20 Wardrobe Staples You Can Wear On Repeat From Now Through Fall

Don’t get us wrong, we’re enjoying summer as much as everyone else, but we’re already looking ahead to the fall, particularly all the chic and cozy fall outfits we’ll be wearing. But what about that (somewhat dreaded) in-between phase? When it’s not too hot and not too cold and not quite sweater weather yet? If you stress over putting together outfits, particularly in that late August through early October phase, then it’s time to refresh your wardrobe with basics for easy-to-throw-together transitional weather outfits. 

If you’re wondering which pieces you can wear from the summer through the fall, we have some proposals for wardrobe staples that can be worn across seasons and styled differently depending on the weather and occasion. From basic T-shirts and denim jackets to midi skirts and ballet flats, we’ve compiled a mix of tops, bottoms, dresses, outerwear, and shoes suitable for summer to fall outfits. For instance, on cooler summer days, opt for light knits and relaxed jackets, and on warmer fall days, layer multiple pieces together. Scroll on to see which clothing items and shoes you can add to your closet right now to help easily build transitional weather outfits.


Transitional Tops

When the weather is cool, you can be lenient with your shirt choices, especially when its chillier because you can just layer up. For a tried-and-true option, you can’t go wrong with a crisp white button-down shirt, no matter the season. Go for one that’s slightly oversized so you can wear it open or closed and with the arms rolled up for a relaxed (and non-sweaty) fit. Classic T-shirts, like the one below, are another go-to. Stick to a clean white color or an off-white creamier color for true fall vibes. Other trends to partake in for the remainder of summer and beyond include layering sheer pieces and donning off-the-shoulder tops, slightly elevating your basics with interesting details.


Transitional Pants & Skirts

For bottoms, you may want to stick to longer hemlines when cooler weather hits, moving away from denim shorts and mini skirts and towards wide-leg jeans and midi and maxi skirts. As we know, denim can be worn effortlessly across all four seasons, but styles like wide-leg jeans and maxi denim skirts are trending — and are particularly great for transitional dressing since they leave some breathing room for your legs. Midi skirts are also just as versatile. Wear them with sandals and sneakers in the summer or heels and boots in the winter (and add a pair of tights underneath if necessary). Or go for a pair of lounge-y tapered pants, like the ones part of the Free People knit sweater set above.


Transitional Dresses & One-Pieces

Another simple way to create a transitional weather outfit is by sticking to a dress or another one-piece, like a jumpsuit or pair of overalls. While you likely have a closet full of summer dresses right now, it’s not too early to start looking for fall dresses. What does this look like exactly? Well, we recommend going for lightweight ribbed dresses, sleeveless so they can be layered with a cardigan or jacket, or short-sleeved with interesting details. They can be super casual or more elevated (think: buttons, belts, collars, and slits). But are you more of a pants person than a dress person? Then consider finding a versatile jumpsuit that can be dressed up or down with your shoes and accessories or a durable pair of overalls that can be paired with a classic T-shirt (see above!)


Transitional Outerwear

It’s layering time. An easy way to cover up without wearing an ultra-cozy and warm long-sleeve top is to throw lightweight outerwear overtop your shirt or dress. A cardigan sweater is so quintessentially “fall,” but you can make it work in the summer too, especially if the fabric isn’t too thick or heavy and if the style has a low neckline or buttons for a non-constricting fit. Other staples that you likely already have in your wardrobe and that you can wear time and time again include denim jackets (like the one below with a vented back), shackets (the brilliant shirt-jacket hybrid), and other relaxed fit jackets (like the wind- and water-repellent one from Lululemon).


Transitional Shoes

As the days and nights get less steamy, you’ll start stepping out of your sandals and flip-flops and into more closed-toe shoes. For an everyday shoe, go for a pair of chic, seasonal-less white sneakers or a pair of open-back flat mules. If you’re looking for a slightly more elevated shoe that you can wear to work (and gives more preppy fall vibes), consider classic loafers. And whether or not you love ballet flats, their resurged trendiness means you’ll continue seeing them throughout the summer and well into the fall. They’re sleek, versatile, and easy to throw on for a put-together outfit.


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