9 Fall Wardrobe Investments I Regret Not Making in My 20s

Wardrobe investment advice



So I figured I'd give this story a go before I forget what I even wore in my 20s. (Given that I spent several minutes the other day trying to remember if I'm 35 or 36 (it's 36), it's certainly possible.) But just as important as remembering what I did wear is what I didn't wear. For much of my 20s, I spent my clothing budget on trendy, inexpensive items that I'd quickly tire of. There are certainly exceptions but for the most part, I wasn't particularly worried about longevity when I'd decide what to buy. I've spent the first half of my 30s making smarter wardrobe investments that I wish I'd started making earlier on. 

Since fall is on the horizon, I've been thinking lately about the types of pieces I wear the most this season, year after year, and they're not the same trendy accessories, going-out tops, and dresses (to name a few) I was wearing 10 years ago. This is partly because my style has changed since my 20s and partly because I wasn't making that many lasting purchases. My budget was certainly more limited then, as is the case with many 20-somethings, but I regret not living by the 'ole less is more/quality over quantity adage a little more. 

With that, keep scrolling to shop the nine wardrobe investments I wish I'd made in my 20s, that work for every age group.

Non-Trendy Jeans

I'm someone who's always on the hunt for the next denim trend, which is all well and good, but the jeans I wear the most are those that can't be classified as a trend. They have a straight leg, a high waist, and a medium wash, and no other defining qualities, and that's what I love about them.

High-Quality Outerwear

Coats can be pricey, so I tend to wear the same ones for several years in a row at least, which is why I think outerwear is a very worthy investment. You can really tell the difference between a cheap and a high-quality wool coat, for example, so this is an area that's worth more of a splurge.

Fine Jewelry

While this is certainly more of a year-round investment than a specific fall one, when summer ends, I always want to put on more nice jewelry. And unlike when I was in my 20s, there are so many good DTC fine jewelry brands on the market now, so high-quality pieces are more affordable than ever. I can say with confidence that I wear very few of the costume jewelry pieces I bought in my 20s, if any.

Oversized Button-Downs

While I wore button-down shirts differently in my 20s (i.e. not with bike shorts), I wear them now as much as I do then, so it would've been worthwhile to invest in some nice ones in classic colors and prints, especially since they're not that big of an investment. You live, you learn.

Classic Black Blazer

Seems like a no-brainer, but I too often avoided investing in "boring" items in my 20s. Sure, a black blazer may not be the world's most exciting thing, but think of all the non-boring things you can wear with it! My advice is, save up for a nice one made with quality material that will help it to drape nicely and last.

Tote Bag

When I got my first office job in my 20s, I quickly realized that I was going to need a big bag to transport everything I'd need in an 8-hour+ day. I recall going through a lot of tote bags that would eventually get beat up and be forced into retirement. If only I'd put that money that I used on many tote bags to one really nice one...

Cashmere Sweaters

There's nothing worse than a thick, itchy sweater, am I right? I've suffered through my fair share of those, and I'm not sure why when you can get cashmere sweaters for a good price, and they're just as warm as their thick, itchy counterparts.

A Nice Belt

Belts are one of those accessories that I just forget to buy, but if I had more nice, neutral ones, I'd wear them more and my outfits would be better for it. A high-quality leather belt can last for years and be worn almost every day, if you so please. When you think about it that way, the cost per wear makes even a designer one seem like a steal.

Cold Weather Accessories

Warm accessories are not only essential—they can really make an outfit look expensive. Just think of what the below scarf and leather gloves would do for a sweatshirt and jeans. I used to stock up on cold-weather accessories for cheap at Zara, and while they were cute, I regret not investing in some nicer ones that I'd still use at age 36.