Personal Style

    Style Girlfriend’s Fall Essentials for Guys

    15th October 2013

    Quick. What are your top three wardrobe essentials this fall?  

    Don’t have an answer on the tip of your tongue? Then read on.


    Back in August, I partnered with Timberland to shoot fall’s must-haves for Esquire Magazine. Check out my good friend CB‘s fresh-to-death look in the November issue.

    When Timberland asked me to get involved, I couldn’t have been more excited. Why? Well, 1) Fall is not just my favorite season, but inarguably the best season (apple picking! pumpkin carving! cider drinking!), so helping you figure out what to wear as the weather turns cool was right up my alley.

    And 2) I knew I’d be putting you guys in good hands with the heritage brand. They definitely know how to make clothes and accessories you want to tromp through recently fallen leaves while wearing.

    So, what does the well-dressed man need for his wardrobe come fall weather? Easy. Just remember 1+1+1.


    • 1 piece of clothing: in this case, a timeless leather jacket
    • 1 accessory: a great, goes-with-everything watch


    • 1 shoe: a sturdy, stylish boot


    Leather Jacket:


    {Earthkeepers(R) Abington Leather Field Coat}


    style-girlfriend-timberland-esquire-watch{Campton Multifunctional Watch}

    A timepiece that’s a little oversize feels perfect for fall, as it won’t get swallowed up by chunky sweaters and extra layers. Besides, checking your phone for the time is so 2012.


    style-girlfriend-timberland-esquire-shoes{Earthkeepers(R) City Premium 6-inch side zip boot}

    Look, I’m from Wisconsin. You think I’m not going to namecheck durable boots as a fall essential? Even if you’re living in somewhere warm and sunny where all that’s crunching underfoot is fallen palm fronds, a great boot is a must. This pair of Timb’s ties together outdoor performance and style in one. You can dress yours up (with a grey suit, perhaps?) or down in jeans and a tee on the weekends.

    Tell me:

    What are your wardrobe essentials for fall?

    This post kindly brought to you by Timberland and Style Coalition. Opinions and Midwest pride are my own

    • ilyac

      While I don’t have a leather jacket, boots and a watch have been part of my wardrobe for a while. I have a Skagen watch as my go to. It’s very slim (oversized watches looks silly on me) and simple with a brown leather band so it can be dressed up or down, and a pair of simple brown Doc Marten boots I can do the same with. I would not wear the boots with a suit though, since they have a pretty thick sole, but they do look nice with a pair of chinos or something.

    • Joshua

      I live in Southern California and for this not-so-colder season, I would wear a cardigan every now and then underneath my sport jacket.

      I do want a pair of boots but the one I want (Allen Edmonds’ Dalton is just not within my budget currently.

    • Jim

      “Essential” gets thrown around a lot on style blogs, but these are all pretty strong choices. I would say that a leather jacket isn’t mandatory, just some kind of in-between jacket that’ll get you through a range of fall temperatures depending on your other layers: a military/field coat, a Barbour-type waxed cotton, or even something like a varsity jacket if you can pull it off (I can’t).

      Depending on how often you have the occasion to wear a sportcoat, tweeds are amazing and can usually be found at thrift stores in great condition. Herringbone and subtle plaid patters are my favorites, and because they’re the most casual sportcoats around, just throw them on like you would a regular jacket. It took me a while to get used to wearing a sportcoat as a functional garment rather than something I put on to look dressed up, but it helps that you can take it off at work or wherever you’re going if it feels a little stuffy.

      Also: Grey crew-neck sweatshirt. Swap one in for your hoodies and instantly look more put-together than your slob friends.

      • Style Girlfriend

        Oh my god, it’s like you’re reading my mind Jim…or my editorial calendar! Be on the lookout for a post on grey crewneck sweatshirts soon!!

    • average joe

      I bought the SG recommended Dr Scholl’s wingtip boots last year and will break them out in a few weeks down here in ATL

      • Style Girlfriend

        Niice! We want to see a pic when you finally bust ‘em out

    • TJ

      Can’t decide on 3.
      Boots (chucka or wingtips)
      Wool ties
      I also have an oversized shawl collar cardigan that I wear around the house.

      • Style Girlfriend

        All great picks. A wool tie is totally underrated as an essential but perfect for the season. Good call

        As for that shawl collar cardigan, why doesn’t that thing make it into the “outside the house” rotation?!

        • TJ

          It’s way to big on me. It was kinda big when I bought it but now that I’ve lost weight it is definitely too big. It’s my lounge around the house grandpa cardigan

          • Style Girlfriend

            So…time for a new one that fits, is what I’m hearing.

            • TJ

              Oh definitely. But I live in Florida now, and haven’t experience a fall/winter here, so I’m not sure how cold or rather less warm it will get here. Gotta feel it out and see how much fall clothing I’ll actually be able to wear.

        • Jon

          I’m with TJ. I also have a very warm shall collar sweater, complete with leather elbow patches and chunky toggle closures. It’s perfect for reading a book by the fire after the kids are in bed. When I got I, I knew specifically that it would be my after dinner/around the house-only garment. I love it and want it to last forever, so I take extra care of it.

    • Moe

      The essentials are Clarks boots, Flannel shirt, and a White shirt

      • Style Girlfriend

        So definitive of you! I love it

    • kellen owenby

      Since I live in GA, and it doesn’t get very cold until after Christmas, here are my fall essentials:

      brown leather desert boots (w/ colored laces)
      imogene+willie selvedge denim (barton slim fit)
      flannel shirts (j.crew, gap, vintage thrifted)
      denim jacket (levi’s)

      I’m pretty sure that’s about all I could ever need…

      • Style Girlfriend

        Love that your jean jacket is Levi’s – so authentic!

    • Lucas P

      Cords, denim jacket, and clarks boots are what I’ll be wearing this fall.

    • Jason W

      Would these boots transition OK to winter? Where I live it gets cold and dry (Saskatchewan).

      • Style Girlfriend

        I might go for a more durable winter boot, like a Sorel. These are more for fall and looking goooood :)

    • Jaime Olivo Jr

      Nice! You definitely restored my faith in buying big watches!

      • Style Girlfriend


    • Adam

      No offence to Timbs, but I invested in a pair of classic Red wings, they are definitely a fall/Winter go to. That and a tweed jacket. Fall is also the season to start retiring the lighterweight cotton and linen ties and to start busting out the textured Flannel and wool ones.

    • Jon

      For the office: 3/4″ length, black wool top-coat from Banana Republic, assorted brightly patterned scarves from J-Crew.

      For the weeked: Black or Brown “sherpa” hoodie from J-Crew and black knit stocking cap from J-Crew.

      All the time, brown chukka’s from Born.

    • Kevin

      I have way more than 3 but I’ll narrow it down to the few things I constantly wear. Levi’s trucker jacket, Olive field jacket, light wash denim western shirt, pocket t-shirts, caramel colored chinos, Levi’s 511s, navy blue shawl collar cardigan, OCBDs. blue suede Vans sk8-hi, brown 6″ timbs, gray woven Nike free run 2. Sorry for the run on.

    • Michael

      Since I’m in the Chicago area, fall can mean anything from 80s to well below freezing. My go to jacket is actually a combination of a nice waxed cotton jacket with a polartec zip up as a lining when needed. Chicago fall gets colder than English winter I think. Pants that will make some attempt to slow down a cold breeze. Shoes that can deal with slush or rain, which is most of my footwear except the desert boots or running shoes. For work I have some nicely shined wingtips that can shrug off reasonably crappy weather, and for days off I have some comfy and water proofed converse one stars.

    • Bobby

      Gray crew neck sweatshirt, dark jeans (my new pair of gustins), boots from lands end (crosby moc toe). Also, gotta run to the army-navy to get a new wool scarf.

      • Style Girlfriend

        I first read crosby moc too fast as “croc” – you had me scared for a minute!

        • Bobby

          Oh shoot i did mean to type croc – stupid auto-correct

    • Biscuit!

      I love boots – they just work. My issue is that I wear a 4E shoe! Anyone have any luck with extra-wide boots that can be dressed up?

    • Andrew
    • ThomasRankin

      I have a pair of brown ‘vintage’ (c. 2001) Doc boots that just live forever. My Scotch & Soda pea coat for extra crisp days. Still check the time on my phone like it’s outta style.

    • Ron

      Thanks Megan! I love the boots, just ordered a pair. Loving the rugged but stylish workwear boot!

      • Style Girlfriend

        awesome! can’t wait to see a pic when they arrive

    • java

      I haven’t checked in for awhile so imagine my surprise when I discover that the black form fitting leather bomber jacket I finally splurged on (weight, size, diet, fitness, and lifestyle in balance without yo-yoing in 3 years) is considered timeless and essential! I pair it with black chelsea boots and aviators. I’m in the South so we still get plenty of sun and days that fluctuate between 50 and 80 so the leather jacket is perfect.
      Another fall weather essential is the navy corded sport coat with brown patched elbows and patch pockets, Wolverine 1000 mile boots, and a Polo chambray shirt.

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    • NoNoBadDog

      I have a good pair of side zip brown leather boots. and a black lambskin leather jacket that I have been wearing for about a decade now. It is broken in comfortable and distressed unique to me. I will be very sad if something ever happens to this coat. I also have a green tweed wool flat cap from Ireland that keeps my shaved head warm. A hip flask with good bourbon is also essential I think, but hey thats me.

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