How to Look Good in Shorts (Guys)

How to Look Good in Shorts (Guys)

I recently published my comprehensive shorts shopping guide, in which I go through all the information you need for putting together a chic summer look.

Sincerely, I feel that if I didn’t show you just how to wear your brand-new pair of shorts, I’d be doing you a disservice.

Here are five of my beloved shorts presenting outfits that women love.

Outfit 1

We begin with one of my all-time favorite spring and summer outfits, which consists of some flat front shorts, a short sleeve button-up shirt, and a great pair of espadrilles.

This colorful outfit is not only super casual to put together, but it also has a relaxed yet stylish aesthetic that is perfect for warm-weather situations when you want to look hot yet feel cool.

Let’s first chat a little bit about that stylish short sleeve button-up shirt.

If you hadn’t noticed, during the past few years, this specific kind of shirt has made a significant comeback, and happily, it has completely evolved from the horrible Charlie Sheen bowling shirt look.

The short sleeve button up’s relaxed fit and versatility let you wear it alone or layered over a t-shirt or tank top, which is one of its best features.

The shirt being worn here is made of linen, which is ideal for summer shirts because it is much lighter than cotton and offers more comfort and breathability.

I particularly like how the contrast between the lighter-colored shirt and the white shorts, as well as how the white buttons enhance the brightness of the lower half.

However, keep in mind that you should only wear one print per outfit to avoid having pieces that clash. If you’re looking for something a little more playful, you could always choose a fashionable print like a floral pattern.

You may see another version of this outfit here:

The color pattern is reversed, with a lighter shade on top and a darker shade below, which is probably the first thing you’ll notice.

As you can see, this arrangement is really effective. However, if I could change one thing, I would swap those pleated shorts with flat fronts rather than pleated shorts because they just make you a boy scout look.

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Outfit 2

Our next look is incredibly casual and couldn’t be simpler to put together. It’s a casual crew neck t-shirt that looks great with shorts and a pair of casual low top sneakers.

Focusing on getting the fit just right is the secret to making an outfit like this actually work for you. Take note of how the tee gently hugs the torso and biceps without being overly constricting, ending just below the belt.

The shorts come to a perfect stop right above the knee, where they break up the body and maintain a balanced appearance.

Similar to the previous outfit, this one has a really good look of colors, with a dark top half, a lighter bottom half, and dark shoes.

This could also work the other way around with the white tee, black or navy shorts and white sneakers. However, there’s something about this specific black and beige combination that simply really appeals to me.

Please also note how well the accessories are used in this instance. Sunglasses, a watch, and a baseball cap.  It is casual, straightforward, and stylish. Nothing is overly superfluous or intrusive, and each piece helps to make the outfit look better in a unique way.

If I had to change one thing about this outfit, I would choose a different pair of shorts that weren’t cuffed or distressed. Your shorts should never need to be hemmed or cuffed and should be the right length.

Outfit 3

The following outfit, which also features shorts, is more sophisticated but still very simple to put together.

This one includes some great olive-colored shorts, a long-sleeved button-up shirt, and some stylish loafers down below.

Here, I do not mean a dress shirt when I say long sleeve shirt. An Oxford shirt made of cotton, a shirt made of a lighter material like linen, or a shirt with a cool textured seersucker fabric are better choices.

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Although short sleeve shirts like crew neck tees or polos are frequently associated with summer, any man’s warm-weather wardrobe should also have a long sleeve option.

Its incredible versatility is the cause. It can be easily dressed up or dressed down depending on what you pair it with, somewhat like a pair of dark wash jeans.

Additionally, a high-quality Oxford is a menswear need because it may be worn almost year-round.

If you don’t already possess an Oxford shirt, I really recommend going out and buying a few in some versatile neutral shades. Oxford shirts come in a range of various shades. For a tidy and refined look, white always works.

I simply love how well this light blue one matches the olive shorts being worn on the bottom part.

Our footwear consists of some loafers, which go well with the shorts’ darker color of olive.

You could always swap out the suede slip-ons for a good leather penny loafer or you could keep things casual with my old favorite, the white leather sneaker, if you wanted to dress up this look even more.

Outfit 4

The next outfit is another example of how versatile the aforementioned long sleeve casual shirt is.

Here, a stylish long sleeve button-up is worn with blue shorts and white low-top sneakers, and it is layered over a well-fitting crew neck t-shirt.

A casual long sleeve shirt gives an additional layer of warmth when worn over a t-shirt or tank top, and the rolled-down sleeves can also add some additional sun protection.

But don’t be scared to keep them rolled up and show off a bit of that gorgeous forearm that women love.

Additionally, if you do own a tank top, kindly be aware that this is the only way you should be wearing it in public. When worn over a long sleeve shirt or a short sleeve button-up shirt, tank tops just look relaxed and super stylish as opposed to how super lazy they appear when worn alone.

I particularly enjoy how the shirt’s stripes contrast with the plain-colored shorts and sneakers.

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Remember that each outfit can only have one printer pattern. It’s super straightforward, super stylish, and super summery.

Outfit 5

For our last outfit, we have a stylish pair of shorts worn with some classic Converse style low tops and a crew neck sweater, which has been layered beautifully over a t-shirt.

Crewneck sweaters are typically associated with fall or winter for guys, but let’s not forget that spring and summer may also feel a touch cool, especially at night.

Since it can be worn over crew neck t-shirts and long sleeve shirts, as is the case here, a decent sweater is a wise investment.

I love the hue of this one. It is definitely worthwhile to purchase a traditional heather gray, white, or even navy sweater because these shades go well with a variety of other pieces.

Additionally, they can be worn virtually all year long.

Initially, you might assume that mixing grays and whites wouldn’t really work, but as you can see here, these colors are so neutral that they can be combined super easily for a laid-back and relaxed look.

However, if you are particularly pale, I would recommend using deeper shades than those displayed above, since the milder color scheme might simply happen to make you look even paler.


how to look good in shorts men


  • Christopher

    Christopher has 9+ years of experience as a creative fashion designer who stays current with the latest trends.

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