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    10 Signs It's Time To Update Your Wardrobe

    Fall is coming, you ragamuffin. All you need are a few key pieces to go from generic to gent.

    1. You can picture Larry David wearing your sneakers.

    Some people can pull off "Cool Dad Style." Chances are, you are not one of them.

    Instead: trade your staid cushioned insoles for a quality pair of brown leather boots or oxfords.

    Peggy Wang/BuzzFeed

    Chukkas, Red Wings, those hiking boots with the metal lace clips — whatever you pick, know that they require even less thought than your go-to sneakers because they go with EVERYTHING.

    Clockwise starting from the upper left: Closet Freaks Blog | $162 from ASOS | Red Wings Boots | Closet Freaks Blog | $355 from Russell Moccasin | Best Gear

    2. Your v-neck sweaters are moth-eaten and threadbare.

    Helpful hint: clothing from the Old Navy sale rack were not meant to last a lifetime.

    Instead: rely on a chunky fisherman sweater for warmth.

    Peggy Wang/BuzzFeed

    You will be cuddly! But also manly.

    Helpful hint: LL Bean makes great fisherman sweaters, and if you're on the small side, you might be lucky enough to save some $$ and shop in the boys' section.

    Clockwise starting from the upper left: Scotch & Soda | $109 from Orvis | $139 from LL Bean | $199 from APC | $235 from Zady | Gwaltney's Flickr

    3. Your laptop bag is a relic from the dot-com bubble era.

    Your laptop has moved on, yet your case is still the Windows 98 of messenger bags.

    Instead: embrace the manbag, literally.

    Peggy Wang/BuzzFeed

    Sure, you might miss the padded laptop compartment and the patented velcro Bluetooth headset holder. But these bags look so good that they'll even make your cargo shorts look sexy (don't wear cargo shorts).

    Clockwise starting from the upper left: Men of Habit | $415 by Makr | $159 from Zara | $95 from American Apparel | $248 by Filson | $280 from Makr

    4. The coolest feature on your current wristwatch is Indiglo.

    You might also be lucky enough to have a pointless alarm and the ability to withstand the pressure of 100 meters of water.

    Instead: invest in a leather band watch.

    Peggy Wang/BuzzFeed

    You'll have to start taking your watch off before showers but SACRIFICE. No pain no gain, form over function, etc. etc.

    On a sidenote, Timex also makes very nice watches with classy leather bands. So you might not have to lose the Indiglo after all!

    Clockwise starting from the upper left: Indie GoGo | $100 by Komono | $150 from Amazon | $115 from I Love Ugly | $215 from The Ghostly Store | $390 from Uniform Wares

    5. You're frequently swimming in "blousy" work shirts.

    Although don't get me wrong — your roomy Chandler-channeling shirt is due to make an ironic comeback at any moment.

    Instead: do your figure a favor with a slim-cut button-down shirt.

    Peggy Wang/BuzzFeed

    You don't even have to tuck it in! It still looks good. J. Crew and Uniqlo are good, less expensive options.

    Clockwise starting from the upper left: Mens Fashion World | $139 from American Apparel | $98 from Outlier | $33 from Asos | $69.50 from J. Crew

    And for crissakes, get a nice belt to go with them.

    $105 from Barneys

    $80 from Union Made.

    Tanner Goods makes beautiful leather belts that are just thin enough, with interest complementing metal details.

    6. You own one scarf, and it's made out of polar fleece.

    Once an item of clothing becomes an "easy DIY project you can make in under an hour!" it's time to move on.

    Instead: throw on a fringed scarf.

    Peggy Wang/BuzzFeed

    No, really THROW IT ON. You will automatically achieve the perfect degree of dishevel. This single important accessory builds character like no other item of clothing can do.

    Clockwise starting from the upper left: $150 from Acne | The Classy Issue | $30 from Zara | $28 from Need Supply | $16 from Asos | $14 from Maxnina | $55 from Norse Projects

    7. The only socks you own came in a "value pack."

    "The wifebeater of socks."

    Instead: dare to wear socks in a bright color or interesting pattern.

    Peggy Wang/BuzzFeed

    They're really not as foppish and dandy as you might think. That tiny sliver of detail that peeks out below the pant break when you sit down is PURE DELIGHT and nothing else.

    Clockwise from the upper left: A Gentleman's mentality | $3 from Chup | $18.50 from Hemp and Company | $8 from Asos | $12 from Steven Alan | $22.50 by Paul Smith

    8. Your idea of "adventure" is leaving BOTH buttons of your tried-and-true polo shirt undone.

    Your polo shirts are fine for summer, but hardly work as a "layering piece" for autumn.

    Instead: come to terms with the universal truth that a plain striped tee goes under everything, from hoodies to sportcoats to sweaters.

    Peggy Wang/BuzzFeed

    9. You're still trying to get mileage out of a $10 pair of Urban Outfitters wayfarers.

    Instead of being a protective accessory for your eyes, they've really just become a symbol of a thing in your life you managed not to lose.

    Instead: shell out for nice pair of tortoiseshell-rimmed sunglasses.

    Peggy Wang/BuzzFeed

    10. Your jeans still have whiskers on them.

    While Diesel was once a hot international men's fashion brand in the early to mid 2000's, it's time to let go of those prized jeans you once spent upwards of $200 on. They're unnatural. No superhuman could possibly create that many crease marks around their crotch area.

    Instead: try a stiff pair of slim-cut dark wash jeans.

    Peggy Wang/BuzzFeed

    Skinny jeans are a thing of the past, and the form has settled on a nice, sensible, slightly-tapered cut. It's practically Hegelian, so let's just be thankful we are living in a new era.

    Starting from the left: $135 from Need Supply | $105 from Williamsburg Garment Company | $155 from J Crew

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