13 Smart Purchases That Have Helped Me Stop Overpacking

There once was a time when I couldn't even take a three-day trip without checking a bag. In fact, it wasn't that long ago. Even though I planned out all of my outfits (and still do), I didn't really rewear anything, and I packed far too many bags and shoes, which take up ample suitcase space. I've since reformed and am proud to say that I brought just a carry-on for a four-day trip to Mexico this spring.

How did I reform my tendency to overpack? For starters, I invested in a handful of pieces that are appropriate for many different types of trips, and I make a point to incorporate them into multiple outfits when I map out my packing list. These key items range from black cigarette pants to elevated sneakers to the sweater I even pack in the summer. Of course, I don't wear only these purchases when I travel. They've become staples in my day-to-day wardrobe as well, so they're worthy investments indeed.

If you're a member of the overpacker club like I was, keep scrolling to shop the specific items that helped to change me this year and find out why they're so useful.

Dôen Lula Pants

Dôen's high-waist cigarette pants are probably the most flattering pants I own. I'm not surprised in the least that they've sold out multiple times. I like to wear them out at night when traveling, but they're also great with flats and sneakers for a travel day or sightseeing day.

Reformation Clara Cashmere Cardigan

I'm pretty sure I own this cardigan in four colors at this point. It's the best cashmere crewneck cardigan on the market, in my opinion. It's lightweight but not thin, and the fit is cool and not frumpy in the least. It's a great layering piece for winter trips and is perfect for chilly evenings and planes in the summer.

Reformation

Clara Cashmere Crew Cardigan in Cherry

Reformation

Clara Cashmere Crew Cardigan in Cocoa

Reformation

Clara Cashmere Crew Cardigan in Parmesan

Leset Margo Tee

I don't remember the last trip I didn't pack at least one Leset Margo tee for. It's the perfect weight, it doesn't get too wrinkly, and it comes in all the best colors.

LESET

The Margo Tee in Natural & Midnight Stripe

Dear Frances Balla Mesh Flats

I'm done with packing bulky shoes, and it doesn't get more lightweight and space-saving than Dear Frances's airy Balla flats. I just wore them to NYC and walked a ton, and I was completely floored by how comfortable they were.

Dear Frances

Balla Slip-On Flats in Black

Dear Frances

Balla Flats in Red

Dear Frances

Balla Mesh Flats in Coffee

Posse Alice Mini Dress

There are a lot of linen dresses out there, but I'm convinced that the Posse Alice Mini Dress is the best of the bunch. It's fitted without being tight, the linen is incredibly soft, and it has pockets. I loved the black one so much that I ordered the white one soon after.

Posse

Alice Mini Dress in Black

Posse

Alice Linen Mini Dress in White

The Row 90's Bag

Finding a bag that works for travel is pretty tricky. I'd prefer to not pack more than one, and it needs to fit in my under-seat tote because I don't want it to have to count as my personal item. The one that checks all of the boxes for me is The Row's 90's Bag. It works for day and night, and it's petite but has plenty of room to hold all of my essentials. The leather is so high in quality that it doesn't show wear and tear easily.

The Row

90's Mini Leather Shoulder Bag in Borgogna Ans

The Row

90's Bag in Leather in Black

The Row

'90s Leather Tote Bag in Dark Aniline Ans

J.Crew Gwen Skirt

A Who What Wear team favorite, J.Crew's iconic Gwen skirt lives up to the hype. I've created so many different outfits out of it, and it looks just as chic with sneakers and flip-flops as it does with heels.

J.Crew

Gwen Knee-Length Slip Skirt in Viscose Charmeuse

J.Crew

Gwen Lace-Trim Slip Skirt in Textured Satin

SimonMiller Knotted Gala Mules

I always pack a pair of heels (usually of the kitten-heel variety), but I'm exceedingly picky about them. No bulky pumps or block heels are allowed in my carry-on. SimonMiller's Knotted Gala Mules were exactly what I needed. They're special yet versatile, and they always go with all of my warm-weather evening outfits.

Simonmiller

Knotted Gala Mules in Black

Simonmiller

Knotted Gala Mule Heels in Chocolate

Polo Ralph Lauren Brown Baseball Cap

I'm never without a baseball cap on a trip, and these days, it's usually a Polo Ralph Lauren one. Sure, the black, navy, and tan hats are great, but the chocolate-brown one is a game changer. Be prepared for everyone to ask where you got it.

Polo Ralph Lauren

The Iconic Chino Adjustable Baseball Cap in Nutmeg Brown

J.Crew Garçon Shirt

A button-down shirt (or two) is a must in my suitcase. I usually wear it at least once during the trip and then on the plane on the way home. J.Crew's Garçon Shirts are my current obsession. They're not too fitted and not too oversize, and they come in a plethora of colors and fabrics.

J.Crew

Garçon Classic Shirt in Cotton Poplin

J.Crew

Garçon Classic Shirt in Cotton Voile

Agolde Valen Jeans

I'm a big jeans person and never travel without at least one pair. Since discovering Agolde's Valen Jeans, one pair is all I need. They're the perfect timeless straight-leg fit, they're really comfortable, and the 28.25-inch inseam is the perfect length for my 5'4" height. I own four pairs now, so I think that sums up how I feel about them.

Agolde

Valen Jeans in Essence

AGOLDE

Valen Mid Rise Vintage Straight Jeans in Hitch

Dries Van Noten Sneakers

I usually skip over sporty, athletic sneakers for trips and instead opt for an elevated pair that's more appropriate for something like a fancy brunch. In an ideal world, I'd pack two pairs of sneakers, but if it's just one, I'm going with the dressier pair. Dries Van Noten's wildly popular retro sneakers are my favorite, and they've accompanied me on many planes over the past year or so.

Dries Van Noten

Leather and Suede Sneakers in Black

Dries Van Noten

Suede-Trimmed Leather Sneakers in White

Free People Lowen Midi Skirt

In addition to J.Crew's Gwen skirt, a skirt I love to travel with is Free People's Lowen skirt. It's an A-line midi skirt that comes in oodles of colors. (My current favorite is the red one.) I especially love it during the day with a tank and flats, sandals, or sneakers. It's the perfect easy summer outfit.

Free People

Lowen Midi Skirt in Cherry Tomato

Free People

Lowen Midi Skirt in Black