Summer Footwear


When things start to heat up outside, one’s wardrobe pares down as well. Tweed and flannel gives way to linen and cotton; sweaters go back in the drawer and polo shirts make their seasonal debut.

The same holds true for footwear. Down south where your feet hit the pavement, changes are afoot.

It’s a given of course, that in the great scheme of things men do not have the incredible variation in style, functionality, materials and colors that women do when it comes to shoes. While some bemoan this situation, I find it a blessing. Without the need for a separate shoe closet, men easily have enough choice in their footwear wardrobe to create distinctive, classic and signature warm weather looks for every day of the week.

As I see it, there are four broadly defined categories on which to focus when getting dressed each morning. Each one dictates your overall choice of clothing and corresponding footwear.

Business Wear = traditional suits, formal office wear, important meetings, conservative blazer and dress trousers.
Traditional laced business shoes / slips-ins

Business Casual = general office wear, professional but not necessarily formal, wider range of sport coats paired with dress and casual trousers, finer polo shirts and dress khakis or chinos.
Lighter colored dress shoes / loafers / suede bucks / rubber soled casual shoes

Social = going out, lawn parties, social but not necessarily casual events
Driving moccasins / casual loafers with contrast stitching / boat shoes / canvas tennis shoes

Weekend Wear = casual, relaxing, friends and errands or chores
Boat Shoes / Camp moccasins / Birkenstocks & sandals / canvas tennis shoes

To me footwear is a component of an overall wardrobe; shoes should both stand out as your outfit’s foundation and also work with that outfit to tell a unified story.

Business wear and business casual do not really change much during warm weather. If wearing a business suit, traditional black, brown and cordovan footwear are still your best choices. These cap toes, oxfords, balmorals and slip-ins will also work with brighter shirt and tie combinations you may want to try out.

Some men like to switch to light colored dress shoes in warm months. This can be a difficult trick to pull off because softer colored leathers – creams, pale tans and other earth tones – can look both affected and aesthetically unsettling. It takes a very specific kind of outfit to provide the same level of professionalism and balance that traditional darker colors offer.

Mixed media footwear, cap toes done in leather and linen for example, can be elegant but should be paired with equally stylish tailored clothing and not necessarily a business suit. The mix of summery élan and boardroom sobriety usually don’t work together.

Linen, cotton and seersucker suits are a different story. For these classics, white or tan suede bucks complete the prototypical summer suit. Jaunty and timeless, white bucks in particular are the perfect match for the warm weather dressy/casual appeal of summer suits. Dark brown or cordovan lace ups and slip-ins can dress the outfit up a notch but I think that black is just too formal.

I have also seen white bucks paired with a dark navy linen suit. The effect was wonderful – very Great Gatsby, but not all a costume. The suit was extremely well tailored and the shoes were of a very high quality. What made it work though was the pairing of a linen “business” suit with the equivalent of summer “business” shoes. While still a little adventurous in a traditional office, it’s very natty.

Dressing for a business casual environment brings in a different class of footwear. When pairing your shoes with lightweight chinos, linen or other summer fabrics, penny loafers and boat shoes are traditional options that reduce the formality while still not straying into weekend territory. While loafers are widely accepted as a less formal dress shoe, boat shoes and their outdoorsy brethren are seen by some as an office interloper.

My fellow columnist Simon Crompton devoted a recent article to his distrust of the boat shoe in particular. While I almost always agree with this sartorial viewpoint, here I must dig in my sockless heels and revert to New England roots. Boat shoes, best embodied by the original Sperry Topsiders, are a staple of most East Coast wardrobes. They are, in my humble opinion, a classic all purpose casual shoe.

Where canvas trainers would be inappropriate, the boat shoe, aka “docksider”, strolls in without a second glance. I would never say that they are correct for all business casual environments, especially those with an emphasis on Business, but for most offices with a relaxed dress code they are just fine.

Part of the issue boils down to one’s personal casual style. Clothing-wise are you by nature formal or relaxed? My father, for example, has never owned a pair of jeans in his life. His weekend attire often consists of a button down oxford shirt, neat chinos and deeply polished Brooks Brothers loafers – or in the summer, docksiders. That’s just who he is.

I however, may wear old khakis with frayed cuffs, a faded polo shirt, ribbon belt and well worn canvas tennis shoes (or docksiders; without socks of course). When clothed for business I naturally gravitate toward a formal European sense of style and prefer English made footwear. But when dressing more casually my American genes take over. And truth be told, that is more of who I am when push comes to shove.

For some men the space between formal and casual is much tighter – like Simon or my father. Footwear is a good indicator of this personality trait. There is no wrong or right, it’s just personal taste as far as I’m concerned. For some, warm weather means only slight variations in the shoe department. For others, it is a celebration of the additional, often casual, options that lighter, brighter and less formal attire brings.


Chris Hogan, an association executive based in Washington, D.C., blogs at A lifelong interest in style and clothing led to sales and management positions at several Ralph Lauren stores and an active wardrobe consulting practice


  1. Nicola Linza says:

    You are correct here. I too feel strongly, especially for us with American roots, that there is something ‘so right’ about the classic American aesthetic for casual wear. I have on, right now, dark blue Sperry Topsiders, no socks, with pale Polo chinos, and a blue check Polo short sleeve cotton shirt.

  2. Who makes those wingtips?

  3. They are Brooks Brothers shoes – made by Peal & Co. The BB site shoes a slightly different version at the moment.

  4. Dear Simon
    I am a boy of 16 living in England and my question is regarding footwear. I have been wearing plimsolls for a few months now and i am totally bored with them. I am off to 6th form soon and i do not know what type of shoe to go for. I belive it is too early for me to go to smarter footwear, but i find the trainers my friends wear totally disgusting. My first thought was a pair of deck shoes, but i am not partial to wide shoes. Then i thought of a pair of suede loafers, but would they start to border on the ‘too smart for my age’ side. Do you have any suggestions?

  5. Matt,
    Though my name is not Simon, I feel compelled to answer your query. Why compelled? Partly because I know what it is to tire of footwear. Plimsolls, though they are one of the more bearable forms of sport shoe worn by young people – far better in style and shape than the crass, lumpy trainers that are astonishingly popular – are a little ubiquitous now. However, I also feel compelled to answer because of the subtle problem you consider you have; what to buy which is not ‘too-smart-for-your-age.’ Personally, you are never too young to dress properly. People might expect you to be dishevelled, sloppy and prone to popular trends in sportswear but that does not mean you should knuckle under and do what others do. The fact that you are thinking about deck shoes and suede loafers at your age is a credit to your growing sense of style. Others might point, sniff and even snigger but it is usually out of insecurity and fear of sartorial precociousness.
    However, as my memories of being 16 are still relatively fresh, I can see your point. If you are concerned and desirous of wearing ‘youthful’ shoes and want something other than plimsolls, a pair of loafers is a good idea. Suede ones are fabulous, but as you indicated, some of your peers might consider this a little too ‘advanced’ for their liking.
    These shoes from TopMan are of a good design and pretty good value, are very versatile; and go well with the slim and skinny youth fashion jeans. They are of the ‘penny’ design and there has been a mini-renaissance of this ‘college prep’ style. They might be worn by aging accountants but they always look best on the young.
    A shoe more suitable for winter might be something like a Chelsea boot (with elasticated sides) and for something very summery, to break completely from the plimsoll, could be the espadrille; again, not expensive and good with youth denim trouser styles.

  6. Matt,

    Thanks very much for your question. First, I want to commend you as did Winston, for even thinking about this issue at such a relatively young age (at least to me).

    Boat shoes might still be a good option because they offer a nice transition between casual trainers and more formal lace ups. As a New England Yankee, I feel a certain genetic obligation to promote the preppy ethos. However, if that is just not your style, I am perfectly happy to say that Simon’s suggestion of a classic “penny” style loafer is spot on.

    Loafers can work with jeans, khakis or dressy trousers. I tend to prefer a deep brown or cordovan, but black is also a versatile choice. Personally, I think suede loafers are doable for someone of your age, just don’t try to dress them up too much – nice jeans and a polo would be very nice.

    The main thing is that if you are going to make an effort to develop your own sense of style, don’t compromise. I remember buying my first pair of suede bucks and wearing them to school for the first time. I was not sure how to pair them with the right pants, but I did know that I liked the shoes and that they fit my style. I was worried that people might make fun of me or maybe think I was trying to act older, but in the end…..nothing. No one really commented and the weird looks I did get were from kids I didn’t like anyway.

    My good friend gave me some grief, but now they look to me for advice; so it all worked out. Don’t worry too much about what anyone else is going to think of your clothing choices. Something tells me that whatever you choose, it will be quite sharp. Feel free to update us on your progress or to ask any other questions.