Wear it Well: Raiding Matthew's Closet

Wear it Well: Raiding Matthew’s Closet

Meet Chubstr's newest contributor, Matthew Simko
Meet Chubstr’s newest contributor, Matthew Simko

Today marks the first installment of Wear it Well, a feature that helps readers create interesting looks from clothing they already have in their closets. New contributor, Matthew Simko kicks things off by creating a few outfits from his own closet, while offering tips that any guy will find useful.

We all have those “what the heck am I going to wear with this?!” items in our closet. It’s usually something that caught our eye, was priced right, and that we just had to have, but we’re totally clueless as to how to wear it. That’s where Chubstr comes in. We’ll be taking user submissions of “problem clothing” and finding the perfect, and even unexpected items to pair them with.

First up, we take these cream-colored, lobster-embroidered shorts. They were purchased at the J.Crew outlet for $9.99 (about 85% off). They look cool, they’re a little different, but they’ve been sitting in a drawer for 3 years. We could go totally traditional with these shorts (Like Nordstrom’s 4 Shorts for Summer guide says to do), but we’re not much for rules around here so let’s try something with a twist before we head down the traditional route.

Matthew's Tee & Shorts Combo
Matthew’s Tee & Shorts Combo

These shorts really pop with a vintage inspired t-shirt or thrift store find—the more out of the box, the better—and you can find some great tees at Threadless.com in sizes up to 3x. The t-shirt we’ve chosen is at the opposite end of the style spectrum, but that’s why it works. It’s unexpected, a little edgy, but still captures the laid back easiness of the short’s “east coast roots.”

Pairing one style with another, “walking the line” as we like to call it, is a trend that’s being embraced more and more. And it’s especially great for us big guys, as we’re often forced to buy clothing from stores that cater to different styles. Think different on this one, it’s what really makes the outfit come to life. For shoes, try a slip-on like TOMS or a classic solid color canvas sneaker from Vans. If accessories are your thing, a big chunky, solid-color watch (this one is Nordstrom, $19.50) will add some visual interest.

Traditional, yet bold
Traditional, yet bold

Now, if you want to go the traditional route with these shorts, make sure to go bold! A pink, or any brightly-colored Oxford (Macys & Macys.com. Sizes up to 4X) tucked in with a Nantucket belt (Vineyard Vines. Up to size XXL & 44) is the ultimate in summer prep.

Remember—when styling a preppy look, don’t hold back. The idea here is a layered, pieced together, laid back look. Throw on a pair of boat shoes (Sperry.com) or flip flops to complete this look. Accessories for this one should be coastal-inspired, a sailor knot bracelet and a simple watch with a slip through interchangeable band (Timex. $45). Getting chilly at the beach at night? A classic navy blazer (try the sleeves cuffed up) will take the chill off while keeping the look in tact.

Dressing things up a bit
Dressing things up a bit

The first outfit is perfect for the farmer’s market on Sunday or running errands any day of the week, while the second would fit in perfectly at any New England beach side clam bake, or on the Ferry to Nantucket for the weekend. Whichever you choose remember to wear it with confidence. That’s what really sells any look.

As we said, we’d like to help you tackle some of the “problem” items in your wardrobes. If you’ve got pieces of clothing you love, but can’t quite figure out what to pair them with, take a picture—a clear one that shows as much of the article of clothing in as much detail as possible—and submit it to us. We’ll find some great options to help you get more mileage out of the clothes you already own.

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