Dressing Up Shorts

Heat is one of my worst enemies, and wearing shorts is one of the best ways for me to keep cool. However, looking smart with shorts is a bit trickier than with trousers. Things can turn too casual and, given their association with sports, too athletic too quickly.


Here are some ways I dress up my shorts.



First, the shorts themselves must look smart. The easiest way to think about smart shorts is that they should be like your chinos, only short. So you can safely use the same colors and fabrics as your chinos.


Beige, white, navy, and green are all good options, so long as there is sufficient contrast with the shirt. To avoid looking too “touch me and my dad will sue you,” I would stay away from pinks, salmons, and oranges. Aside from cotton, as shorts are more summery than chinos, linen is also a good option.


The shorts should end on or above the knee. How far up the knee, is a fairly subjective matter. I find that just above the knee cap is probably the perfect length for me. The white pleated shorts below are probably a bit short for some; in the picture below I'm wearing them as intended by the British Royal Navy – high with the shirt tucked in. The beige and green shorts below are probably a more ideal length and will fit most people.


The shorts should also be sufficiently trim (not tight) to elongate the legs. Shorts already interrupt the continuous line of the legs and wearing wider shorts will amplify the interruption. The exception to this is of course gurkha shorts (the traditional kind, not regular shorts with a gurkha-style waist). Gurkha shorts fall outside the scope of this article and perhaps warrant their own article.


British Royal Navy shorts (3CW Dress - General Duty Rig White). The shorts have a high rise and are made with side adjusters, extended tab, and pleats – designed to be worn with shirts tucked in.

Having said all of the above, however, the smartness of shorts is really lifted by the shirt and footwear, rather than the shorts themselves.


Second: the shirt. My go-to option is a long-sleeved button-down shirt (as pictured above and immediately below). Rolled-up long sleeves will wear similarly cool as short sleeves, but will look way smarter. I usually fold my sleeves twice as they will leave enough room to let air flow through. Another fold will restrict airflow and simply doesn’t look as smart.


While iGent gurus will tell you that you should never wear a dress shirt untucked, I think untucked shirts can look good with shorts, so long as the torso isn’t too long. Of course, if you want to look smarter, you can also tuck the shirt in. But this can be trickier as the shorts need to have sufficient rise. Moreover, it won’t wear as cool as wearing the shirt untucked.


The same shorts with shirts worn untucked and tucked. The shorts have a medium rise and as such can accomodate tucked-in shirts easily.

Going down the formality ladder, I'd usually go for long-sleeved polo shirts. Again, I usually wear mine rolled up (or simply pulled up, if the sleeves are elasticated). Going further down, a short-sleeved polo can also work. And if you must insist on wearing a t-shirt, I’d advise going for a Henley and avoiding any graphic shirts.


Third: the footwear. The smartest option is to wear loafers. Oxfords, derbies, and monks are not suitable in my opinion because of the high vamp. The formality of loafers is generally dictated by the height of the vamp. As such, mid and low-vamped loafers are most ideal. The shape of the last will also have an effect. Sharp, elongated, and chiseled lasts tend to look a bit too smart against the casualness of the shorts.


I generally despise “rules” relating to socks and loafers, but when it comes to shorts, I think no (or no-show) socks look best. Mid-calf socks with loafers look awkward and over-the-calf socks look too military.


My go-to choice is a burgundy or dark brown penny loafer worn with no-show socks. Tassel, bit, and plain loafers can also work, as well as more casual options, such as espadrilles and boat shoes. In terms of color, anything lighter than burgundy goes. If I could pick another pair of loafers, it’d probably be a snuff suede penny loafer. But they’re not as versatile, so I haven’t purchased one.


My go-to footwear by Grenson for dressing up shorts. Not the best quality, but one of the comfiest leather shoes I own due to the right fit and soft Ridgeway sole.

For a more casual look, sneakers can also look good. I’d go for plain, low-top, white sneakers. While mine are leather, canvas can also work. The key is to ensure that they are not mistaken for athletic shoes.


I’m more flexible in terms of socks when wearing white sneakers. Aside from no-show socks, light-colored, mid-calf socks can work for for a vintage tennis vibe, as below.


Vintage tennis vibes with the polo and white shoes and socks.

Written by: Nikki Krisadtyo