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 will take one great item and put together a versatile, stylish outfit around it. Look for past features here.

The more you get into menswear and the art of dressing well, the more you realize how many situations it can help you through — that’s something I’m still learning everyday. That is to say, everything from your morning coffee run to what to wear to the gym are chances to extend and improve your personal sense of style (says the guy who wears old college tees to work out sometimes). The smallest situations and style details really do help set you apart, and that’s the approach we’re taking in today’s #OOTD. It’s a pretty specific situation — perhaps date isn’t the right word, but know that even when dashing out to grab coffee, it’s still a chance to look put-together. That goes for whether you’re meeting a friend, a date, your dog, your cat … you get the picture. And, it gives you an excuse to work more excellent #menswear into your rotation — that’s what we do at The Style Guide, folks. Plus, assuming it’s well and truly fall weather, it’s a nice chance to break out a few extra casual layers (or, you could just stick with that Taylor Stitch chambray shirt in the heat) and a great watch. There’s plenty more in store — read on below, and get more daily style inspiration via Instagram.

The Overshirt: Bridge and Burn Flint Overshirt, $182 — It’s a shirt! It’s a jacket! It’s a shirt-jacket, and with a neat cotton flannel lining and a rich indigo dye, it’s just the right weight to throw during a crisp Saturday or Sunday morning.

The Sweatshirt: Todd Snyder x Champion Pocket Sweatshirt (Available via East Dane), $98 — This sweatshirt is a stone-cold classic — add it into the essential menswear lexicon for the well-dressed guy. It’s clean, classic and again, a perfect layering weight for fall. Snag it here.

The Shirt: Taylor Stitch Everyday Chambray Shirt, $118 — Whether you go with white or classic blue, the Taylor Stitch Everyday Chambray Shirt is another absolute essential.

The Chinos: Levi’s Made & Crafted Slim Fit Chinos (Available via East Dane), $178 — These Levi’s Made & Crafted chinos are indeed pricey, but well-made, easily wearable for casual situations and a nice weekend upgrade from denim (although that works here, too).

The Sneakers: SeaVees Huckberry Chukka, $98 — Since you’re wearing a classic chambray shirt and chinos, it’s OK to go a bit more casual with these durable sneakers — the perfect weight, color and cut for fall.

The Socks: Anonymous-ism 5-Color Crew Mix Socks (Available via East Dane), $25 — Anonymous-ism socks are some of the best money can buy — your feet will thank you for this style splurge.

The Watch: KOMONO Walther Cognac, $179.95  — The Walther is the latest release from a new line being done by KOMONO — the brand’s Crafted Collection features a higher price point and premium materials, plus excellent design. Read a full KOMONO product review here.

The Belt: Anderson’s Stretch Woven Grey Belt, $116.98 — As with other Anderson’s belts, this one is going to cost you — but you get a belt that’s durable, comfortable and on-point stylistically (the texture fits right in with the colder climes of fall).

There are certain style moves that just work when it comes down to it — grabbing a stylish chambray shirt will serve you well, as will layering up with a Todd Snyder x Champion crewneck sweater. The slim-fit chinos and SeaVees sneakers blend sporty and tailored style, and premium finishing touches like those Anonymous-ism socks truly make a world of difference — and a heck of an impression, while we’re at it. The situation is surely different than dressing for a first date, but it’s no less important to look your best — even if you’re just relaxing over coffee with your dog, or your cat, or a book. Got questions, suggestions, additions or deletions? Drop me a line on Twitter.

Stay stylish,

-Beau