My Top 10 Outfits of 2019

I’ve been blogging about personal style for almost two years, but I don’t think I really hit my stride getting dressed until the late spring of this year. I took a look through all my outfit photos from 2019 in preparation for this post, but I didn’t see even one that I really liked until about mid-February. After that point, though, the frequency of outfits I like ticks up considerably.

There are many elements that factor into this nearly overnight transition from outfits that aren’t quite right to outfits I genuinely enjoy, but the number one thing that has made my wardrobe more satisfying is easy to identify: better clothes.

This is the first year that I went four seasons as a money making, brand-partnering blogger, and it shows. The money that I make from my day job is not enough to fund the kind of wardrobe that I want, and while I do pretty well with finding great pieces at low prices on second-hand markets, the truth is that I could not have the wardrobe that I have without the influx of high-quality gifted pieces from my brand partnerships.

A lot of bloggers have a guilt complex about this, but I’m not there anymore. I started this whole project with the goal of getting free clothes out of the deal, and I don’t feel guilty about that. When I decided to make this blog, I was unsatisfied with my wardrobe, and I knew that getting clothes the way that bloggers did was my best chance at being able to develop my style. I didn’t have a lot of money or an awesome camera or an Instagram-perfect lifestyle – I just had a love of writing and a knack for sharing my feelings with strangers on the Internet.

I was strategic from the first moment of it, and it paid off. I’m here. I have a closet full of beautiful things, good working relationships with some incredible brand partners, and an amazing community of kind, thoughtful, generous readers. I made some of the closest, most meaningful friendships of my life in this space.

The acceptable narrative for an ethical fashion blogger is that you just started doing this for fun, and your huge audience and closet full of gifted clothes were serendipitously bestowed upon you by happy accident. Your success, especially as a young woman, is so much more palatable if it was immaculately conceived. But make no mistake, I worked for this outcome from the very beginning, and the clothes hanging in my closet are my astonishing body of proof that I am capable of building something, all by myself, that other people find enough value in to pay me for. I will never feel guilty for that.

With all that said, I want to share my top ten favorite outfits of 2019 with you. I had so much fun getting dressed this year, which is such a far cry from the anxiety and dread that used to surround my morning outfit selection in my pre-blogger life. These outfits are in order from the beginning of 2019 to the end. In general I prefer warm-weather dressing to cold-weather dressing, and the favorites I’ve selected below reflect that. All of these outfits are made up of a combination of pieces that were gifted, thrifted, and bought new by me.

10.

Wearing: Coat Check Chicago Wool Bomber, Everlane Square Cashmere Turtleneck, Everlane High Rise Skinny Ankle Jeans, Everlane Day Heel.

There really aren’t a lot of outfits in my favorites list from the cold beginnings of 2019, but I just loved the combo of colors and textures in this particular outfit. These jeans don’t really fit me anymore, sadly. They stop showing up in my outfit photos about mid-year. (They are still packed away in my closet because I just love them so much I can’t bear to part with them. I will not pursue weight loss in order to fit back into them, but I recognize that my body goes through natural fluctuations throughout the year and they may fit me again as time goes by)

9.

Wearing: French Connection Elongated Bomber, Everlane ReNew Half-Zip Fleece, Everlane High Rise Skinny Ankle Jeans, Keds Champion Original Sneakers

This is my all-time favorite travel outfit and I repeated it many times throughout the year. My day job didn’t include travel until the very end of 2018, and then all of a sudden it included a LOT of travel, so having a travel uniform has made my life a lot easier. This jacket and these sneakers, specifically, are 2019 wardrobe MVPs that I never travel without.

8.

Wearing: Tradlands Elms Shirt, Everlane Track Shorts, Keds Original Champion Sneakers, Vintage Dooney & Bourke Crossbody, Ray-Ban Clubmaster Sunglasses

All of these pieces feel so classic and timeless, and as a person who generally hates shorts, I SWEAR by these shorts (Everlane discontinued them, but the Easy Chino Shorts are almost the exact same shape and fit). When I think about paring my wardrobe down to a super-small, essentials-only capsule, these all make the cut.

7.

Wearing: Everlane Go-Weave Essential Jumpsuit, Everlane Day Heels

As I’ve pursued a more minimalist wardrobe overall, one thing that was really important to me was finding an all-purpose fancy outfit that I could wear to weddings and events that would be appropriate in a wide variety of settings. This jumpsuit is that piece. I’ve worn it countless times over the past few months styled in so many different ways. And hey, if it’s good enough for Meghan Markle, it’s good enough for me!

6.

Wearing: Everlane Go-Weave Shirt Dress, Keds Original Champion Sneakers

I loved this dress as soon as I saw it on the Everlane website, but I was still surprised by how frequently I wore it this year. It just always seemed to be exactly the right thing. I’m wearing it here with my favorite little sneakers, but I’ve also worn it to work with heels, out and about in the summer with sandals, and even into the early fall with tights. It fits me perfectly and looks really great with my hair and skin. I was kind of offended when, almost immediately after its release, Everlane threw it in the sale section. This dress should be more popular than it is! It’s so good!

5.

Wearing: Wool& Brooklyn Wrap Dress

This is the dress that turned me into a Merino wool convert. Here I’m wearing it on the beach on Block Island, which is a small island a few miles off the coast of my home state of Rhode Island. Block Island is possibly my favorite place on Earth. It is so beautiful and personally so special to me in a way that’s difficult to put into words. When I go to a special place like that, I like to wear an outfit that honors that feeling. This wool dress was the perfect thing to wear on a special day. Style-wise, I felt pretty and I felt like myself, and practically, for a day of swimming, biking, exploring, eating, and boating, I could not have asked for a better outfit. I was cool and dry the entire day while my friends mostly sweated through their clothes. I was also the only one who didn’t have to change for dinner!

4.

Wearing: Tradlands Modern Fisher Sweater (Cotton), Blake Goods Center Bar Belt, Everlane Corduroy Stamp Skirt, Nisolo Mariella Mules

This was just a fun outfit and every time I look back at it I smile and think, I should wear that again. I’m adding this belt and this skirt to my short list of 2019 wardrobe MVPs because of how dramatically they expanded the rest of my wardrobe. I wear them both constantly, and frequently wear them together. Also shoutout to Tradlands because this sweater is so beautiful and luxurious I don’t feel like I deserve to own it.

3.

Wearing: Everlane ReWool Overcoat, Everlane Cashmere Crew, Everlane Ponte Pant, Keds Original Champion Sneakers

I wrote up a full review of this coat earlier this year, but I’ll just say again that a long wool camel coat was on my wish-list for a long time, and once I finally got my hands on one, it did everything for my wardrobe that I hoped it would. It’s my “fancy” coat for the office, but I loved the way I styled it on this day, casually with a sweater, slim black pants, and sneakers. I feel like a cool Scandinavian minimalist in this outfit (and yes, I am always trying to channel either Signe or Lee no matter what I’m wearing). I hadn’t really gotten a hold on my cold-weather style at the beginning of the year, but I feel like I’m finally starting to get into a good groove with it now.

2.

Wearing: Everlane Cashmere Mockneck Raglan Sweater, Everlane Ponte Pant, Everlane Day Glove

Speaking of getting the hang of warm weather dressing: this outfit. After dying my hair blonde, I parted with most of my orangey-brown wardrobe items, but I was still craving warmer tones to compliment my otherwise black and white wardrobe. Enter this chocolate brown hue. It’s cooler than the toffee-type colors that are popular right now and has such a lovely richness to it that I think works much better for my current hair/skin situation. Color aside, I also really loved this outfit because of the simple but elegant silhouette. I crave comfort more than anything else in winter dressing. I felt professional and put together in this, but also like I could move around in it completely unrestricted. I would really like to pick up this same sweater in cream.

1.

Wearing: Elizabeth Suzann Rhodes Mockneck Sweater, Elizabeth Suzann Cecilia Pants, Everlane Day Glove

I saved the best for last. If you follow me on Instagram, you’ve already seen this picture and you know a little bit about the story behind this outfit. A few weeks ago, I got an email from an amazing reader who I now think of as my Fairy Blogmother. She mentioned in her message that she enjoyed reading my blog and that she had a collection of Elizabeth Suzann clothing in her closet that she wasn’t really reaching for. She asked me if I wanted them. As a gift. No strings attached. Just because she is kind and she knew I would like them. I’ll tell you guys what, I was Christmas shopping in Barnes & Noble when I got this email and I literally had to sit on the floor in disbelief for a few minutes while I read it over again and again. It was so unfathomably generous, I really couldn’t believe it.

So, this outfit, and all the outfits of ES pieces I’ve worn since, have an extra special place in my heart, not just because they’re beautiful and from a highly coveted ethical fashion designer, but because they remind me of this wonderful reader and how much her kind words and incredible gift meant to me. I wasn’t in the best place creatively when I got her message, but it was a spark of encouragement that I needed to keep going and keep trying things in this space. Thank you, D. I hope you’re reading this right now and I hope you like this little outfit I came up with. It makes me feel like a million bucks.

That’s it for my favorite outfits of 2019. I have some other reflections on the past year and some thoughts on the year ahead that I’ll save for a future post, but I hope you enjoyed this one! Thank you to everyone who reads this blog. It means so much to me that you continue to stick by me through dusty mirror selfies and inconsistent posting schedules.

If I don’t post again before the end of the year, happy holidays!

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This post contains affiliate links and some gifted items. All opinions expressed are my own.