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Autumn in New York. My favorite cliche. Nostalgic and romantic, the icy tones of the glass and cement city overwhelmed by the greenery burning into oranges and reds. It’s the perfect playground for putting together a great outfit.

I’ve lived on the east coast for eight years, but somehow, I’ve never landed in New York in October, when the air is crisp but not too cold for a mini skirt, when the leaves are still clutching tree branches, when the wind isn’t barreling between buildings just a little too quickly. One of my best friends lives in the city, and we’ve been talking all year about making a fall trip to see her. Magically, our calendars all lined up for a gorgeous October weekend.

The weather’s going to be stunning, our itinerary is set—all that’s left is to choose my outfits. As a chronic over-packer, I find it useful to stick to a formula, especially for weekend trips. It leaves room for last minute swaps if I change my mind about an outfit, but keeps my suitcase organized and free from random pieces that don’t go with anything else I’ve packed.

The breakdown goes as follows: the nice dress, the night out, the cute jeans, the knit & tee, the casual dress & mini, and the boot & sneaker. You might be thinking, that’s just a list of basic pieces of clothing. And you’re right! But there’s more to it than just the pieces themselves—it’s about grabbing pieces that work with all of your other pieces. So let’s get into it.

The Nice Dress

This one’s pretty straightforward. The slightly nicer, dressed-up option for a cute, classy dinner or night out. This isn’t your going out outfit—you’re not thinking about what it would be like to walk into a sweaty bar wearing this. It’s your kind-of-fancy moment. The one I’ve chosen for this trip it’s an off-shoulder boucle maxi dress from Meshki. Comfy and warm enough, but still a fun moment.

I’m pairing the dress with a slim black knee high boot and a cow print purse. Since it’s a neutral toned look, I want to add some interest with the printed bag. I love a maxi dress as the focal point of an outfit, and considering the textured fabric and foldover neckline, I want to keep the rest of the look fairly simple to keep from overwhelming the look.

The Cute Jeans

Jeans plural, by the way. Two pairs. One plain, simple pair—I’m currently addicted to the AGOLDE Fusion Mid Rise jeans for a baggy low rise fit. And then one statement pair. For this trip, I’m going with the Lioness Carmela pants—a fun leopard printed denim. I find that a cool denim is one of the easiest ways to make an outfit look effortlessly cool, and for a short trip like this one, I’d rather pair the same simple tee or sweater with a different jean to refresh a look than pack a bunch of different tops. I find that a cool pant impacts an outfit more than swapping a fun top in but keeping the same pair of jeans.

The Knit & Tee

A comfy cozy neutral knit is essential. But what’s even more essential is that it works with both pairs of jeans, your casual dress, and your mini skirt. You never know if the weather’s going to switch up and demand more or less coverage, or if you’ll wake up not wanting denim anywhere near you. So pack a knit that can be swapped in with all of the other pieces you’ve packed. Because I am forever an overpacker, even with all of this, I’ll be packing one fun knit, too. A pop of color, just to have on hand in case of a fashion emergency.

The tee is your basic outfit building block for any layering necessities. Under your sweater, with your mini skirt, etc. Depending on what other pieces you’ve chosen, it’s a great piece to add dimension to simple outfits. The one I’m bringing is a light grey fitted baby tee that pairs with the white sweater I’m packing and the blue cardigan I’m bringing as my alternate. It’s the right length to be worn with both my pairs of jeans, and works with my mini skirt.

The Casual Dress & Mini Skirt

I am a mini girl. As in, mini skirts and mini dresses are everything to me. No matter the weather (I’m talking dead of winter) I will almost definitely have these in my suitcase. For this particular trip, I’m bringing this ultra soft drop waist black mini dress. It can be layered under both of my knits, and works with my boots or sneakers depending on the weather. For my mini skirt, I’ve chosen a simple medium wash denim one. Again, pairs well with everything in my suitcase, and is a piece I know I always feel confident in.

The Boot & Sneaker

Another irrefutable truth about me is that I am a heel girl. A tall boot with a mini is my bread and butter. But obviously, having a flat shoe on a trip is essential. I do like my shoes to be fun to some degree though, especially if they don’t have a heel. So for this trip I’m bringing the knee high heeled black boots I’ve mentioned, and a pair of red & pink Puma sneakers. They’re a fun color, but still pair with the rest of the pieces I’m bringing along.

The Night Out

So this is a unique case for the night out look, because this particular look is a Halloween costume. Since we’re traveling, it’s still important to plan a look that isn’t too cumbersome to fit easily into a suitcase. I’m going as Charli XCX, partly because it’s fun and partly because the outfit is easy, comfy, and can be rolled up into a small pocket of my luggage.

The effectiveness of this look really lies in the dramatic hair and smoky eye makeup, so the clothes are the easy part. Obviously not every weekend is Halloween, but the same rules tend to apply for a regular night out look: keep it simple, and lean heavily into the styling.

Sometimes, my favorite outfits are the simplest. Especially when I travel, I go for pieces that I know I love, and that I know I’ll always feel good in. Finding that perfect balance between comfort and style is key, especially on a trip like this one when I’ll be spending so much time outside and walking. Rarely are my trip outfits going to be my most iconic—this is not when I pull out my statement pieces or my coolest styles (except maybe for one of my nighttime looks). This is when I stay truest to myself and my core personal style. My staples are my best friends on trips like these, and the looks I’ve pulled for this trip are no different. Neutrals and comfy fabrics, and the occasional cool accessory and fun pattern—but mostly simple, straightforward, with a touch of femininity and softness. This is what works for me when it comes to preparing for trips, and as always, take what you love and leave what you don’t. If I’ve helped you make your suitcase just a little more organized (or avoid an I-hate-my-outfit crisis), then I’m thrilled you’ve found your way here.