The Tricky Art of Dressing Up a T-Shirt, and More Style Dilemmas Solved

We tackle your latest round of fashion quandaries.

Photo: Everett Collection

Crockett lays down the law: The more copious the pleats, the deeper the scoop neck.

As my wardrobe has matured, I find it increasingly hard to decide when to wear a nice T-shirt. I have many with simple logos or mature and tasteful abstractions, distressing, and fine fabrications. However, what I have lost is a handle on when wearing them is appropriate and how best to place them into an outfit. Are T-shirts only for wear with jeans in the most casual of settings? Or is there a respectable way to dress them up?
The “if you have to ask” rule is a good one to follow here. Listen to your gut. It’s telling you that you’ve now reached a point in your life and in the evolution of your wardrobe where T-shirts—yep, even those adorned with tasteful abstractions—are best saved for casual circumstances. That said, if your T-shirt collection represents a high level of what economists called “sunk costs” and you feel compelled to get your money’s worth, don’t be timid. Pair that distressed tee with a sharply tailored suit, along the lines of what Jude Law has been doing lately (save the Sonny Crockett look for October 31st). As a side note, if you’re in the market for a suit worthy of Mr. Law suit, keep an eye out for our next  Martin Greenfield sale, which goes live later this month.

Can you create a section in here “wooing the ladies”? I need some gift ideas for my girlfriend’s birthday. it would also help for men to know the rules and regs of gentlemenly dating….
Love that idea, though we may want to work on the name. Maybe something a tad more upmarket, like “Baggin’ the babes”? Anyway, as for your girlfriend’s birthday, try Gilt. I know, I know, I’m biased. But I’m also right. The Gilt women’s buyers are pros at choosing only the best brands, so if you find something you like, odds are your girlfriend will feel the same. You can shop the daily email by brand, or scan the “Gifts” section if you want to browse by category or occasion. Either way, I’d recommend resisting the urge to treat Gilt prices as an opportunity to save a few bucks, and instead look at those discounts as a chance to trade up in quality for the same price. (Something tells me your gf would agree.) (Oh, and if you’re thinking about buying jewelry, read our guide here.)

As a 28-year-old guy who’s finally transitioning from college-wear to a more adult—albeit still casual—wardrobe I just wanted to say thanks for providing practical, straightforward, and humorous advice along the way. I do have one question, though: While I know I look good in a suit, I just don’t like business/formal wear. I realize all workplaces vary, but as a general rule is it better to suck it up and “play the game” as a young professional, wearing the expected suit and tie, or can I still command respect with stylish jeans and a sportcoat? Does the fact I’m in Seattle, where life is more casual in general, make a difference? Thanks, guys! Jonathan
Thank you for the kind words–and great question.  Ten to fifteen years ago, most 28-year-olds were desperately plotting ways to stave off the arrival of adulthood, not strategizing how to greet its arrival with style. If you’re not suit guy, by all means skip the pinstripes, but put in some effort. A blazer and chinos or dark jeans should more than suffice, especially if you pay close attention to fit, invest in quality footwear (a true sign of adulthood in my book), and accessorize subtly but confidently (also: don’t use the word “accessorize”). Among the many reasons a man chooses to dress well—wooing the ladies, good old fashioned vanity, etc.—the most overlooked is this: respect for your surroundings and those around you. If that’s playing the game, well, I got next.

We can’t do this without real questions from real guys like you. Send your latest style quandary to [email protected] and we’ll do our best to cook up a solution, either via email or published on the site.

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  1. Christian says:

    Crockett. Wow. Brings it all back…

    I’m in the business of T-Shirt customisation (with TGraffi) and would just like to add that tees are one of the most versatile items in the world, ever, and there’s plenty of room for a ton of creativity and trying stuff out.

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