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.
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.
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.
The Style Guide 
[…] overlooked from time to time, what with plenty of warm-weather #OOTD options out there, be they stylish shorts or slim light wash denim. Yet, dressier looks are still in order for most us throughout the week. […]
[…] use reminders about things like proper fit, and this polo makes it easy. It’s wearable with slim shorts or tan chinos, and it doesn’t look out of place when worn in an even more laidback fashion […]
[…] point in the season — can be a bit tricky. Perhaps you feel you’ve exhausted all the ways to wear shorts in the summer that you can think of, or maybe you’ve even tired of styling linen pants in the heat. But, […]
[…] approach it like a style upgrade. On the other hand, it would also be agreeable to rock a slim striped shirt in case after-beach drinks at a nice restaurant are in the mix (that’s also where refined […]
[…] The Hat: Huckberry Explorer’s Cap, $39.98 — Swapping out your athletic logo ballcap for a more subtle, refined hat is a solid style upgrade that makes a difference — this is the perfect cap to wear for the occasion (note the blue-and-white color) and it can even dress down a classic polo and chino shorts. […]
[…] really working that neutral color angle?). Of course, you can easily wear it sans jacket with your favorite pair of chino shorts the rest of the […]
[…] bit chilly in early fall. And right now, you should definitely break them out with everything from slim chino shorts to light wash denim. The only doubts you should have are whether to buy these in White, Navy […]
[…] (at least for your Style Guide author) about stowing away certain #menswear pieces — like lightweight summer shorts or a short-sleeve chambray shirt — for more durable, rugged and hard-wearing items. However, […]
[…] Oh, and if the weather is still balmy in your neck of the woods? Scroll through this warm-weather style suggestion. Now, back to the matter at hand. Your fall explorations might seem more casual — and thus, […]
[…] 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. […]
[…] polo and classic tan chinos every chance you get — and know that they’ll work with slim chino shorts and a patterned short-sleeve shirt on weekends just as well as the weekday. And if you feel like […]