6 MEN'S SUMMER DRESSING TIPS

Every guy has been there. He takes an interest in dressing better, joyously begins wearing cotton oxfords and selvedge denim. He learns the rakishness of layering with sweaters and outerwear. Then something unforeseen and terrible happens. Summer comes.Dressing well in the heat can feel so intimidating it seems impossible. As the rising mercury steals away our layers and textures and multitude of fabrics our advances in personal style come to a grinding halt. How can you dress well whenfirst and foremost you have to dress to stay comfortable? How can you build multiple outfits if the only items you can wear are shirts, shorts, and shoes?The secret, as with most of men’s style, is in the details. The following 15 items can be mixed and matched in endless combinations ensuring your sartorial skill doesn’t take a 4 month summer at the beach.1. The Polo That FitsYou’re no stranger to the polo shirt, also known as a golf shirt or tennis shirt. Your mom had been dressing you in these for as long as you’ve been fit to go out in public. You’ve spent your life seeing middle-aged guys wear these tucked into dress pants. And you’ve probably eschewed them as you’ve started caring about your personal style, assuming they’re for prep school kids and old guys on the golf course.And, if you’re basing that on what you’ve seen other guys doing, you’d be right.But the reality is the polo shirt can be one of the sharpest and most versatile shirts inyour wardrobe if you focus on getting the fit right.The polo actually has a fascinating history. In the early days of tennis, players (unfortunately) had to wear a full on regalia while on the court. Long sleeved button up shirts, ties, and flannel trousers(!?). As with all great change, it took a trailblazer to finally bring some sense to tennis attire. René Lacoste, seven-time Grand Slam champion, got fed up with how impractical and uncomfortable the uniform was and designed a short sleeve, knit pique cotton shirt with a collar and placket, and a “tennis tail” – a shirttail that was longer in the back to keep it from untucking. Lacoste first debuted his shirt atthe 1926 US Open, and in 1927 began sewing a crocodile patch on the left chest after journalists began referring to him as “The Crocodile.” After retiring in 1933, Lacoste went full-press into clothing merchandising.By the time Ralph Lauren showcased his polo shirt as a central figure in his new “Polo” line in 1972, the shirt became standard casual menswear.The secret, though, to not looking like an old man is to focus on the fit details. I’m not prescribing a “tight” shirt, a proper fitting polo based on the guidelines below will have any gentleman, regardless of weight or shape looking sharp.Polo bySt. John’s Bay, $10A common mistake young guys make is trying to size down to achieve proper proportions which can lead to a shirt with some of the details right but is overall too small. Look for a different brand, fit, or consider cheap alterations by a tailor. I also personally avoid tucking in my polos in all but the most business casual environments, in which case I would opt for a tucked in button up instead.Polo:Uniqlo, $18| Shorts:J.Crew Factory,$25| Shoes:Sperry, $882. The Not Pique PoloMichael Bastian for Uniqlo, $18When an outfit is limited to only a shirt, belt, shorts, watch, and shoes, it’s easy to get caught in an uninteresting, boring loop that makes you feel like you’re a different Big Box sales associate, depending on the color of the day. To counteract the negative ill-fitting look imparted on us by two decades of corporate uniforms we have to hammer in hard on the details.The smooth jersey polo shown here, a partof theMichael Bastian Collection for Uniqlo, plays with almost every detail. First, the smooth cotton versus the textureof a pique polo can have a surprising dual effect. If pairing with casual shorts and tennis shoes the smooth cotton can play like a t-shirt, tapping into the overall casualness. However, paired with slim, dressier shorts and penny loafers, a smooth cotton shirt now enhances the dressiness in a way a pique polo can’t.The collar, placket, and sleeve trim are contrasting colors, the shirt has a striped pattern, and the pocket has a button tab, all very unique details that take this look from boring polo and shorts to something that creates dimension with texture and color.3. The Fitted Flat Front Short in Multiple ColorsJ.Crew 9″ Gramercy, $25If you’re only going to buy one item on thislist, it’s the fitted flat front short. So many guys are still stuck wearing baggy, long cargo shorts from the likes of American Eagle and it’s the single biggest thing holding them back with their smart summer style.I included the baggy cargo short on my list of11 Out of Style Trends You Should PhaseOut of Your Wardrobethree years ago, and they were already YEARS out of style at that point. Yet, I still receive comments on that article from guys who refuse to let go of this 90’s style staple. Look, I get it – if you carry a ton of crap with you and you need the cargo space, have at it, function over form. But if you’re actively trying to dress well for summer events, they’ve got to go.Shorts have become slimmer and higher for well over a decade. And while there areplenty that are too high and too tight as you start approaching the fashion end of the style spectrum, there is a great middle ground that will give you a fitted silhouette without compromising comfort or showingtoo much leg. Don’t be afraid of seeing an inch to two inches of leg above your knee cap: It creates a more put-together, intentional look. When done correctly, it won’t look too tight or too short.Shorts come in different inseams these days, take a few pairs in the 7-9 inch regionto the fitting room and see what works with your body. If you’ve got monster quads, many slimmer models may not fit you; that doesn’t mean you default to baggy shorts that don’t fit, it means you find a different brand, or consider having them slimmed by a tailor. The cost of that, especially when buying affordable shorts in the $15-$30 range would be negligible – another $10-$15 at most. But what is the result? Crazy-good fitting shorts that you’ll be able to wear for multiple seasons.Once you find some that fit, go hog wild and buy them in multiple colors. Again, with a limited number of items in our getups, any difference in detail, be it color or pattern, will create a drastically different look paired with the same shirt and shoes. This year as I was preparing forthe summer season I picked up five pairs of J.Crew Factory shorts in the Gramercy fit, which have a 9” inseam, while they were on sale for $25 each. J.Crew Factory would be a great place to start, as they offer 4 different inseam lengths:11” Rivington,9” Gramercy,7” Reade, and5” Varick.4. The Boat ShoeSperry Top-Sider, $88Invented in the early twentieth century so sailors, would, you know, not slip and die while navigating a slippery boat deck, the boat shoe rose to sartorial prominence during the nation’s obsession with New England Prep style in the 1960’s. Once the domain of old men, or d-bags, or old men d-bags, the boat shoe has been within the everyman’s style for over 30 years, so don’t be afraid of them. No one is going to call you Mr. Harvard if you wear them, they’re going to call you that annoying guy who is always so well-dressed.The boat shoe is the single most importantpiece of footwear for summer style. Wear it casually with a t-shirt or dress it up with slim fit chinos (#12) and a button up shirt. They’re perfectly acceptable footwear in most summerbusiness casualsettings, and definitely my go-to for any summer date or jaunt. Once you’ve trekked around in them for a week or two they mold to your feet and become beyond buttery comfortable. Make sure you always wear them sockless. In this domain, they’re being worn the same way as sandals, and Iknow you know that you should never wear socks with sandals.Our pick is the original, the Sperry Top-Sider, readmy full writeup on them and how to wear them sockless comfortably here.Linen shirt:J.Crew Factory, $65| Watch:Timex, $45 (Similar) | Shorts:Ministry of Supply,