Rag & Bone Duke Shirt

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100% crisp cotton is a good choice for any season, and an even better one for comfort layering. Toss on a short-sleeve tee with a button-front closure with old-boy appeal or a little prep school flavor, and you're more or less ready to go. If you're more the geek chic type, try wearing it with a grandpa cardigan and '40s style pair of slacks. Good shape comes easy with Rag & Bone. [$79 at...

Phillip Lim "Moorish" Print Shirt

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Like your favorite faded tee, but better. Because it's new of course: we found this Moorish Tee at Oak in sizes s-m-l, and it features a ton of our favorite looks for less. We've got the gradient dye gently faded to white at the hem, and best of all, that kind of ombre dye makes us think of summer. Super soft, and with a design that stretches from front to back, this shirt's whereabouts needs...

Diesel Seguron Shirt

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Apparently nerd chic is back (or never went anywhere), if this Diesel shirt at Revolve has anything to say about it. Carefully crafted seams along a stylish yoke are the perfect touches to a ride 'em cowboy shirt with a little bit of library flavor cooked right in. 100% cotton makes this one all-season appropriate, which is good because you'd probably wear it all the time, anyway. Front breast...

J. Lindeberg Chelsea Heather Grey Sweatshirt

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Hooded heavy cotton fleece is a great choice from J. Lindeberg, because you get all the comfort without any of the itch. Squeeze into 80% cotton plus poly when you're crashed on the couch, and then keep this on when you head out for sustenance. Make it loungewear, sleepwear, and streetwear: it's stylish enough to be all three. Available in M and XL from Ssense with tone-on-tone stitching and...

Distilled Glenhooded Shirt In Glen Plaid

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Gray isn't boring: the cut of this Distilled Glenhooded Shirt from Revolve supersedes any drabness here! 99% cotton and 1% Spandex blend gives you a little stretch and warmth, and when you put on the hood, you'll be toasty 'til spring. But it's not just the practicality factor which makes this piece exciting-- the Distilled brand is dedicated to making "people stop and think by inserting...

s2vs Plaid Flannel Shirt

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Plaid flannel! We're doing our best to stay in a spring-like frame of mind, but the truth of the matter is that we're still pretty darn cold. This s2vs Plaid Flannel from oak is a fair compromise, and a darn stylish one at that. Traditional details skim the lumberjack side of things, but a colorway in deep navy with copper accents gets more modern. Bias front patch pocket and center back...

Unconditional Drape Neck J Shirt

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This is one silhouette that we might need to adopt when our wardrobes get stale: OakNYC's a perfect place to check out shirts with more daring male styles like this asymmetrically draped cowlneck top. Pull one on in charcoal and black like this (sadly out of stock) sweater as you wait for the thaw-- and in blends like soft merino wool, cashmere, and even silk. Good with slim trousers (not...

Hood by Air Eat the Children Cowlneck

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Hood by Air's "Eat the Children" sweatshirt might have a name capable of giving me nightmares, but the design (and price) is stuff of style dreams. Available at Revolve, this casual sweatshirt features a pretty traditional silhouette until you pan up to the neck-- that's where things get interesting. Multiple snap button decorations adorn a high, rumpled neckline that looks cozy but tough. ...

Diesel Trascina

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No square 'n' baggy t-shirts here. Diesel selections are usually available in a wide range of fitted shapes, and this one is no exception. Scoop up this shapely (but manly) v-neck in a modern look that doesn't disappoint with jeans. 100% cotton jersey with bold print detailing makes this a smart buy: wear it now with a hoodie or cardigan sweater, and then strip off the other layers to let it...

Complex Geometries Cotton Square Hood Tee

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This jersey square hood tee combines two worlds that we really love, fashionably-speaking: short sleeves and hoodies. Oak NYC brings us a snowy white overshirt with healthy drape (good for throwing on over tanks or your odd beater), and it's available in XS-L right now. 100% cotton and going fast, so I recommend you make your move right away. [$96 at oak]

Orisue Aldred Hooded Button-Up

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80s purple gives us a great shirt that'll fit right in the giveaway range, and it's a pretty winter-worthy piece. Wear it under lighter-weight jackets so you can pull the hood up for outdoors meandering. Small chest patch pockets will only accommodate something little, which means you might also have to employ a messenger or other bag. Small price to pay. Sizes s-xl. [$70 at 80s...

Whyred Shinnosuke Dark Navy Hoodie

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Hate messing up your hair when you pull on a hoodie, and hate admitting it, too? Get a look at a this raglan hoodie with a contrast asymmetrical zip, which is way more practical than at first glance. The look of a hoodie with the ease of a front-zip sweatshirt. . . we could very well be in casual fashion heaven right nows and not even know it! 100% cotton. [$165 at ssense]

Lee Hawk 2-Button Shirt

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Fun, red plaid is a great choice for this time of year, wouldn't you say? Disguise your hopelessly festive side with a funky selection we found at Karmaloop that features a checkerboard pattern all over and a logo label at the side seam. Available only in this rich burgundy color; sizes small to extra-large. [$59 at karmaloop]

Men's Classic Geek Dress Shirt

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A tie without the tie: save yourself some time, lazies! All you need to do is sling on this white-and-black combination dress shirt for a geeky vibe in classic colors. Flap pockets make for a comfortable stowaway place for daily stuff sans manbag, and then you can just unload them for the night out. Available in s-xl. [$70 at 80spurple]

Mike & Chris Cadison Black Hoodie

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A black hoodie with unusual shape is an essential buy, so if you haven't gotten one yet, now's your chance. A long sleeve zip closure is accented with foldover plackets (and secured with buttons to keep everything in place). Tone-on-tone stitching (black) vaults this piece into the Serious Style category. 80/30 cotton-poly, sizes s-m-l. [$253 at ssense]

WESC Croatia Cashmere Sweater

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100% cashmere is a must-buy, but after a while, it gets pretty tiring looking at all the boring (solid) colors of the rainbow. This Wesc sweater combines the superior warmth of cashmere with an urban flair: graphic designs rip down both sleeves and are juxtaposed against a solid body. It's fun looking at it, and it's even better wearing it. Available in sizes s, l. [$286 at revolve]

Wesc Men's Logo Darkness Hoodie

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A fun hoodie never goes out of style, and this graphic version has the wow power to stand alone with jeans. If you don't have the time to mix and match, keep this piece close and forget about the finer details. Looks good with a fashion-forward hat because it's more stylish than the trad hoodie. Available in sizes S-XL. [$90 at 80spurple]

Cardboard Robot Men's Deer Hoodie

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All animal, but no animal: this hoodie is a cool play on what PETA hates. A fur-lined hood is an amazing investment for cold weather and makes a lot of jackets more wearable, while the antler designs on the front are just a touch ironic. Stuff your hands in your pockets for a casual cool look, and conveniently forget where you bought it when the complements come rolling in. S-XL. [$125 at 80s...

Endovanera Crimson Black Button Hoodie

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Hate scarves? Keep your neck toasty the old-fashioned way with this high-button hoodie from Endovanera. Sleeve cuffs come complete with little thumb holes to maximum wrist warmth and cozy comfort, and that half-button high placket at the neck will come in handy when you are feeling chilly. Available in sizes S or XL. [$242 at ssense]

Gar De Handcuff Vest

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Never thought you'd find yourself with an urge for a leather vest? Yeah, me neither. This piece was designed exclusively for hip boutique Oak and simply radiates their devil-may-care, haute vibe. Lined in ecru, with a tapering front that ends at a diagonal closure. Snap it up in s-m-l, and adjust it at the side straps for a perfect fit. [$432 at oak]