I’m still kind of against it – I’ve always felt gym clothes should be reserved for the gym, but I’m warming up to the idea that you can dress up sweats.

Sportin’ Sporty Sportswear a fairly new concept, and not all of the wrinkles have been ironed out, but we’re getting there. I’m still no fan of white athletic shoes with power suits, and I doubt anyone who is serious about their style would commit such a grievous offense. Letterman jackets with dress shirts and slacks is a look I’d take into consideration. Probably the first rule to this style of dress would be, quality athletic apparel only,


I’m not saying that Hanes doesn’t make a quality tee, but if you’re going to go this route, invest a little doe on the look. Designers such as Marc Jacobs and Michael Bastian have hopped on this trend and are currently offering their take on athletic gear.

Dolce and Gabanna offer a pair of black cotton track pants with a single stripe adorned with random words such as #family, #selfie, etc. up the leg. Pairing these with a black tuxedo jacket would send a message to the masses.

Speaking of the jacket, you’re wearing cotton or cotton blend sweatpants and a pristine and pressed blazer would look out of place. It would be more cohesive to stick with an unconstructed cotton blazer rather than a wool one.

I know this is going to sound like overkill, but unless your sweatpants fit you like a glove off the rack, get them tailored. They should be fitted with the leg and should not be bunched up at the ankle. Elasticized cuffs are going to work best as long as your pants are the same length as your leg or at least close.

Hoodie with blazers is another concept I had a hard time wrapping my head around, but I don’t make the rules, only report them. However, once my initial disgust pasts, I began to like the look.


If you were appalled that you New Balance sneakers were close to $200, try paying over $1,000 for Givenchy Trail Sneakers or even $500 for a pair of Giuseppe Zanotti red high tops. Athletic shoes have come a long way from the gym, and the right couple is entirely acceptable with slacks and a blazer or even a suit – the key words being ‘the right pair.’

There are now a plethora of designer sneakers to choose from. However, if you don’t want to spend or have the cash to blow on high-end kicks, Sketchers, Cole Haan, and Saucony Kinvara have proper shoes that won’t clean you out. There is nothing wrong with sports brands like Nike or Adidas, but you’re not going to the gym right now, don’t dress like it.

Caps have a place for your casual wear, and again, only the right ones will be acceptable. I have three Hugo Boss hats in different colors. The logo is tiny but tastefully noticeable, and that is what you should look for. If you are going high end, don’t be ostentatious about it. Small logos say a helluva lot more than huge ones. No head to toe logos is one rule you should abide by regardless of how much you are spending.

Sport team logos should be reserved for game day and caps with sporting brand logos should be worn to the gym. Please do not wear your designer cap backward unless you’re in high school; it looks ridiculous anyway – just my opinion.

Tracksuits always remind me of Goodfella’s, but they can be worn in a casual setting. You don’t need a $2,000 Brinoi tracksuits to be a part of the cool club, but don’t go cheap either. Lacoste and Polo have acceptable suits ranging from $150 to $275. While sporting brand logos might be useful for your workouts, they are not adequate for cocktails and appetizers.

Dust off your vinyl because currently, retro sportswear is in vogue. Even those dreadful short shorts that many of us older guys wore in gym class a few decades back have resurfaced. It’s not all bad though, and some very cool looks have a 70s vibe. Can you dig it? I knew that you could.

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