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Webb Weekly

280 Kane St.
South Williamsport, PA
17702


Fall Outfits 2026

Fall is here and, like any other middle-aged whimsical woman, I am basking in the outfitting possibilities of this season.

There are, of course, sartorial classics like flannel, plaid, trench coats, corduroys, big cardigans, and knee-high boots

But for this year’s autumn I’m looking to switch up my fall styling with some unexpected outfit formulas. If this is also of interest to you, then please read on for a few fall outfit ideas in the year of our Lord 2026.

First up, not-so-boring beige. So often beige can get a bad rap, but a monochromatic look is made much more interesting when you play with shape and silhouette. A funnel-neck jacket like Athleta’s Daymaker Jacket in the shades of either flax or stone boasts surprise features like adjustable cuffs, an adjustable bungee cord waist, and a stowable hood that allows for customized fits and proportions. Plus, the water-resistant material makes for a practical choice on a misty fall morning. Add a functional and fashionable jacket in a neutral with a midi skirt in a similar shade, like Everlane’s Seamed Midi Skirt in “trench coat khaki” with its semi-fluted hem for a bit of a flare to take beige from boring to brilliantly chic this season.

For a more casual look, don’t sleep on ringer tees with jeans for fall. Ringer tees are such a fun and simple way to incorporate a bit of character into your fall wardrobe. For a clean and simple take on this shirt, there’s Hanes Originals’ Short-Sleeve Ringer Tee in cotton featuring your standard white T-shirt with black collar and cuffs. These subtle details give a bit more interest to a pair of baggy jeans with sneakers. However, I can’t resist a graphic ringer tee with barrel-leg jeans and cowboy boots. Official Band Shirts has a Willie Nelson Unisex Ringer in navy and white stripes with a yellow collar and “On the Road Again” graphic that is very hard for me to resist putting in my virtual cart. To be fair, the amount of shopping I DON’T do for these articles should be commended.

Another denim take this season is pairing dark denim with olive or military green. This combo has several variants which are fun to experiment with. The readiest matchup is a camo tee like Carhartt’s Irvine Relaxed Camo T in army green with a dark-wash straight-leg jean. I’d play against type and finish this look with loafers, an oversized blazer, and a baseball cap. To push the color combo, consider a chambray shirt like the J.Crew Factory Chambray Tie-Neck Button-Up shirt in blue wash and pair it with chinos in olive green and still wear those loafers and a blazer from the T-shirt version of this outfit formula. A third option is pairing a denim skirt, like Lands End’s Soft Denim A-line Midi skirt, with a fatigue green jacket such as Eloquii’s Semi Stretch Two Button Blazer for a preppy-casual look. The best part of this outfit formula is that you probably already have pieces in your closet to create similar pairings.

Another color to try and work into fall looks is a pop of blue. Since vibrant blue isn’t a usual color associated with autumn, it can act as a stark contrast (in a good way) with your standard fall color palette. Zara’s Oversized Popline Shirt in electric blue is striking on its own, but when worn with a dark brown corduroy trouser like LL Bean’s Vintage Corduroy High-Rise Wide-Leg Pants in deepest brown or deep wine, each shade enhances the other for a boldly rich look. Or work blue in with accessories, such as Puma’s Easy Vintage Shoes in royal blue available from Zappos. A bright blue sneaker can embolden a standard tee and jeans outfit, or contrast with a more formal trouser and blouse ensemble. And even though the old “match your shoes to your purse” rule is no longer a hard line in the sartorial sand, when it comes to pops of fun color, you can certainly match up shoes and bags. For blue sneakers, consider finishing your look with a bag like Old Navy’s Large Preppy Bucket Bag in “ahoy navy”. I also love the idea of adding a blue bag and shoe to a playing-with-proportion monochromatic beige outfit.

Lastly, layers! There’s nothing new about layering for fall, but for this year, try some unexpected layers, or at least new-to-you layering techniques. For me, I’ve already started using sweater vests in lieu of a blazer or jacket for my office-set job. Specifically, a thrifted oversized menswear sweater vest. I also may experiment with layering pins and brooches on fall blazers to show a bit of quirky flair. Adding a kerchief or bandana can also be considered a layer. One outfit formula I’m hankering to try is a British khaki, pinstripe button-down, pullover sweater, bandana, and then a puffer vest with boots and a crossbody bag for a fall day of tchotchke shopping.

Hopefully some of these outfitting ideas will give you a bit of stylish inspiration as another Fall emerges.