Let’s talk NYC outfits- because getting dressed in The Big Apple is an experience all by itself. Between the street style, the endless walking, and somehow ending up in three different neighborhoods before lunch, I knew I needed outfits that could keep up.
But instead of buying a whole new wardrobe for the trip, I challenged myself to create my looks using what I already owned. I mixed wardrobe basics with thrifted finds, played with prints, added a few styling hacks, and let my accessories do some of the heavy lifting.
The result?
Outfits that felt fresh, personal, and completely me without requiring a suitcase full of new clothes. So let’s get into what I wore in NYC and how the three-step styling formula helped me turn the pieces already in my closet into looks I couldn’t wait to wear.
I created six NYC outfits using the same styling strategies I teach here on this very blog. And I don’t just want to show you the finished looks- I want to bring you into my thought process and show you exactly how I put them together. I’ll break down the wardrobe basics, thrifted pieces, print mixing, styling hacks, and little personal touches that helped turn each outfit into something that felt like me.
Think of this as a peek inside my styling process: this is me practicing what I preach, not just talking about it. So as you look through each outfit, I hope you’ll start thinking about your own closet and all the different ways you can make what you already own work a little harder for you.
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1. Airport + Hitting The Ground Walking (day 1)
I arrived in New York early in the morning and knew I was going to hit the ground running—or, more accurately, walking. So I wanted an outfit that felt airport chic enough for the journey but could still carry me through a full day of exploring the city.
Cami || Trousers || Rugby (similar) || Sneakers || Bag || Sunglasses (similar)
I started with a new pair of khaki barrel-leg trousers and paired them with a navy-and-white striped cami. If you remember my 7 Lazy Summer Looks, you might recognize the cami; I loved it enough to grab another one in a different color. For shoes, comfort was non-negotiable, so I went with my New Balance 2002R Dad Sneakers from the Rain Cloud collection. To bring in a little color and give the look that effortless preppy feel, I grabbed my blue-and-green striped rugby polo and tied it around my neck.
For accessories, I kept things simple but intentional: my Louis Vuitton Speedy 30 with charms, khaki sunglasses, and my everyday gold jewelry.
How I Styled It
This outfit took us right back to the wardrobe essentials. The khaki trousers gave me a classic foundation, while my dad sneakers, everyday handbag, and rugby polo were pieces I already knew could work with countless outfits.
Then I applied the three-step formula.
Step 1: Start With a Piece That Speaks to You.
My starter piece was the striped cami. It wasn’t necessarily the loudest piece in the outfit, but the stripes gave me something to build around and immediately created a direction for the look.
Step 2: Build Around Your Closet Staples.
The khaki trousers became my foundation. They’re exactly the kind of wardrobe staple I want in my closet because they can move between casual, polished, and everything in between.
Step 3: Add Your Personal Style Twist.
This is where the outfit really became mine. Instead of simply wearing the rugby polo, I tied it around my neck for a pop of color and a preppy touch. Add the charms on my Speedy, the khaki sunglasses, and my everyday gold jewelry, and suddenly the outfit feels styled without feeling like I tried too hard.
And that’s really the goal: using a few intentional details to make simple pieces feel like a complete look.
Shop the Look
You don’t need these exact pieces to recreate the outfit. Think of this as a formula you can recreate with what you already have:
- Khaki trousers
- Striped or solid cami tank
- Rugby polo shirt
- Dad sneakers
- An all around handbag (think wardrobe essentials list)
- Simple gold jewelry
- Sunglasses
2. Block Party in Harlem (Later That Night)
Later that night, I headed to a block party in Harlem, so the assignment was simple: summertime fine, cute, and comfortable enough to actually enjoy myself. This look is also a good reminder that building a sustainable wardrobe doesn’t mean every single piece has to be something you’ve owned forever. Almost everything in this outfit was new to my wardrobe, but I still used pieces I already loved to pull the whole look together.
I started with a black-and-white polka dot halter top and matching mini skirt-skort set from Urban Outfitters. Then I layered it with a white windbreaker covered in smaller black polka dots that I found on TikTok Shop for less than $30. And here’s a little styling trick I swear by: when you’re mixing polka dots, don’t overthink it. You can play with different colors and different dot sizes and it can still work beautifully together. Here, the larger black dots on the two-piece set gave me a bold base, while the smaller dots on the jacket created just enough contrast to make the print mixing feel intentional.
Top (similar) || Skort (similar) || Jacket || Sneakers || Budget Friendly Option || Sunnies (similar) || Bag
For shoes, I pulled out my now-beloved Jacquemus x Nike Moon Shoes. They’re lightweight, low-profile, and perfect for summer when you want a sneaker that doesn’t overwhelm the outfit.
And you already know I wasn’t leaving out without a pop of color. I brought in an old pair of clear pink Gucci oversized round sunglasses and paired them with my mini pink Telfar bag. The pink accessories gave the black-and-white outfit just enough color without competing with the prints.
How I Styled It
This outfit is a little different from the first look because I didn’t necessarily follow the three steps in order—and that’s okay. The formula is a framework, not a rulebook.
I started with Step 1: Start With a Piece That Speaks to You, but instead of building from one single statement piece, I let the polka dot two-piece set establish the direction of the entire look.
Then I jumped over to Step 3: Add Your Personal Style Twist.
The low-profile sneakers kept the look casual and comfortable, while the clear pink sunglasses and matching mini bag brought in that pop of color that made the outfit feel like me. The mixed polka dots added another layer of personality without needing a ton of accessories.
This is also a great example of why I don’t believe personal style should feel like following a checklist. Use the formula as a starting point, then play. Sometimes your statement piece is obvious. Maybe it’s the print combination. Sometimes it’s the accessories that completely change the energy of the outfit.
Shop the Look
You don’t need these exact pieces to recreate the vibe. Look for:
- Black-and-white polka dot two-piece set
- Polka dot jacket or lightweight windbreaker
- Low-profile sneakers
- Oversized sunglasses
- Mini shoulder or crossbody bag
- A colorful accessory for your personal style twist
3. Matcha, Brooklyn Bridge & The Staten Island Ferry (day 2)
Day two started with a little dilly-dallying—which, in New York, still somehow turned into a full day of matcha runs, park-bench lounging, walking across the Brooklyn Bridge, and catching the Staten Island Ferry. 😂 With that much ground to cover, I needed an outfit that could handle the mileage while still giving effortless tomboy, but make it cute.
I started with a simple white ribbed tank from SHEIN that I’ve had since last spring. Then came one of my favorite styling hacks: I took two thrifted men’s button-down shirts– one blue-and-white striped and one plaid- and combined them to create an asymmetrical skirt. Yep, a skirt made from two men’s shirts. This is exactly why I love styling with pieces that aren’t necessarily intended to be worn the way you wear them. Sometimes you just have to look at your closet a little differently.
Tank Top (similar) || Jacket (similar) || Sneakers || Socks || Button down 1 (similar) || Button Down 2 (similar)
Then I pulled out an older cropped Zara denim jacket and gave it another styling hack. Instead of actually tying it around my waist, I buttoned the top button and the button at the waist and let the rest hang. It creates the illusion of a jacket tied around your waist without all the extra bulk—and, in my opinion, looks way cooler.
I finished the look with the same Dad Sneakers from Day 1 because, let’s be honest, New York requires a LOT of walking. I added my burgundy Miu Miu Beau-style bag from my $100 gift-card shopping spree earlier this year and finished with gray sunglasses with a subtle maroon tint.
The result was exactly what I wanted: comfortable, functional, a little tomboy, a little playful, and completely effortless.
How I Styled It
This look is where styling creativity really took over.
I started with Step 2: Build Around Your Closet Staples by using a basic white ribbed tank and the same Dad Sneakers I wore on Day 1. These are the kinds of pieces that earn their place in my wardrobe because they can support so many different looks.
Then I used styling hacks to create my statement pieces. Instead of purchasing a skirt, I transformed two thrifted men’s shirts into one. Instead of wearing my denim jacket traditionally- or actually tying it around my waist; I used it to create a completely different silhouette.
And that is one of the biggest reasons I love having a sustainable wardrobe: the more creative you become with what you own, the less you feel like you need to constantly buy something new.
This outfit also proves that comfort doesn’t have to mean sacrificing style. When I know I’m going to be walking miles, I start with the practical pieces and then build the personality around them.
Shop the Look
For this look, think about what you already have before you shop:
- White ribbed tank
- Two oversized men’s button-down shirts
- Cropped denim jacket
- Dad sneakers or another comfortable low-profile sneaker
- Burgundy or deep-toned everyday bag
- Tinted sunglasses
The takeaway: Before you decide you need something new, ask yourself, “Can I wear something I already own in a completely different way?” A little creativity can turn a basic piece- or even two completely unrelated pieces; into something entirely new.
4. Dinner & Broadway (night 2)
Okay, girlie pop; this one might be my favorite look of my NYC outfits. Later that night, I was headed to dinner and a Broadway show, so naturally the outfit needed to be a little more extra. We had dinner at the super cute, Sex and the City-style restaurant Obvio, where we even got to sit on the stage while THEE Tracee Ellis Ross graced the stage with her All the Brilliant Things performance. Needless to say, I was GAGGED. 😂
For the outfit, I started with a summer version of a classic: a blue-and-white striped button-down. I recently picked up this sleeveless version from Aloft, and I love the little twist; it ties at the back of the waist, giving me that classic blue-and-white stripe we know and love while still feeling light and summery.
Top || Pants || Brooch (flower similar) || Heels (similar) || Bag
Then I brought in the statement piece: a pair of navy blue origami-style paper-bag trousers. The shape alone did a LOT, so I let the trousers have their moment and kept my foundation relatively simple.
For shoes, I went right back to my wardrobe essentials with my cow-print slingback heels. Yes, cow print. Don’t forget we can take any stripe and mix it with an animal print. And because apparently I wasn’t doing enough already, I added a mini red vanity-style top-handle bag I found at SHEIN. Don’t forget we can take any stripe and mix it with an animal print.
Then we went all the way into…
Step 3: Add Your Personal Style Twist.
This is where I had fun. The red tie with tiny navy polka dots introduced another print while connecting back to the colors already happening in the outfit. The brooches, pearls, and red bag added layers of texture, color, and personality.
And here’s the thing: sometimes personal style means knowing when to stop, and sometimes it means saying, “You know what? I’m gonna add one more thing.”
This outfit worked because there was still a thread connecting everything; the navy, white, and red color story kept all of those seemingly random details from feeling random. The prints weren’t identical, the accessories weren’t matching in a traditional sense, and the pieces weren’t all from the same style category. But they all had a reason for being there.
That’s the art of mixing.
Shop the Look
You can recreate the energy of this look without copying it piece for piece:
- Sleeveless striped button-down
- Statement trousers
- Printed slingback heels
- Mini top-handle or vanity-style bag
- Men’s tie
- Oversized brooch
- Pearl necklaces
- A second statement accessory
The takeaway: Don’t be afraid to layer your personality into an outfit. Start with a strong statement piece, ground it with wardrobe staples, and then let yourself have a little fun. Sometimes the most memorable outfits happen when you stop asking, “Does this match?” and start asking, “Does this feel like me?”
5. Brunch in Harlem & The Museum (day 3)
By Day 3, I was fully in my “chill, but still stylish” era. I had brunch in Harlem and a museum on the agenda, so I wanted something comfortable enough for another day of walking but still very much giving I put this outfit together on purpose.
I started with a very old Kendrick Lamar concert tee I’ve had in my wardrobe for years. Instead of wearing the logo on the front like I normally would, I turned the shirt around so the back graphics became the focal point, then knotted it at the back to create a cropped, fitted T-shirt situation. Same T-shirt, completely different look.
Pants || Sneakers || Budget Friendly Option|| Hat || Bag || Sunnies
For bottoms, I paired it with brown-and-white gingham wide-leg cropped pants. The gingham brought in another print without competing with the graphic tee, and I went back to my Jacquemus x Nike Moon Shoes for a lightweight, comfortable sneaker that could handle another day of NYC mileage.
Then I added one new piece specifically for the trip: a tapestry New York baseball cap. It was the perfect little souvenir and styling piece, giving the outfit a very literal nod to where I was without feeling like I was wearing a tourist costume.
I finished everything with the same gold aviators I’ve been wearing all spring and summer and my Off-White YSL quilted bag.
How I Styled It
This look is a prime example of reworking what you already have and using one or two new pieces to give the outfit a fresh personality.
For Step 1: Start With a Piece That Speaks to You, I started with my Kendrick Lamar concert tee. But instead of wearing it the obvious way, I changed the orientation and silhouette. Turning the graphic to the front and knotting the shirt in the back completely changed the way the T-shirt looked and gave an old favorite a new life.
Then came Step 2: Build Around Your Closet Staples. The gingham pants, my Moon Shoes, gold aviators, and quilted bag were all pieces that could easily work beyond this particular outfit. They’re the foundation that makes the look practical enough for a full day in the city.
And for Step 3: Add Your Personal Style Twist, I brought in the NYC tapestry cap. It was a new addition to my wardrobe, but it didn’t require me to build an entirely new outfit around it. It simply added a little personality—and a little New York; to pieces I already owned.
This is exactly how I want you to think about adding new things to your wardrobe. You don’t have to start over every time you want your clothes to feel new. Sometimes one fresh piece is all you need when you already have a solid foundation to work from.
Shop the Look
Start with what you have, then look for pieces that give you the same feeling:
- Oversized or vintage-style graphic T-shirt
- Wide-leg cropped pants
- Printed or graphic baseball cap
- Low-profile sneakers
- Gold aviator sunglasses
- Quilted everyday bag
The takeaway: Before you retire an old favorite, try styling it differently. Turn it around, knot it, layer it, tuck it crop it, or pair it with something unexpected. A new perspective can make an old piece feel brand new.
6. Omakase & Vinyl Listening (day 3)
Later that evening, I headed to a bomb omakase dinner paired with a vinyl listening session, so naturally I wanted the outfit to feel a little elevated while still staying true to my style. And this look is probably the best proof that repeating pieces does not mean repeating outfits. In fact, one of my favorite parts of putting together these NYC outfits was seeing how many times I could pull from my existing wardrobe and make the pieces feel completely different.
Top || Pants (similar) || Heels (similar) || Hat || Bag
For my statement piece, I started with what looks like another simple sleeveless white button-down. But think again. 😂 Turn around and you’ll find a full halter top. I picked this one up from the KBB by Kalana drop at Target, and I love how something that looks so classic from the front has a completely different story from the back.
For the bottoms, I brought back the same balloon pants I showed you how to style several articles ago. Yep! the same ones. And because I clearly wasn’t finished with her, I brought back the tapestry NYC baseball cap from earlier in the trip too.
Then came the color. I added a pair of mustard velvet heels with a rhinestone brooch on the heel, which gave the neutral base just the right amount of richness and sparkle. I finished the look with leafy gold drop earrings and a mini Gucci bag.
How I Styled It
This look is a perfect example of Step 1: Start With a Piece That Speaks to You, while also showing you that a wardrobe essential doesn’t have to be basic or boring.
The white halter/button-down hybrid was my statement piece. From the front, it gives you the familiarity of a classic white shirt, but the open back completely changes the silhouette and makes it feel special.
For Step 2: Build Around Your Closet Staples, I went back to those balloon pants you’ve already seen on the blog. Rather than saving them for one specific outfit, I treated them like the versatile wardrobe piece they are and gave them a completely different supporting cast.
And then, of course, Step 3: Add Your Personal Style Twist.
The mustard velvet heels brought in color, texture, and a little drama. The rhinestone detail on the heel added another unexpected element, while the gold earrings and mini Gucci bag polished everything off. I even brought back the NYC cap, proving that you can repeat an accessory during the same trip and still make it feel fresh when the rest of the outfit changes.
And THAT is the whole point.
When you have a wardrobe you know how to work with, you don’t need a different piece for every occasion. You need different ways to style the pieces you already love.
Looking back at all of these NYC outfits, I repeated sneakers, accessories, wardrobe staples, and even entire bottoms—but the outfits never felt the same. That’s the beauty of developing your personal style. You’re not constantly starting from scratch; you’re building on what you already have.
Shop the Look
To recreate the feel of this look, look for:
- Sleeveless white button-down or halter top
- Balloon or wide-leg trousers
- Statement velvet heels
- Embellished or brooch-detail shoes
- Gold statement earrings
- Mini handbag
- Baseball cap
The takeaway: Don’t underestimate the power of repetition. The goal isn’t to own more clothes—it’s to discover more ways to wear the clothes you already own. And if these NYC outfits taught me anything, it’s that a good wardrobe can travel a whole lot further when you know how to style it.
In Conclusion: Style What You Already Own
And there you have it; six NYC outfits, one very well-walked wardrobe, and a whole lot of proof that getting dressed doesn’t have to mean constantly buying something new.
What I loved most about getting dressed for this trip was seeing how many ways I could rework pieces I already owned, mix in a few newer finds, play with prints and styling hacks, and still make every look feel completely different. That’s really what building a sustainable wardrobe means to me: not limiting yourself, but creating more possibilities with what you already have.
If these NYC outfits gave you a little inspiration to shop your own closet differently, I’ve got even more for you. You can watch the full NYC vlog on my YouTube channel to see the trip, the outfits, and all the moments in between. And if you want to see exactly how I styled each look, check out the individual styling videos where I break down the pieces, hacks, and thought process behind each outfit.
Because at the end of the day, personal style isn’t about having more. It’s about knowing what you have; and knowing what to do with it.
-Ash
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