the ankle there to make it easier to get on and off (what this has to do with horses I have no clue). However, nowadays the Chelsea boot is a style institution and for good reason too; simple and elegant, yet robust and masculine, they are the definition of a menswear essential.

They are also very versatile; they work just as well with skinny jeans as they do with a suit. A perfect look would be combining them with a pair of dark blue jeans in a slim/skinny cut, with a white v or scoop neck t-shirt, finished off with a faded leather jacket – a casual and easy to wear outfit which is brought up a notch just by the presence of the more refined Chelsea boot.

Other key items to utilise with Chelsea boots would include: polo shirts, skinny jeans, slim/skinny suits, blazers and graphic tees. You can hit a Mod or Indie look with ease.

Men's Chelsea Boots Look Book and Outfit Ideas

  • Black Chelsea Boot
  • H By Hudson Scotsdale Chelsea Boots
  • JEFFERY WEST Dashwood chelsea boots
  • Paul Smith Side Zip Chelsea Boots
  • Ralph Lauren Purple Label Black Leather Chelsea Boots
  • Barker Eskdale Leather Chelsea Boots, Brown
  • Mens Red Wing Chelsea Boots

Loafers are another classic choice. The ultimate casual shoe; smarter than trainers, yet they seem to ooze a relaxed attitude – just slip them on and kick back. Think of them like elegant slippers that you can wear during the day. Every real gentleman should own a pair. More recent styles see the rise in popularity of detailing such as tassels and bows, whilst suede has become a very popular fabric option, with them coming in nearly every colour imaginable.

Loafers are perfect for summer, so I’d recommend twinning them with a pair of chinos (in your favourite style) and a crisp white shirt, maybe with some understated masculine jewellery on. Oh and don’t wear socks!

Items that look particularly great with loafers: chinos, tailored shorts, blazers and casual shirts.

Men's Loafers Look Book and Outfit Ideas

  • Rolando Sturlini Deconstructed Suede Loafers
  • Garbstore Billyslip Stone Penny Loafers
  • Paul Smith Shoes Brown Soft Leather Dwight Tassel Loafers
  • John Lobb Lopez Brown Suede Loafers
  • Gucci Suede Loafers
  • Grenson Clifford Leather Tassel Loafer
  • PATRICK COX Figure penny loafers black

The Derby shoe (confusingly called the Oxford by the Americans) is one of the two classic British gentleman shoes. The style of shoe is characterised by shoelace eyelet tabs that are sewn on top of the vamp, a construction method that is also sometimes referred to as “open lacing”, where the tongue is cut in one piece with the forepart.

That was all a bit complicated, so let me break it down: The derby shoe is an essential. If you’re stylistically minded you have two choices, black or brown. Pair it with a complimentary coloured suit for an everyday work look, but make sure you keep them in great condition (using the tips from part one) and well polished.

You can get away with using them with jeans or chinos, but make sure you keep the shoe colour less formal – tan is a great option for a more relaxed weekend look. Also remember to keep the top half of the outfit smart – a shirt, tie/bow tie with a jumper or a blazer? Don’t mess too much with a true classic.

Men's Derby Shoe Look Book and Outfit Ideas

  • ASOS Clean Point Derby
  • Hudson Black Lace Up Shoes
  • ASOS Pointed Derby Shoes
  • Paul Smith Shoes Pitney Black Darby Lace Up Shoe
  • Hugo Boss Black Chocolate Printed Texture Leather Shoes
  • Hoxton Lace-Up Shoe
  • Loake Magnum Leather Lace Up Shoes, Black
  • Loake Tetbury, Men's Lace Up Shoes
The Oxford

The Oxford shoe, the other classic option and one that in my research seems to be more popular among the fashion community. The Oxford shoe differs from the Derby in that the eyelet tabs that are stitched underneath the vamp; a construction method that is also sometimes referred to as “closed lacing”.

My advice for the Oxford remains the same as the Derby, invest in a pair of black or brown Oxfords and wear with a suit for work, weddings or formal occasions, or with a nice pair of dark slim jeans, a polo or shirt and a blazer (see above for derby advice).

Men's Oxford Shoes Look Book and Outfit Ideas

  • ALEXANDER MCQUEEN Gable ox lace–up shoes
  • John Lobb City II Leather Oxford Shoes
  • Trickers Regent Toe-Cap Oxford Shoes
  • Trickers Regent Toe-Cap Oxford Shoes

The brogue for me has become a timeless classic, although it has certainly reinvented itself as a true fashion piece within the last couple of years. The detailed stitching on the brogues gives it an understated edge, whilst the brogue is traditionally characterised by multiple-piece, sturdy leather uppers with decorative perforations (or “brogueing”) and serration along the pieces’ visible edges.

The brogue has become so popular recently due to its versatility, and this should be the key with any timeless item. It is versatile because it can work within just about any outfit; a beautiful pair of brown brogues are smart enough to be worn with a navy suit to the office, but also more of a playful style that can be paired with your jeans/chinos at the weekend. We have even been seeing people pair their brogues with tailored shorts and blazers over past seasons for their own take on the short suit.

The trends for brogues this year seem to be bold colours (more suited to casual everyday looks) which you can use as a focal point and contrasting colour to the rest of your outfit. Perhaps our favourite trend within the whole footwear market however is the rise of suede brogues which could be the perfect weekend shoe – a tan, brown or beige suede brogue will look amazing with any wash of jean you have in your wardrobe and will bring your outfit up a notch instantly.

Items that look particularly great with brogues: Anything and everything! Suits, jeans, chinos, tailored shorts, shirts polos, basics tees, denim jackets, the list is endless. Find your perfect pair that coordinates with the rest of your wardrobe – they will serve you very well if you look after them.

Men's Brogues Look Book and Outfit Ideas

  • River Island Washed Leather Brogues
  • Paul Smith Shoes Chocolate Miller Washed Brogue
  • Grenson Light Grey Leather Stanley Brogues
  • Yves Saint Laurent Lace-Up Brogues
  • GRENSON Dylan brogue
  • GRENSON William Dark Brown Grain Shoes
A Quick Note On Summer Shoes

When I say summer shoes, I mean the lighter styles – shoes that are perfect to wear with shorts. A true stylish gent only has three options this year for summer footwear: Boat shoes, desert boots and espadrilles. All three look great with shorts.

My advice would be to wear the desert boots and the boat shoes when you’re shopping or relaxing over a barbeque and save the espadrilles for the beach. And seeing as a picture says a thousand words, I have included a selection of photos which should inspire your outfits, as well as some of the latest styles to tempt you:

Men's Summer Shoes Look Book and Outfit Ideas

  • Toms Canvas Classic Espadrilles
  • Lacoste Rene Espadrilles
  • Pretty Green x Clarks Originals Desert Boot
  • COMMON PEOPLE Nash Choc Suede Desert Boots
  • Ben Sherman Cleg Desert Boots
  • PAUL SMITH - SHOES Hashbury Navy Dip Dye Shoes
  • hudson sunseeker boat shoe
  • Sperry Top-Sider Tan Leather Deck Shoe

So there we have it guys, part two of my guide on timeless shoe styles, I hope I inspired you to add some of these great classics in to your wardrobe. I look forward to hearing from you all in the comments section.


“What do nudists wear on casual Fridays?” – Author Unknown