Q. I’m a huge sneaker head—well over 150 pairs. I’m also a 47-year-old professional. Have I outgrown them? or is there a way to wear my beloved shoes and still look my age? —Roland, @baltotexan
A. Outgrown them? Absolutely not. If you’re passionate about your collection and want to show it off, you are allowed to, no matter how old you are. The trick to not looking as if you’re desperately trying to dress like you’re still 20 is to let the Jordans or Yeezys do most of the talking. Keep the rest of your look subdued, like this guy—think neutral colors, dark jeans, and minimal patterns that will let your soles shine.
Q. I’m a worked-out, broad-shouldered guy. If I buy a dress shirt that fits my arms, it’s always blousy around the waist. What do I do? —Kenneth, @kendorphins
A. The tough answer: Pay a visit to your tailor. He can take in the waist if your shirt fits in the arms and shoulders. The better answer: Find brands that make options cut for broader guys, like Hugo Boss’s “sharp fit” shirt. It shows off your work at the gym when you have to be at actual work.
Q. This year, I’m ditching my briefcase, since it’s falling apart. Should I just get a replacement? —Steven, @steven.fried
A. We’d suggest going instead for a hybrid. The way we move through the world now requires a durability that a leather briefcase can’t quite offer. Plus, thanks to our phones, we need both hands free most of the time. The solution: a muted backpack in strong technical nylon that can flip to briefcase mode as you glide into the office.
Q. I’m trying to reduce the size of my wardrobe. Is there a true three-season jacket I can Invest in? —Tyler, Pittsburgh, PA
A. Sure is. Behold the three-in-one parka. The outer shell acts as a rain and wind barrier. The fur zips off the hood when you’re no longer trekking through the tundra but still need a layer. And you can zip in the vest for added warmth or wear it on its own.
Q. What else is there besides a blazer that can keep me warm if I run out for a coffee—Zach, Columbus, OH
A. A thin wool blazer isn’t going to do much for you, warmthwise, in the winter months. And if you find yourself in a casual office, it can even look out of place. Which is why a neutral, minimalist fleece works best: It’s dressy in a best-dressed-at-a-start-up kind of way and still functions as a warm layer for coffee runs.
Q. Are there ideal pants for traveling? I want to be comfortable on the plane and still look good when I land. —Trey, @treygriley
A. Ah, the elusive dignity-maintaining travel pants. Instead of wearing sweatpants or scrunching into jeans, opt for pants with stretch and a flexible waist made for traveling with ease, like this pair from comfort king Mack Weldon.
Q. My New Year’s resolution is to start wearing a watch. What’s a good starting point? —Chris, Windsor, Ontario
A. If you’re not a regular watch wearer, you want to be sure you’re actually going to wear the thing before you put down big money for an expensive one. So grab a timepiece at an entry-level price. You’ll earn style points with a metal bracelet and bold face, and you’ll get used to regular wear without having to take out a second mortgage.