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Tuesday Outfit: Preppy Swagger

Sep 8, 2026

I am so drawn to preppy fashion, even though I feel like I never quite pull it off. It requires a bit of swagger that I just lack. But this inspo photo, this photo has swagger by the truckload.

The vibes. Oh, the vibes. A hint of menswear, the relaxed feel of the pant with the buttoned up collar on the shirt. Incredible. Here’s how to rebuild it.

Pants. The pants are the key here. They need to be wide leg. Almost painfully wide. The pleat, in my view, is absolutely necessary because it plays with the drape and proportion of the outfit. And the fabric needs to be a little relaxed (this pant is linen, but it’s the wrong season to be shopping for linen).

The pants I chose are this relaxed knit pair from Haven Well Within. They feel like a sweatpants, but they drape so beautifully that you can’t tell. Another option are these wide leg pants from Everlane. Reiss has a more tailored option. If you’re really not about that pleated pant life, Ann Taylor has a slightly dramatic wide leg pant with a flat front. Plus-size? Torrid has a dark olive chino pant that will work.

Shirt. The fully buttoned up collar is what makes this look special. It lifts the simple button up into highly tailored status. Tucking the points of the collar into the crewneck sweater just takes it to another level.

My new favorite button up brand is Untuckit. Yes, they make women’s clothing too. Their wrinkle free Melanie shirt is machine washable and 97% cotton. It’s cut really beautifully in the collar and cuffs, so those things don’t lose their shape after one wash. I also like this shorter, slightly boxy Crosby shirt.

Sweater. A simple navy crewneck from J.Crew has never done anyone wrong. I have no notes. A friend has been cruising Poshmark and eBay for pre-2008 J.Crew cashmere. She pays somewhere between $200-$300 for a lightly used piece, but she swears it’s the new-old gold standard. Here is a guide to checking the tags.

Shoes and Accessories. Nothing says preppy like a horse bit loafer. The Gucci ones are a bit out of my comfort zone, so these Sam Edelman’s will have to do. J.Crew Factory also has a nice pair.

Also, a brown bag would have been easy here, but a navy one felt fresher. This one from Lo & Sons was the obvious pick. It’s the best laptop bag. A bit spendy at $350, but when you see the quality, you won’t question it.

For the jewelry, the inspo photo has white enamel statement earrings. I chose a pair of dramatic pearl earrings instead. I just wanted more pop. These ones from Brinker + Eliza just deserve their moment. I also added a dome ring from Monica Vinader. I thought the look needed a little something more. If you want a lot of something more, a hammered cuff is a good option.

For the styling, the slick backed bun is just it. I have bangs so this is not in my repertoire, but I dug up this 53-second tutorial, which absolutely nails it. To keep it smooth, I recommend this Briogeo stick that they gifted to me and I use on Sloane’s baby hairs. I would use it on myself, but like I said, BANGS. It works well, even after an hour on the playground dangling from the monkey bars.

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  1. Kate says:

    This is me all over.

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