There’s a certain magic in early fall down South. The mornings have that first whisper of cool air, but by lunch you’re back in short sleeves. Football is in full swing, dove fields are alive, and weekends stretch between tailgates, porch drinks, the golf course, and the occasional road trip. Dressing for this season isn’t about diving headlong into heavy flannels and boots just yet — it’s about balance. The kind of style that keeps you comfortable from the cool start of the day until the last bourbon at night.
Layering light is the key. Early fall is where those cotton quarter-zips and lightweight sweaters earn their keep. Pair one with a crisp oxford or a short-sleeve polo underneath, and you’re ready for a morning coffee run or a noon kickoff. Chinos are a staple year-round, and a good pair of comfortable (read: not too tight) jeans has a place in the rotation. If the sun lingers, cuff them at the ankle and let your loafers or sneakers breathe a bit.
Footwear transitions with the season too. Early fall calls for chukka boots, loafers, and lightweight sneakers. Boots for those long days and I like clogs around the house. A good suede chukka might be the most versatile shoe in your closet: refined enough for dinner in town, rugged enough for a Saturday tailgate. The trick is leaning into pieces that bridge both worlds.
At the heart of it, early fall style is about transition, not transformation. You’re still rooted in the ease of summer: breathable fabrics, simple color palettes, but layering in just enough weight to acknowledge what’s coming. It’s Southern style at its best: practical, comfortable, and sharp without trying too hard.
So lean into it:
From top left:
1. Eton Contemporary Solid Dress Shirt: It’s a great season to add a really nice dress shirt (on sale!). Remember – it’s wedding season, too.
2. Kamakura OCBD Shirt – U-Stripe: University stripe OCBDs might be the most underrated button-ups in the closet. They go with everything and look smart. Mrs. RCS steals mine all the time.
3. Duck Head Henson Merino Crewneck Sweater: Layer, layer, layer.
4. B.Draddy Bradshaw Shirt-Jacket: Very lodge-wear. Looks cool dressed down to keep you warm in the morning, or dressed up with jeans and chukkas on a date.
5. Holderness & Bourne Burton Long Sleeve Polo: The hero of the Fall. The Burton from H&B wears like a dress shirt, but feels like a t-shirt. The fabric is amazing, and the cut is just right. You’ll be able to toss the pigskin without missing a beat.
6. Pennbilt Plainsman Chinos: My go-tos this time of year.
7. Smartwool Socks: I love these. They work with my Blundstones, my New Balance, under waders, and with my clogs (#11).
8. Manyatta Belt: Add some waist flare. So many to choose from…
9. Boardroom Socks Merino Herringbone Socks: Clean out that sock drawer, and add some that’ll actually get some wear.
10. Loake Pimlico Suede Chukka Boots: The utility boots of the Fall.
11. Res Ipsa Kilim Clogs: My version of a utility slipper.
12. Levi’s Stonewashed 501 Jeans: While breaking in your own pair is fun, cheating a little to get just the right wash ain’t too bad. These “dark stonewash” jeans look good.
What did I miss?
This is all great stuff. Love the look here. My adds would be 1) a rugby shirt, because let’s bring back large horizontal stripes (you had a good one on insta recently, but I forgot the brand), 2) corduroy trousers, and 3) a chore coat that a working man would actually buy (not $450). Also, I’m still on the hunt for the right argyle sweater, with muted, autumn colors.
specifically, the cord trousers should be wide wale and pleated. Maybe a little baggy. No skinny, no stretch. Old school. Should somehow have a faint small of pipe tobacco. The thin wale, 5 pocket cords are different and not the style I’m talking about here.
Check out Morris & King (Charleston) and J. Press- right up your alley and both check all the boxes.
Withernot and J. Crew have great rugbys. Also, Brooks Brothers wide wale corduroys are cut well without being too slim or too baggy.
For rugby shirts I personally like the ones from Barbarian Sportswear. They specialize in rugby gear and the shirt I have from them seems pretty well made.