#OOTD: The Best Way to Wear Shorts this Summer

Editor’s note: You’ve surely seen this hashtag lots of different places, including on Instagram. But how does that carry over to real life? The #OOTD will take one great item and put together a versatile, stylish outfit around it. Look for past features here.

We’ve covered lots of ground here in past #OOTD posts on The Style Guide, but it seems we’ve skipped over a crucial style tip — the best way to wear shorts when it’s hot out. If you’re anything like me, it can sometimes be tricky to put away your denim, be it a slim pair of light wash jeans or something darker in color. They’re an easy style to wear across any season, to be sure — but from time to time, the weather really just calls for shorts. However, we’re not talking baggy cargo shorts. The best shorts for summer are more tailored in cut, lighter in terms of weight and fabric, and able to be worn with everything from a slim pocket T-shirt to a crisp polo and most styles in between. The same goes for the footwear you can match ’em with (and the pick you see below is a bit of a style swerve). The versatility of a slim pair of shorts is great news for all of us, particularly if you like your #menswear a bit more eye-catching.  And if you’re hesitant to ditch your denim or chinos because shorts feel too casual, know that you can take some risks when wearing tailored shorts (click that there link for tips). The below outfit starts things off slow, though. It’s one of the best ways to wear shorts this summer — at least in the opinion of your humble author.

Step 1: Buy shorts for summer. Step 2: Rock shorts for summer using this #OOTD.

Step 1: Buy shorts for summer. Step 2: Rock shorts for summer using this #OOTD.

The Shorts: JackThreads Chino Shorts, $39 — If you haven’t yet snagged a pair of chino shorts, these should be your go-to. Trying them on is free through the brand’s TryOuts program, and the fit and fabric should be reliable and stylish.

The Shirt: JACHS NY Cream-and-Blue Horizontal Striped Short-Sleeve Shirt, $89 — Upgrade from a casual T-shirt with an easygoing short-sleeve number that fits slim and broadens your chest thanks to the stylish stripes.

The Shoes: Jack Erwin Parker Driving Loafer in Navy Suede, $115 — We all love our stylish sneakers, but give some suede driving loafers a try. This particular pair is cut long and lean, and the navy color is especially sleek.

The Socks: Ministry of Supply Atlas No-show Socks, $11.98 — As crucial as it is to get your footwear choice right, it’s even more essential to grab some no-show socks to complement those kicks (especially driving loafers). Note that although the Grey color is shown in that photo, Black is what’s in stock now.
 The Belt: Arcade Belt Co. The Hudson Belt, $31.98 — So, you’ve got the shorts all set; don’t forget about a belt, particularly an upscale accessory that incorporates a neutral color and summer-appropriate texture.
The Watch: Invicta 8926 Pro Diver, $84.14 — Tough, reliable and stylish is the way to go; this is a casual watch that still looks crisp and plays off the rest of the outfit perfectly.
The Sunglasses: Randolph Engineering Aviator Sunglasses in Gunmetal, $209.98 — To top off an outfit that’s got a bit of flourish (particularly those driving loafers), grab some classic men’s sunglasses.
The Necessary Accessory: Manda Organic Sun Paste, $28.98 — When it comes to getting out this summer, taking care of your skin is a must. Doing so in an organic fashion is even better.
The Everyday Carry: Appointed Mini-Jotter, $9.98 — Not everyone is partial to writing things down, what with technology everywhere, but when out on a casual weekend, it can be great to have a notebook handy to jot down your passing thoughts.

 Making the leap to wearing shorts more frequently than denim or chinos can be a work in progress, even when it’s warm out. But grabbing a slim, stylish pair in a neutral color allows you to pair them easily with essentials you’d also rock with classic denim — like a short-sleeve shirt, a casual watch and loafers, for example. And when you take the approach that khaki shorts can work with everything from a T-shirt to a classic Oxford shirt, that opens another world of possibilities (heading to the office for a half-day? Try out shorts with a blazer — perhaps).  Plus, keeping things affordable and simple helps when finding out the pair that’s best for you can help  a great deal. Are you on board yet? Good. For more tips on how to style shorts this summer, head on over to my Instagram, or jump on over to Twitter if you’ve got other summer shorts picks.

Frank & Oak



  1. […] From the brand’s classic Harrington jackets to slim chinos, Ben Sherman specializes in classic pieces with a dash of mod, British edge.  This slim chambray shirt uses a nice medium blue color that would look right at home with slim, American-made chinos and brown chukka boots at the office, while also blending in nicely with, say, a first date ensemble.  It’s fairly priced considering the quality and history of the brand, and it’ll work just as well this coming winter under a slim cardigan as it will come spring time with your favorite pair of shorts. […]


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