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Last updated on September 19th, 2017

The following is a guest article from Megan at Style Girlfriend.

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Guys, it’s official; fall is happening. That means, it’s time to stow away those summer clothes and get ready to start bundling up in style.

Even if you don’t physically swap out your closet’s contents from warm weather clothes to cool, (and back again in spring), you’ll at the very least be digging sweaters out from the back of your drawers, and piling wool-lined pants on top of your shorts and swim trunks.

Here at Style Girlfriend, we’re very excited for autumn.

Why? Well, first of all, we love a guy in a layered-up look. Piling on more colors and textures to an outfit always adds interest. And second, it means we get to help guys go shopping!

The best part? We’re not insisting you need a whole new wardrobe; a few key updates are all you need to make your style feel totally fresh for fall. These quick hits will definitely make your style pop this season.

Fall Style Checklist

Below, the checklist you need for work and weekend this autumn:

click to enlarge (opens in new window)

Work

Check or windowpane shirt: You’ll never catch us claiming that gingham is over, but diversification in your shirting portfolio always yields positive returns. We love a windowpane because it feels like a bit of a throwback while still looking totally fresh for today.

Wine-colored chinos: Women love a man in brightly-colored pants, as it shows a level of confidence that not enough guys have these days, but it’s fall, so let’s be reasonable. Tuck the bright blue and salmon hues away for the season, and bust out bottoms in shades you’re likely to see at the Thanksgiving table.

Double-breasted suit: Hey, we didn’t promise you we wouldn’t be at least nudging you slightly out of your style comfort zone with this fall shopping list. While a double-breasted suit is definitely not for the faint of heart, it’s such a classy look that we think it’s time you got involved.

Chunky brogues: Consider these dress shoes the indie band you discovered two years ago and who are just now getting radio airtime. The chunky footwear style has been around a few seasons now in the “fashion” scene, but now, these shoes are going mainstream.

Rock them with a suit to work, and on the weekends with a rolled pant to show off the true heft of the sole. Wear socks with caution..a bold sock with a bold shoe can be a heck of a lot of look.

Chelsea boots in brown suede: Women love a man with confidence, and we’ll admit it – it takes a fair amount of confidence to wear a chelsea boot. Fear not, though, these shoes aren’t just for mod rockers anymore. And they’re definitely more versatile than you perhaps once thought.

Sure, the Beatles rocked theirs with skinny suits, but you can sport yours with slim jeans or khakis in a dark color (think army green or navy) that have some heft to ‘em.

Wear it well

A chunky brogue is the versatile statement piece that’s perfect for fall and winter. You can easily style a pair with your suit or dress them down with jeans for a dapper happy hour look.

Blazer: Hugh and Crye // Portfolio: Moore & Giles // Lapel pin: Hook & Albert // Socks: Bugatchi // Pocket Square: The Tie Bar

Weekend

Twill jeans in black: Obviously you’ve got plenty of standard navy-hued denim, but have you thought about breaking out from the typical jean pool? Look for high-grade Japanese cotton for a twill pant that offers a bit of stretch and retains its shape from day to night.

Your best bet is to opt for a pain in a shade close to the denim you’d wear anyway – blue, grey, or black (we like black). You’ll get the most use out of them.

Leather jacket with shearling collar: Is there anything more masculine than a leather jacket with a shearling collar? Maybe a bear smoking a pipe, wrapped in bacon. But that’s it.

If you already have a leather jacket in a moto or bomber style, this is your next purchase to round out your “cool guy outerwear collection” (yes, that’s a thing).

Try swapping a suit jacket for this tough topper: a date night kitted out in dress pants, a button-up, knit tie, and a leather jacket with some furry shearling she’s going to want to put her hands on immediately? Oooh, you can’t go wrong.

Striped tee: Sure, you’ve got white t-shirts, grey v-necks, and that boxy tee you got for free from that 5k you ran last summer, but what about one with a little more style? A striped tee in a heftier cotton looks great with jeans, khakis, and could even sub it in for a dress shirt the next time you suit up.

Crewneck grey sweatshirt: Athleisure is here to stay, but it’s not an excuse to look schlubby. Expand your sportswear horizons in a stylish way with a grey crewneck sweatshirt that you can dress up or down with ease.

Weekender watch: Does anyone actually need a watch anymore? No. But, for many men, it’s a fun way to show off personal style, and fall is as good a time as any to start marking time in a new way.

If you feel panic rising at the thought of keeping your phone off the table at dinner, start with something non-committal (ie, inexpensive) and switch out straps as often as you switch your Saturday night plans.

Navy chukka boot: We’d like to think most guys have their sneaker game on lock, so why not trade up your weekend footwear for a navy boot this autumn? A chukka boot isn’t so much a seasonal piece as a “Seriously you need this in your life forever” kind of piece; the navy is what takes things up a notch.

Wear it well

It’s always a good idea to round out your look with a classic statement piece. This rugged weekender should definitely be a mainstay in your watch collection so you can be on time for your next date…

Hat: Hippytree // Shave Kit: Harry’s // Belt: Arcade Belts // Wallet: Tight Wallet

Tell us…

What’s on your fall shopping list? We’d love to hear it in the comments below!