What to Buy for Fall If You Don't Want to Regret It Next Year (or the Year After)

If your shopping goal for the coming season is to spend smartly and buy things you won't want to discard after a few months, then you're in the right place. As a notoriously safe-playing and risk-averse shopper, I’ve come to know what items are worth spending on and what will feel dated, or worse, not hold up well in the near future. Luckily, when it comes to fall fashion, luxe basics are the cornerstones of a chic and cool wardrobe anyway, so it’s easy to spend wisely while still buying pieces you really love and are excited to wear. Below, I’m highlighting seven such categories. From outerwear essentials to knits, boots, bags, and more, these are the pieces you’ll not only love this cold-weather season but can enjoy for years and years to come. Simply keep scrolling to get shopping, and take in some outfit inspo for each piece along the way.

Simple sweaters

I cannot think of a category where the phrase "buy cheap, buy twice" is more applicable than knitwear. I've learned the hard way that not all sweaters are created equal, and it's better to invest in a just a couple at higher price points than many cheaper ones that won't make it past the current season. Of course, be sure to care for them properly too.

Classic outerwear

Coats and jackets are my biggest shopping vice, and I like to think it's excusable to hoard them because, if you buy classic ones, they truly never go out of style. At most, you'll put them on the back burner for a year or two, but I've learned that they always come back.

Everyday boots

Statement-making boots and heeled options are nice and all, but if you want bang for your buck, splurge on a pair you'll use the most frequently. For me, that's the everyday boot. It can be any material, any style, even have a low heel, but it has to be something comfortable, neutral, and easy to pair with everything.

Polished pants

Perhaps it's because I'm in my trouser era, but I truly think that good pants are not only the cornerstone of a polished outfit, but they can be the basis of your whole look. Find a good pair of pants, and getting dressed feels almost too easy. No matter what you style with them, you'll always look put-together in trousers.

Luxe totes

Whether or not they're "trending," sometimes you just need a big bag to carry around all your stuff, and when you do, it's nice to have an option you love. A bag can make or break an outfit, and the below are sure to make it every time.

Layering tops

Fall weather can be quite variable, which often means that dressing in layers is not only recommended but necessary. Versatile, layerable tops will make that an easy feat. Plus, you can likely use them in other seasons, too.

Sleek flats

For the days and outfits where boots just don't look right and sneakers won't do, a sleep pair of flats will be your saving grace. Luckily, this season, the options are endless. Whether you're partial to a classic ballet, loafer, mule, or all three, there's no shortage of pairs you'll love and want to wear on repeat.