Men’s Style Q&A: Winter hat tips; Perfect leather jackets

The Sports Illustrated style Q&A returns for another week of tips on staying at the cutting edge of fashion. Today, we end your quest for a winter hat, guide you through buying a leather jacket, and make sure your wrist is as on point as the rest of your outfit.

The Sports Illustrated style Q&A returns for another week of tips on staying at the cutting edge of fashion. Today, we end your quest for a winter hat, guide you through buying a leather jacket, and make sure your wrist is as on point as the rest of your outfit. Look back through the previous installment of the guide here, and grab the DressForTheDay.com app so you can be dapper on the go. Dont forget to stop by the website as well for all the gear you could ever need.

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Q: I hate wearing jackets with hoods, so what kind of winter hats are effective but stylish? -Juan 

Hi Juan. Not a hood guy… we got it. Let’s explore the world of cold weather hats where fashion meets function. We’re starting with skull hats; so close to your skull (literally) of course they’ll keep you warm! For a polished look, check out this grey lined beanie from East Dane. For tech at its finest, Uniqlo’s Heattech Knitted Cap ranks high on our list! And for $10 a pop, why not get ‘em in every color? For some luxe options, check out this and this. Next, we’re heading outdoors where Elmer Fudd and Lumberjacks are taking all the right fashion risks. Check out our favorite winter hats in plaid & charcoal gray and this fur trapper hat. Lastly, we’re totally digging the wool cap meets baseball hat look. View our winning pick here. Hopefully our response was stylish & effective enough!

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Q: What's the one trendy item I should buy right now? -Dylan

Ok, Dylan, we swear this has nothing to do with your name (ehmm90210 heartthrob Dylan Mckay) but if we had to pick one item that every guy needs to have in his closet right now to stay trendy, it would be, drumroll….a leather jacket! Don’t worry, you’re not going to look like a Son of Anarchy gone wrong, with these options we hand-picked just for you. Bomber jacket: more subdued and best for the guy who’s more on the classic/conservative side when it comes to fashion. Another option and how to style it here. If brown is more your jam, this faux leather jacket from Levis is a heck of a deal. And finally, the moto jacket. It just doesn’t get more badass than this and you can get some streetstyle inspiration here. Whether it’s the subway, a Harley or a ‘Rari you’re riding, your street cred will definitely be in check.

Melodie Jeng/Getty Images

Q: I'm on the hunt for a new watch. I want something that will stay in fashion for a long time. What do you suggest? -Jackson

Hi Jackson! Sigh, how does one find the perfect timeless timepiece? Lucky for you we’ve been eyeing classic models for all budgets so you can keep that wrist game on point for decades to come. Luxury Splurge Option: check out this Cartier Stainless Steel & Alligator Strap for the traditional fat cat in you. Affordable Luxury Option: We love this statement making Movado Bold Gold IP Stainless Steel Watch. [Cue Godfather soundtrack.] Budget Friendly Option: Go black ops with Fossil’s discreet Chronograph Silicone Strap Watch. This baby matches everything, plus you’ll be ready to dominate in your call of duty zone. Bang For Your Buck Option: Interested in a classic look with a new twist? Here’s the Asos Wood Effect Sleek Watch we’re buying left, right and center. Now, if you want to play with the big boys and are looking to invest in a Rolex, AP or Patek Philippe, we’d love to introduce you to the wristguy. Tell him DFTD & Sports Illustrated sent you!

Steve Granitz/Getty Images

Q: A buddy of mine is having a destination wedding in Mexico. What do I wear to a beach wedding? -Sam

Hey there, Sam! Super jealous of your Mexican getaway, as we sit here in frigid temps and an impending snowstorm, but we’ll be nice and help you anyway (you owe us a marg; salt & on the rocks). Let’s start with the nucleus–the suit. Nothing screams beach wedding more than a khaki colored suit and the best part is you can wear them as separates come spring/summer. For a budget option, here’s a winner and if you’re splurging, you can’t go wrong here. Pair with a fun, printed pocket square like this, a fitted white-button down like this and some loafers like these (sockless, of course). Muy caliente!