Here is a picture of a man I saw in Los Angeles last month. The photo is enlarged so you can see the details of his clothing.
While I think this man is making a conscious effort to look good while wearing shorts; I see many ways we can help improve his look.
The Shirt: He looks like he is wearing a blouse. While I like the look of a casual dress shirt tucked in with shorts (and a belt), the shirt should fit the man. Notice the shoulder seams are hanging down over the edge of his shoulders? Ideally, they should be flush with the edge of his shoulder. The baggy waist needs no explanation. I trimmer fit would help this man look trimmer!
2. The Belt: Yes, belts do apply for shorts. If you are tucking your shirt in, please wear a belt. Leather belts are classy and elegant, but canvas belts, tie belts, etc. can be a fun alternative. NOTE: please keep the dying snake tucked into a belt loop. If you have a limp belt hanging off your hip, you need a shorter belt!
3. The Shorts: Flat front is the most flattering style and finding the balance between comfortable and fitted is key. Ideally, you should be able to keep your shorts up comfortably without a belt. However, your shorts shouldn't be so tight you can't sit comfortably in them. Ideally, you should be able to stick two fingers into your waistband and not feel like someone is stabbing you. If you can fit more than two fingers, your shorts might be too big (and baggy). This is the same rule of thumb for pants. Find shorts that fit as well as your best pants and you may have a winner.
4. Length: Like pants, length is key. For a timelessly good look, buy shorts that come down to the area right above your knee. I don't recommend shorts that come much below the knee (skater or capris style). If you are a shorter man, find shorts that come in a shorter inseam so you can show your knees a tad bit more and help elongate the look of your legs. Bonobos have some great options because they offer their shorts in regular length and long length. Taller men should do the opposite and find longer inseams so they don't show too much leg in order to balance their overall appearance; avoiding the dreaded "giraffe legs."
5. What shirt do you wear with shorts? A polo or T-shirt is a common choice. Both are quite casual, but at least the polo has a tad bit of decorum and can can get you a pass into the country club. Another recommended option is a casual, long sleeve dress shirt, worn comfortably fitted through the torso and unbuttoned at the neck. Roll the sleeves up, tuck the shirt in and finish it with a belt, loafers or boat shoes (no socks!) and you have a timelessly, elegant summer look.
Notice, I did not mention a baggy, silky bermuda shirt. I am not sure why men think these shirts look good on. They are the shape of a box, hang on the man's body like wilting foliage; and for larger men, all I need to say is they look even larger. So long Santa, no Christmas in July for us!
Polos are not the only thing you can wear with shorts. However, they
are a common choice for men who want a sporty look that is dressier
than a T-shirt. You can go the simple, solid route like the Lacoste
option on the right, or you can wear a polo with a bit more interest and
style such as the striped Penguin polo on the left. If you are a polo
guy, with a closet full of solid polos in every color of the rainbow, it
might be fun to try something new this summer like a patterned polo.
There are tons of options available.
6. Shoes with shorts: The key here is no socks (unless you are a fashionisto and making a statement with your dress socks & spectators). Casual loafers, boat shoes, drivers, clean and nice flip flops, slides and sandals are all options. For your best look, remember that athletic gear (including water sandals like TEVA's) are best paired with athletic clothing. Pair your REI shoes with REI clothing. If you are a grown, successful man who is still wearing his TEVA's everywhere he goes, it might be time to invest in some nicer leather, summer shoes.
When wearing shorts, your shoes help balance your look. If you have skinny legs, pick unobtrusive shoes like leather flip flops, drivers or top siders in a lighter color (brown is better than black if you are going on the dark side). For men with larger legs, pick shoes that have a more substantial look to them (more shoe showing; like a slide or boat shoe) to balance the size of your legs. More shoe for more leg; less shoe for less leg. It's not about length, it's about leg width.
7. The cut: Picking the right cut or style of shorts for you body is key. See the two examples below:
The shorts on the left are a straight cut. This style is the most flattering for most body types. The shorts on the left are a tapered cut. I do not recommend this style for men with larger waists or larger rear ends. The tapered style can easily give you the appearance of hips if you aren't careful. Some men can look great in this style, but I don't recommend it for most men.
In all honesty, men's shorts are probably one of my least favorite articles of men's clothing. However, as a realist, I understand they do have an important place in a man's wardrobe. Looking bad in shorts is quite easy. Looking good in shorts, takes a bit of effort and attention to detail, but it's well worth the effort. Stay cool this summer, and look your best while you are at it.
-Lisa Bruckner Trunk Club Expert

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