9 Chic and Timeless Outfits You Already Own
As we slowly say goodbye to summer and begin to welcome in fall, I’ve got “transitional” dressing on my mind. The shorts and bikinis simply aren’t doing it for me anymore, and instead I’m interested in the outfits I can start wearing now but will continue to get use out of in the coming months. Since I was already saving inspiration for my own personal use, today I figured why not share the screenshots I’ve been hoarding with all of you, too.
And not that I’m ever one to deter you from shopping, but let’s say one day you’re in a pinch (whether it’s for time, energy, or budget) and need to look chic and put-together in a flash. It’s important that you have an arsenal of outfits to fall back on. For that reason, I limited the below to those comprised of timeless basics most Who What Wear readers already own. After all, you are a well-dressed bunch of smart shoppers! Of course, if you are still working on your collection of wardrobe essentials or simply love to shop, I’ve included my favorite investment-worthy pieces one could buy to get the look too. Heard enough? Simply keep scrolling to get started.
While I love the blue, this monochromatic tee, skirt, and flats combo could be replicated with any color in your closet.
As a jeans-and-tee loyalist, I'm impressed by just how much a dark button-down elevates the look, and you can bet I'm taking note.
If, like me, you're dying to get back into your blazers, this tee-and-sandals styling is a smart way to get into your suits early. When the weather really starts to cool, you can simply switch in close-toed flats.
I loved this way of styling an all-white outfit with black accessories last year, and I'm still not over it.
Breathe new life into any old midi or maxi skirt by pairing it with a boat-neck top, belt, and Mary Jane flats.
Say it with me: white top, black trousers, kitten-heeled sandals.
A fun belt and ballet flats are all you need to take your white button-down and jeans to the next level.
For sneaker days, just add trousers and a tucked-in sweater for a can't-go-wrong look.
This is a reminder to myself to stop tucking in my tops and wear them out instead.
Since starting as an intern back in 2013, Nicole Akhtarzad Eshaghpour has held several roles here at Who What Wear, and she is currently Editor-at-Large. Upon joining, she was a senior about to graduate from business school at USC. Fast-forward to 2025, and she's moved to NYC from her hometown of Beverly Hills and spends her workdays a little differently from when she was just starting out. Currently, she focuses on a weekly mélange of shopping content and her Trust Me—Buy This newsletter. As far as her personal style goes, she's largely drawn to neutral, classic pieces but will always make an exception for something colorful or bejeweled as long as it's deemed worthy enough. After all, the only thing she loves more than a party is dressing up for one. On her downtime, she can usually be found at home eating something delicious and trying to force her husband to watch Summer House.
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