Bookworm Cottage Style

Since becoming a homeowner and dealing with other unexpected life expenses over the past year, fashion has taken a back seat to other budget priorities. I’m far more inclined to spend the small discretionary allowance I allocate myself each month on home decor purchases like a new nightstand or a new rug. Fashion is evolving at such a rapid clip for this elder millennial, that I feel like I kind of want to sit this wave out and catch the next one. You know what I mean? Like will I really want to wear mesh flats and barrel leg jeans in 2027?

I’ve accepted that many of the slim-fitting styles that were popular in the 2010s (my prime shopping years) and dominate my closet are suddenly very out, and have spent the past year selling, donating, and recycling too-small or outdated styles while I ponder what my wardrobe is missing.

The other factor keeping me from going all-in on current fashion trends is the second-trimester bump that is promising to emerge any week now. I’m not showing yet and am still in my regular clothes for now, but I have a feeling those days are numbered. As a first-time mom, I have no idea if I will carry large or small or how my body will change postpartum, so I’m holding off on investing in too many new clothes until my body reaches more of an equilibrium point.

Even though I didn’t prioritize fashion this year, I did add a few items to my closet. Here are the 12 items that made the cut.

1. Freedom Moses Slides: Believe it or not, this is probably the most-worn item of all of my purchases. I keep these by the back door and slide them on when I go to water the plants, check the mail, pick some herbs, or just putz around the property. I got this particular colorway on clearance at Saks Fifth Avenue because I didn’t want to pay full price for rubber sandals.  

2. J. Crew Heritage cotton Rollneck™ sweater in stripe: This 100% cotton sweater was a great purchase that I snagged during one of J. Crew’s many sales! It has a nice heavy weight to it, which is so important for New England weather. I wore this frequently throughout the fall and I know it will be in heavy rotation as we head into winter as well. The sweater has a generous, boxy fit, but the cropped length keeps it from becoming too overwhelming. The S is perfectly oversized on me.

3. Boden Chiltern Parka: Boston has cold, rainy weather that is hard to dress for. This parka has a sherpa lining and a water-resistant exterior. I purchased it in January and wore it often for the remainder of the winter. Although this exact style appears to be sold out, Boden is a favorite source for stylish outerwear. This British brand runs on the small side. I am in a US 6P which works with light layers, but a part of me wishes I sized up to an 8P to allow for my heaviest winter layers.

4. Banana Republic Chiara Cashmere Turtleneck Sweater: I bought the Banana Republic Chiara Cashmere Turtleneck sweater in a pretty lilac color on Black Friday a few years ago, and it quickly became my favorite sweater. I am a cashmere monster, and not all cashmere is created equal. This sweater is SO soft – truly the best! It also has a nice heavy weight that is perfect for those bone chilling New England winter days. Since these sweaters run $240 new and the style is no longer available, I have had my eyes peeled on the secondhand market for more colors at a more reasonable price point. When this Barbie pink number appeared in my Poshmark feed this year (at under $100, mind you) it was an instant purchase. No regrets – I’m loving it! It fits true to size – the S has a nice relaxed fit.  

5. Target Pleated Active Dress – All In Motion™: This was a total impulse purchase. I had been wanting a cute tennis dress to play pickleball in, so when a targeted Instagram ad brought this $35 dress to my attention, I promptly ordered it. I was able to wear it a few times before the weather turned. I sized up to a M for length/modesty (and because I have a long torso) but if I were to buy it again, I’d go with my true size (S) for a more supportive fit. 

6. Everlane Oversized Blazer: I had a couple of work trips earlier this year and felt the need to finally replace the shrunken blazers that dominated the early-aughts style scene with something more boxy and current. The Everlane Oversized Blazer was the perfect layering piece to pair with simple black trousers. Best of all, I was able to snag this one on Poshmark for a slightly discounted price. Although I haven’t worn it a ton, I’m glad to have something in my wardrobe that makes me feel confident and stylish in professional settings. It fits true to size. (I took a 4.)

7. Ann Taylor Gingham Maxi Skirt: I had been wanting some longer skirts, as I find them more comfortable to curl up in. This gingham beauty caught my eye on Poshmark and I’m glad I bought it. Although I bought in later in the summer and only had a chance to wear it once or twice before the seasons turned, I got lots of compliments on it and can’t wait to pull it out again. It fit true to size (I took a 4P.)

8. Old Navy Jean Popover Shirt Dress: This is an item that I haven’t really gotten my moneys worth on, simply because shortly after it arrived, the cold front swept in and bare leg season was over. Hopefully I’ll get more use out of this when the weather warms again because I love how the dress looks on other influencers like Abby and Joanna. I am hoping that this loose style will also be forgiving on a postpartum body. I took a S and it fit true to size.

9. Hill House The Cosima Nap Dress in Navy Stripe: A nap dress seems to be required as part of the basic pregnant millennial starter pack. This is the first clothing piece I bought after finding out I was pregnant, since it looked so cute with Mary’s bump. I have been gravitating towards longer dresses for the past few seasons and love the classic style of this navy and white striped number, which I cannot wait to wear not pregnant as well. When Hill House had a 30% off Cyber Month sale, I decided to take the plunge. We are deep in Boston winter so I haven’t pulled it out yet, but with a summer due date, I hope this dress will at least get me through my early third trimester. And just as importantly, I anticipate it being very forgiving postpartum as well. I went with my true (pre-pregnancy) size S.

10. GAP Maternity Inset Panel Cheeky Straight Jeans: I knew I’d need maternity jeans eventually, so I snagged these for a steal (under $30!) during Cyber Month sales. I haven’t worn GAP jeans in ages so I kind of guessed on sizing and went with my true (pre-pregnancy) waist size (27).

11. Madewell Maternity Over-the-Belly Kick Out Crop Jeans in Oneida Wash: Even though one pair of maternity jeans would honestly be plenty, I decided to buy one pair of the side panel style (the GAP jeans, above) and one pair of the over-the-belly style (these) since I didn’t know which would feel more comfortable on my body and if that preference would change over time as my bump grows. I don’t actually have a pair of kick crop jeans so I decided that maternity would be a great time to experiment with a new-to-me trend, and was able to get these during the Black Friday event for a discounted price. I went with my pre-pregnancy Madewell size (26P) and am hoping for the best.

12. The Great. + Eddie Bauer The Mac
My husband wanted to pop into Eddie Bauer to browse for himself, and yet somehow I was the one to walk out with a shopping bag. This rain coat from Eddie Bauer’s collab with The Great was the only one of its kind in the entire store and it happened to be a size S. I didn’t buy it right away, but I obsessed over it for two weeks and when I went back in and it was still there (and 50% off) I made my purchase. The S is quite oversized. Even over my thickest sweater it is plenty roomy.

As for my 2025 fashion wishlist? I have no idea what size I’ll be this time next year, so I probably won’t do too much shopping outside of the necessities. People rave about Lululemon Align leggings being stretchy enough for the 3rd trimester, and since I’m always looking to refresh my activewear drawer, I might make those a priority purchase. I’ve also been coveting the AYR Deep End top for years, and think that it has the perfect forgiving fit for second trimester, postpartum, and beyond. Finally, Lucie posted about wearing the same size pair of these chic Ann Mashburn kickflares pre-pregancy into third trimester. They’re a splurge but I have to admit that I’m tempted!