My Favorite Looks of 2023

What I wore, why it worked, and what I learned about myself

If you did any traveling this holiday season, you may have engaged in a classic millennial airplane activity: the camera roll purge. You probably don’t have 29,010 photos like I do (insane, I know) but it’s always fun to peruse the highs and lows of the past year. As I’ve been reminiscing, I’ve been thinking a lot about what I wore throughout 2023. To get a better idea of how my personal style evolved, I decided to find my absolute favorite outfits from the year and put them all together. While I was definitely expecting to see some througlines, I was actually surprised by how easy it was to identify my favorite fashion elements in all of these looks. There are plenty of things I know I like, but seeing them arranged like this really made my aesthetic visually clear in a way that can be hard to see otherwise.

I’m sharing my best looks, and some thoughts on how and why they worked for me. I hope you’ll find some inspiration here, not just in my personal style but in using this reflective approach to better understand your own!

Look #1: 60’s pleated dress, Simon Miller pleated crop pants, and a vintage silk chiffon dress worn as a duster

The same outfit in June and October

Starting off strong with a personal top contender. I wore this outfit the first time with an old pair of faux tortoise sandals, and the second time with red Charlotte Stone clogs. I prefer the look of the sandals as it creates a sleeker line at the leg, but the clogs were more seasonally appropriate and better for standing all day the October Vintage Show.

Why it works: I really wanted to wear this dress but was worried I would be chilly, so I added the pants and duster and it all really clicked. I know a dress over pants is a widely lambasted fashion choice, but I think layering pleats over pleats creates a cohesion that the 00’s pants/dress combo is often missing. The sheer duster served multiple purposes here: it added texture and color, lent a sense of lightness to balance the heavy looking pants, and covered up the fact that this dress is a bit too tight around my arms.

Look #2: Online Ceramics t-shirt, lace Only Hearts dress, tan bike shorts, black cowboy boots (eBay), and a very tired Gordie

If I had to pick a personal quest when it comes to fashion, mine might be “How to Wear a T-shirt, but Make it Fashion.” This is a very rare look that includes no vintage! Okay actually the boots are vintage, and some of my jewelry always is, so I’m never truly in no vintage. But this is as close as it gets.

One thing I leaned in to this year was my love of a white tee. In the past, I felt like I was supposed to branch out by buying and wearing t-shirts in different colors. White tees felt safe and kind of boring, and were way more prone to discoloration and dinginess from frequent wears and washes. But regardless of how many cute colorful tees I found, year after year, my white shirts were the ones that ended up back in the hamper every week. Since I’ve shifted to pretty much only buying white graphic tees, I’ve found that I’m actually avoiding ruining them because I have so many more options in my rotation.

Why it works: This outfit gives me all of the comfort and ease of a loose tee and bike shorts, but made me feel stylish instead of frumpy. I wore a few variations of this throughout the summer with different t-shirts and sneakers instead of boots. It’s casual, comfortable, and cool (literally and figuratively), which is really all I can ask for on a hot NYC day.

Look #3: 60’s chiffon wrap duster, very old black Forever 21 crop top, very old sheer Free People dress, 90’s Pleats Please pants, and thrifted Ferragamo bow flats

Following the 2020 lockdowns, the fashion world saw a big surge in bright colors and bold prints. It felt like everyone was eager to come back out in a swirl of sartorial confetti, with sweatpants and all-black ensembles banished to the world of “before.” I found myself extremely uninterested in my black clothing for the first time since middle school. A head-to-toe black outfit felt stifling and stale, and I had no idea what to do with the dozens of black garments I had amassed over the last decade. In the years (can you believe it’s been years?) since, I’ve found my sweet spot: black maximalism. I’ve found that I actually love all-black outfits again when I lean heavily on texture, kitsch, and lots of layers.

Why this works: wearing all black, or almost all black, gives you space to get really creative without coming off confused or chaotic. This look combines polka dots and ruffles (the sheer dress is a swiss dot with a ruffle hem), pleats, a crop top, chiffon, satin, a campy statement bag, and a very chunky vintage glass necklace. Both the tie on the duster and the shoes add bows. All of these together would typically be more over-the-top than I’d go for in a colorful ensemble, but felt comfortable and chic in all black.

Look #4: 60’s feather-trimmed robe, 70’s-80’s ILGWU tee, 70’s Levi’s plowboy flares, old Jeffrey Campbell boots

A Vogue.com certified fit! This photo was taken in February on the first day of my first Manhattan Vintage Show, making it a very special and affirming way to start my year.

Why this works: Another example of T-Shirt, But Make It Fashion! A great tee and great jeans are a truly foolproof combo, I usually just add one statement piece to bump the whole look up a notch. I usually add a fabulous jacket, in this case a feathered vintage robe. A similar effect can be achieved with some statement jewelry, bold shoes, or even a cool hat. Well-fitting jeans are a key part of making this simple look truly stylish - I had these jeans tailored at the waist and hips.

Look #5: 90’s Strawberry Festival tee, 90’s strawberry jacket, thrifted red silk slip as a miniskirt, black cowboy boots, strawberry earrings

Another full look that I wore on two separate occasions! Featuring yet another graphic white tee. I don’t have any close up photos, but I was also wearing life-size rubber strawberry earrings to really lean into the theme.

Why this works: I clearly love a strawberry motif, but had never actually thought to pair all of my strawberry pieces together! This look is super matchy in color and theme, but maintains a level of contrast because of the various different textures. I jacket is seersucker, the skirt (dress) is silk satin, and the boots are leather, which I think helps the on-the-nose vibe from falling flat or looking too costume-y.

As you may already know, I got married this year! Alex and I tied the knot in Vegas, which included a full weekend of festivities with our friends and family. Three of my favorite looks of the year were from our absolute dream of a wedding weekend.

Look #6: 90’s yellow paillette & bead mini dress, 60’s yellow peignoir, and thrifted metallic pink heels

My husband and I had a combined bachelor/bachelorette two days before our wedding, and all of our guests were invited, including our parents. Our very PG-13 bowling alley party was unconventional and so much fun. I definitely wouldn’t describe my personal style as sexy, so this dress was definitely more form-fitting than most of my outfits are. I taped my boobs for the first time ever and let me just say, the girlies were standing on business. I did rip off all of my nipple hair later, but it honestly may have been worth it.

Why this works: I really wanted to wear sequins at least once during our Vegas weekend. I also wanted to include my Susan Alexandra Merry bag into one of my outfits because it’s the first gift Alex ever gave me when we started dating in 2018. Major green flag!! I wore plastic dice earrings to match the bag and lean into the camp factor. I didn’t want to wear white all weekend, so this look really wasn’t bridal at all. The dress was definitely more “bachelorette” without the peignoir, but it all felt so much more me with that little vintage grandma touch.

Look #7: 40’s satin rayon gown, Mary Frances bead & rhinestone heart bag, 60’s heart charm necklace, old Jeffrey Campbell mules

The evening before the wedding, we had a dinner with our immediate families. Our parents met for the first time that weekend! I bought this 1940’s dress from my friend Karina of Lunar Curated, and decided it would be my “second” dress, even if I was wearing it the night before. Our ceremony was quite literally five minutes long, so it wouldn't have made any sense for me to change on our actual wedding day. I’ll admit, I actually like how I looked in this outfit more than I did in my wedding dress. That being said, I wouldn’t have changed a thing! It just means I wore one more fabulous outfit.

Why this works: I absolutely love the way this dress fit me - vintage bias cut satin really hits different. I wore Spanx shorts underneath specifically because we were taking photos with my wonderful friend Kathryn (who crushed our wedding photos, clearly) and they were actually a lot more comfortable than I expected. My necklace is 60’s brass that I found on Poshmark that has a dozen or so different heart-shaped charms, which of course matched my giant heart bag. The accessories added my signature campy touch to an otherwise very sleek and elegant look.

Look #8: 50’s feather-trimmed dress, JW Anderson silver spiral heels, custom faux wedding cake purse, thrifted veil

I think it’s pretty unusual for the dress to be the easiest part of your wedding look. I took one look at this 1950’s dress on Singulier MTL’s website and placed my order. I knew Alex had my ring, but he hadn’t even proposed yet! Ordering online was a risky move but I was confident in my measurements, and sure enough it fit like a glove. Fast forward two years and the dress was a bit too small by the day of, but I didn’t even consider any alternatives. Was the dress perfectly smooth in the photos? Nope! Was I even thinking about any of that while I was marrying the love of my life? Nope!

Why this works: I’ve never invested in the idea that your wedding should be the best day of your life, or that you will look more beautiful on your wedding day than you ever will or have. I don’t believe either of those things are true, and I don’t think you should want them to be! Marrying someone genuinely wonderful means that your wedding is just the first of countless more best days ever. And I couldn’t have been at my most beautiful on my wedding day, because I’m still getting prettier. What could possibly be more beautiful than the honor of living and experiencing and aging?

When I look at our wedding photos, I just think about how I couldn’t stop giggling. I felt so happy, so loved, so sweaty, and it couldn’t have been more perfect.

What I learned about style in 2023…

One of my biggest fashion accomplishments this year was the number of times I re-wore the exact same outfits, head to toe. It’s one thing to re-wear the same pieces, but it’s hard not to hear the “outfit repeater” sentiments of my teenage years when I put together a fully repeated look. Outfit #1, for example, was created for a party for Manhattan Vintage Show dealers. In the past I would have worn it again to see non-vintage friends, but wouldn't have worn it to the Vintage Show because I’d be seeing the same people as the first time. But this year I did it, and guess what? Nobody gave a shit. They also probably didn’t remember, because it had been four months. I felt just as good in the outfit as I did the first time, I heard just as many compliments (or more!), and it helped me break the ice with so many new people. If it works, it works! So wear that outfit again. It’ll be great, I promise.

Things I love: long sheer layers, the color green, a white graphic t-shirt, heart shaped everything, pleats, feathers, and statement bags.

Things I’m (hopefully) leaving behind: thinking I couldn’t pull off bangs, worrying about why people on TikTok hate a dress over pants, colorful t-shirts, being self conscious about taking my photo in public.