#OOTD: The Best Way to Dress for a Casual Fall Day

Editor’s note: You’ve surely seen this hashtag lots of different places, including on Instagram. But how does that carry over to real life? The #OOTD series will take one great item and put together a versatile, stylish outfit around it. Look for past features here.

Now, we might be rolling through November, but with this up-and-down weather, it’s not quite felt truly, really … like fall. Has it? Well, maybe we’ll call this one an #OOTD for a casual … November (or December?) day. Either way, we’ll continue to push forward here on The Style Guide.  Situational dressing, although at first daunting, can  be one of the best parts of getting into menswear — a weekend coffee date? No problem. Heading out on a fall hike? We’ve got you covered there, too. But what about those in-between times? Maybe you’re dashing to the barber or strolling down the street to grab a beer — nothing too fancy, right? And yet, all you loyal Style Guide readers (I think there are a few?) know that even a casual, brisk fall day is a chance to mix and match your favorite style essentials. Some of the pieces below are investment-worthy, but they’re all built to last — and each is versatile in its own right. This is the type of garb to toss on for a perfect fall (or winter) Sunday, and you can even swap in a tough chambray shirt if you need to dress it up a little bit.  So, read on and stick around for more menswear shopping picks for the season.
Huckberry

Reach for comfortable, premium basics and durable boots on a casual fall day.
Reach for comfortable, premium basics and durable boots on a casual fall day.

The Jacket: Apolis Indigo Wool Chore Coat, $278 — Of the investment-worthy pieces mentioned above, the Apolis wool chore coat belongs squarely on that list. It’s perfect for layering, it’s sharp without being too dressy, and it’ll break in beautifully.

The Sweatshirt: Todd Snyder x Champion Pocket Sweatshirt, $98 — A certified modern-day #menswear classic, the Todd Snyder x Champion Pocket Sweatshirt is a cozy, comfortable and stylish second layer — trust me.

The Base Layer: Mack Weldon Pima Long-Sleeve Crewneck, $38 — The Mack Weldon team knows a thing or two about stylish, comfortable basics, and that’s why this pima crewneck is an ideal, warm base layer.
Beckett Simonon

The Pants: Flint & Tinder 365 Khaki Pant, $98 — The makers of your new favorite henley have done it again with a pair of 5-pocket pants that blend casual comfort and crisp style — every day of the year. As to your belt? Pick up a textured braided leather belt on the cheap from J. Crew Factory.

The Boots: Lanona Shoe Co. Academic Boot, $298 — The Academic Boot is another piece that, much like the Apolis indigo wool chore coat, ain’t cheap. But seeing as it’s a Huckberry  exclusive, made in Maine and built with Horween Natural Chromexcel leather? Ehh, the price is more bearable.

The Socks: Anonymous-ism Tribal Joint Crew Socks, $23 (Available via East Dane) Anonymous-ism is known globally for its subtly stylish, well-made socks — if J. Crew and East Dane carry them, you know they’ve gotta be good.

The Watch: Form-Function-Form Horween Leather Timex Chronograph, $119.98 — This casual outfit is filled with rugged style essentials, so why not reach for an affordably priced, durable Horween leather watch? Ehh?

The Hat: Carhartt WIP Key Ribbed Beanie, $35 (Available via East Dane)  — Sometimes, you don’t need to get too over-the-top with your fall and winter accessories — this navy cap is understated and high-quality.

Keep in mind that when dressing for a casual fall day, plenty of other pieces will work. Whether you layer up a rugged henley with a cotton chore coat or go with a slim chambray shirt and your favorite pair of dark denim, it’s important to keep versatile style and proper fit in mind — but hey, we all know that (wink, nudge). And in this instance, you can get a ton of mileage out of an indigo wool chore coat and classic khaki pants — that goes for casual weekend wear or versatile office style. Oh, and those Horween leather boots will break in beautifully over time while fitting in perfectly with this outfit’s rugged vibes (Editor’s note: If, however, you seek a more affordable pair of fall boots, this site has you covered in the meantime). Are there pieces on this list you would switch up? How do you dress for a casual fall day? Get style inspiration and join the #menswear discussion over on Twitter.
Buck Mason - Timeless Design. Made in America.

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