What to Wear with Shorts in 2014. Explained by 23 Experts.

I love wearing shorts. Sometimes I cant seem to find the right clothes to pair with shorts.

I have my own sense of fashion as everyone should. Yet there are so many different options to choose from. It can become difficult to understand what goes well with what.

I decided to gather opinions from fashion experts to help nail down some short essentials.

The question:

"What are your 3 favorite accessories to wear with shorts?"

I asked people who work in high fashion to street fashion.

Even though there is a large gap between styles. There are a few basics that will help everyone rock shorts on all occasions.

If you stick to these recommendations you can't go wrong. You will always be dressed to impress.

Responses listed in order they were received.

Brock Mcgroff - TheModestMan

A colorful, casual watch with a canvas strap, like the Timex Weekender.

A pair of plastic tortoise shell sunglasses like the Warby Parker Becketts or Ray Ban New Wayfarers.

A tan or navy braided belt, like this one from Docker's.

Aaron Marino - IamAlphaM.

1. Cool sunglasses

2. Cool fabric belt

3. White V-Neck T

Christopher Hogan - OffTheCuffDC

Effortless Gent - EffortlessGent

Antonio Centeno - RealMenRealStyle

A panama hat, Maui Jim Kapalua sunglasses, and probably some Koss earplugs

Andy Gilchrist - AskAndyAboutClothes

I’m not a shorts person, but I wear them to play golf so my primary ensemble would be a collared golf shirt, a fabric belt and golf shoes.  I don’t like the little anklet socks, but everyone at my country club wears them so I conform.  I guess they do help with a no sock line tan!   But occasionally (my wife and I live in Palm Desert, CA where everyone wears shorts all the time!) I will wear shorts out!  Never to a restaurant.  Mostly to a private patio/pool party.  Then the accessories would be a Tommy Bahama shirt, braided belt and leather woven shoes.  Again I don’t go sockless so I’d wear low, crew length socks pushed down a bit.

Jeremy Reeves - KinoWear

1) I like wearing a nice high-quality leather sandal. It's obviously very casual but if you can find a really high quality sandal, it stands out and brings it up a notch.

2) Whenever I'm wearing shorts I typically mix it with a tucked in collard shirt. Sometimes I'll even put on a long-sleeved shirt and roll up the sleeves, to mix it up.

3) I also like to make sure I have sunglasses. Such an easy way to add more style (and protect your eyes!) I usually clip them onto my shirt at the top bottom, which draws attention and pulls down the shirt just a little bit to show a little chest (just be careful how much chest you show or it can get awkward).

4) Bonus: If I'm wearing a watch with sandals, I usually like wearing one with a leather strap so it matches the sandals. 

Michael Williams - AContinuousLean

Sabir Peele - MensStylePro

Well Built Style - WellBuiltStyle

Jimmy Tran - Jimaaaaa YouTube

Three things that I would wear with shorts are short sleeve button downs, vintage NBA jerseys and tie dye t-shirts.

Ape - ApeToGentleman

Car Shoe loafers

Ray-Ban Wayfarer

Linen shirt (sleeves rolled up)

Kelvin - NotoriouslyDapper

With shorts I love to wear short sleeve pastel colored oxford shirts, slip on sneakers or Birkenstock sandals and a classic pair of wayfarers to block the sun!

Sam - LifeStyleBYPS

1. Canvas Sneakers (Preferably in white)

2. Leather Wrap Bracelet And Canvas Band Watch (preferably in Army Green or Navy) (If I'm wearing both together I'll make sure I'll wear both on the same hand)

3. Matte Black Wayfarer

And of course, A Pint of Cold Beer

William Tan - HisStyleDiary

My 3 favorite accessories to wear with shorts...Wearing shorts run the risk of looking too casual and sloppy at times.  They can be paired with  T-shirts, or roll up casual shirts,  but it what really helps to sharpens the look is to always wear it with the following 3 trendy accessories...

1) Casual Shoes ...definitely Rivieras Shoes for me: they are the king of stylish and comfortable casual shoes! They make a casual outfit looks much sharper vs the sloppy flip flops that many people wear around in the summer.

2) A nice style tote bag or a backpack.Tote: Example a Jack & Mulligan Tote. Back Pack: Marc By Marc Jacobs Back Pack.

3) Bunch of cool stylist bracelets : You could get some cool affordable ones from ASOS.com.

Max - TheRuggedMale

It depends on what you are doing in your shorts.  Unless you are hiking you should be wearing flip flops, not sandals, tevas, or bucs.

I personally only wear shorts during the day, unless I'm on vacation somewhere very warm. Sunglasses are a must, even if you are wearing them on your head. I prefer white linen shirt with sleeves rolled up, watch with wide leather band.

Andrew Villagomez - VeeTravels

3 accessories I like to wear with shorts: lightweight canvas shoes such as ones from Tretorn and TOMS, v neck tees, and a backpack or tote bag style depending on what kind of shorts I'm wearing. Favorite summer bags include styles from Herschel Supply, Coach and Frank & Oak.

Arthur - HommeStyler

I think the key to wearing to wearing shorts (aside from the fit, cut and length of the shorts) is pairing it with the right top and shoes. I'd say for slim-fit shorts, the easiest way to dress it up it to complement it with a fitted collar shirt. To dress it down, you can put on a basic tee. There's no set rule for what shoes one should wear with shorts, but if the sun is up, then car shoes are sure bet. Also, if the weather is sunny, always remember to put on a hat! 

Alex - MensLifeStyleGuide

Classic Luxury Timepiece

Leather belt


Brandon Michael Lee- Style-Me-Manly

Personally, when I wear shorts I do very simple styles… it’s either a smart casual or completely casual.

I personally do not find the whole “smart” or “office” shorts to be appropriate for formal, semi-formal or “office” environments… but that’s a personal opinion.

My rule of thumb is if the shorts are more on the smart spectrum, you want to wear a belt, collared shirt (tucked in) and some nice loafers.

The casual end of the spectrum would be flip flops and tank tops… trashy but cool LOL

In terms of accessories… I’m truly loving ankle bracelets right now… now for men, I mean woven leather style, not shiny dangly things… think more surfer sheek than belly dancer lol

Paul Fredrick - PaulFredrick

Joseph Ferraro - AnAffordableWardrobe

My three favorite shorts accessories are boat shoes, ribbon belts, and a ratty old Red Sox cap.

Michael Adams - Michael 84

1. Spain Havaianas - If I am going on a beach-type holiday and relaxing round a pool, flip flops are the way to go. I love my Spain Havaianas, they're comfortable and give a more individual and fun look. If going for something a bit smarter or require more walking around such as a city break, then I'd pick something light such as my Converse.

2. Ray Ban Aviators - Stylish and timeless. I own a few pair of sunglasses but my aviators are what I wear most of the time. The perfect style for any occasion.

3. White T-Shirt - A classic, well fitted white T-Shirt will always look good, the simplistic nature of this will mean you can be more creative with your pair of shorts, and add colours or patterns to your look.


I want to thank everyone who contributed. Your knowledge is valuable so I appreciate you all. Please share this with friends if you find this article useful.

Stay comfortable. Stay Awesome.

Michael Lamb

I discovered sweat shorts about 10 years ago. I fell in love with them, and I am glad I did.