Avery,
As a young professional, I find the concept of casual Fridays nebulous. In the summertime, are shorts ever OK? If so, are “boat shoes” acceptable footwear? What about golf shirts instead of button downs? So many questions…HELP!!

I feel as though I must applaud you for your excellent word choice. I think this is the first time I’ve ever seen the word “nebulous” outside the confines of a spelling bee. As for the rest of your question, however, why must “boat shoes” be inside “quotation marks”? Yes, sir, they are a very, very acceptable form of footwear, though your punctuation leads me to believe you may disagree.

Let me guess: you’re a 20-something with OK style, but a fear of even dipping a toe in the adventurous waters of men’s fashion. Don’t be ashamed, I can understand that. There is some truly frightening apparel out there.

But come on! You know how they say your youth is the time to experiment? Get your mind out of the gutter, I don’t mean it like THAT. I mean that a 20-something can pull of some more daring ensembles than a guy in his 30s, 40s or 50s. Plus, now is the time to establish your personal style and figure out exactly what your taste is. On top of all this, chicks love a guy who knows how to dress himself. If that isn’t incentive to improve your style, I don’t know what is.

So, to answer your question: casual Fridays are very vague and actually make me feel a teeny bit anxious. The term “casual Friday” belongs in the same category of oxymoronic fashion terms such as “dressy casual” and “cute Crocs.” I’m with you, man. This is tricky.

But you seem to be on the right track. Shorts are acceptable in the office, as long as they’re A) not cargo shorts or anything with more than five pockets B) well-fitting and not too long and C) paired with something business-y on top. When you’re wearing an article of clothing in a work setting that can double as casual-wear, you have to make sure the rest of your outfit looks professional. This is easy for guys, as you can pair your shorts with a nice button-down — tucked in and belted with the sleeves rolled up — or a lightweight crew or v-neck sweater. Before you protest, remember how freezing the office environment is in the summertime. It’s practically arctic.

As far are “golf shirts” go, I don’t really have an answer for that one. Mainly because I’m still a little unclear on what a golf shirt is, but I feel like I don’t like it (note my use of quotation marks). And since I just Googled the term and it yielded pages upon pages of the ugliest polo shirts/short-sleeved button-downs I’ve ever seen, I’m going to now give a resounding “NO” to your question about golf shirts.

I hope your feelings aren’t too hurt by my harsh criticisms of what I’m just assuming is your personal style. This was all meant to be motivating, but I may have crossed the line into bullying. Regardless, I hope you start dressing like the man candy you probably are and get the whole office drooling. Best of luck, bro.

I am a 47 year old male, carrying more weight than I want, professional who is more comfortable dressing up than dressing down. What are the best looks for the summer that are age appropriate?

I love when men would rather dress up than dress down. It’s harder than you may think to find a guy who prefers slacks to gym shorts and who would rather don a sport coat than a sweatshirt. Plus, if you’re carrying extra weight, you likely look far better in professional apparel than casual wear. So even though you may have questions, don’t worry: you’re already on the right track.

When I have a specific fashion problem such as yours, it usually helps me to think of a well-dressed individual and check out how they deal with the issue. Essentially, I find a style icon and a take a cue from her wardrobe choices. Lucky for you, I’ve chosen your style icons for you: Alec Baldwin, a heavier-set middle-aged male who always dresses up, and George Clooney in his “Syriana” phase, when he gained extra weight then lost it all after the film wrapped. Both men dress well to accommodate their body types and both men give you unique answers to your question.

If you go the Alec Baldwin route, getting dressed is pretty easy. Mr. Baldwin always wears a sport coat and shirt — simple yet classic. The trick for looking as good as he does, however, is to make sure all your clothes are perfectly tailored. Most people truly underestimate the power of a good tailoring job but you, sir, should not. Just because your heavier-set doesn’t mean your clothes have to be shapeless. Pants should always fit you perfectly, coats should be snug but comfortable across the shoulders and shirts should accommodate extra weight around the middle, but shouldn’t be too loose.

If you check out Alec, you’ll notice he sticks to a classic combination of a white shirt with the top few buttons unbuttoned and a dark coat and that look will work for you all year round. It works for him, anyway — he just married a 28-year-old yoga instructor.

If you opt for George Clooney’s route, which — let’s be honest — is what most sane men would like to resemble, your look will say “I live in Italy and lounge on yachts, but also have time to work for the UN.” That doesn’t sound bad to me.

Clooney’s style, even at his heaviest, is relaxed and untucked, yet dapper at the same time. To emulate it, opt for white linen shirts paired with khakis or summer suits in light gray or tan. Even if you prefer to dress up, a pair of khakis and an untucked white shirt with loafers is by no means casual. It may seem overly simple, but I promise you, you’ll look great.

If you have any questions for Avery, don’t hesitate to ask them here!

(Header photo courtesy of Flickr / Bayliss.)