Every year I whine about the end of summer as soon as August rolls around. It seems like everyone jumps onto the Fall style bandwagon and begins chatting all about and sharing pieces for the cooler days ahead. Half of me watches in horror — it’s still summer through most of September after all, and here in New York it stays just as warm for most of it. Why look at things I won’t be able to wear until November now? The other half of me is right there with them, over the heatwaves and mosquitoes and sticky evenings and ready for non insect driven sartorial choices.

When it comes to Fall style and dressing myself for the season I tend to keep things very simple. Back in the days when commuting to an office setting was in the cards I would wear dark jeans in blue or black, often with an oversized top or sweater in a French tuck and ankle boots or flats. It’s a look as basic as it comes. As I’ve mentioned a bajillion times, I am a collector when it comes to my closet. I look for pieces that I intend to love forever that can be paired with different things to keep them fresh through the years. This means I tend to limit more trendy pieces from entering the rotation, which is fine but it allowed me to fall into a bit of a rut. I stopped wearing dresses because it felt easier not to. And heels higher than 2 inches. A lot of self imposed style limits. I shared a lot of my daily looks on my Instagram stories and it quickly became very clear how boring they all were and so I put a pause on that.

I keep thinking about this one outfit I wore on repeat back in Winter 2010. It was a knee length forest green Susana Monaco dress with an empire waist — hear me out. I paired it with a black cardigan, belted at the waist with a braided skinny belt, and my favorite Michale Kors knee high heeled boots that I found one sale for next to nothing at a Saks outlet and wore until the soles needed replacing. I still have them by the way, they just aren’t as comfortable after having been resoled. Is it a look that I would still wear today? Probably not. But at the time I loved it. It reminded me of Emily from The Devil Wears Prada and made me feel very cool and stylish and that’s the important part. Very different than the sour taste I get in my mouth when I think about the black plaid top I bought from Madewell in Charleston and paired only with black jeans in 2017 (pictured here). It’s still in style and I hate it.

I spent last Fall pregnant and working from home so I pulled out all of my dresses again and purchased a few more fun pieces like this tweed pinafore, cropped t-shirts, and a few more colorful options for sweaters and dresses. Color is something I had been shying away from too. This fall I am not pregnant, am still working from home, and am feeling inspired to start dressing more like my old self again and less like I need to be convenient. This summer I purchased a few new pieces for myself that got me feeling more like my old self — those early post grad days when I would experiment with different combinations and wear things that made me excited. The version of me that once emailed Rag & Bone on Christopher Street immediately after an email newsletter to inquire about the jacket featured because I could not stand to wait until the weekend when I could get to the shop — I liked her, I liked me this summer. Let’s run with it.

Does this mean I will refuse to wear the aforementioned basic sweater, jeans, ankle boots combo?
I would love to say yes, but with a little one in tow I know that I will panic dress myself in this look.

Do I still love and gravitate towards neutrals?
Yes.

Will I still purchase mostly white items of clothing?
Probably.

Will my personal style all of a sudden become dramatically different?
I still wear that Rag & Bone jacket, so no.

Will my philosophy on forever pieces change?
Please see previous answer.

So this season — I have done a little Pre-Fall browsing, trying to come up with my overall goal and have found some very good pieces that I am so excited about.

01. A black check print that doesn’t make me want to gag. Oh my goodness the back on this thing! Impractical? Sure. I want to wear this with a visible cross back sports bra and loose leg white denim.

02. A belted shirt jacket. I really like the shirt jacket trend — even if it gives heavy dad vibes, which had me initially hesitant. I bought my first shirt jacket last year and wore it so much throughout the winter. It even fit my bump for the bulk of my pregnancy, which was great! Now I like the belted aspect a lot, especially on these two because it gives a more flexibility and a more feminine flair.

03. Fitted square neck tanks. I have two of these, one in white and one in black, and they have quickly become my go-tos and are probably my most worn tops. When I was pregnant I just popped an open shirt over top. All summer I’ve been living in them solo with denim shorts or loose leg linen pants. It’s funny because before pregnancy I would shy away from anything fitted and feel so insecure about how I looked. I am so impressed with how much grace I have given myself throughout the whole process and postpartum period. It is in my nature to be overly critical of myself, but now I am so appreciative and accepting of my body that I no longer mind. I plan to pick up a few more of these, maybe even in different colors!

04. Quilted jackets. I bought this one from the Nordstrom Anniversary Sale, and this one for Eleanor to wear to match, but I’ve just spotted this one which has a closer pattern to the one I bought for E and now I am seriously questioning whether or not two green quilted jackets is too many, ha! I also love this white floral one. It’s on my birthday wishlist.

05. I am very into cardigans again. Especially boxy ones that look a bit more like jackets like this. I went through a phase somewhere between 2015 and 2019 where they felt gross. Now we’re back, as long as there is a bit of structure to it.

06. Now let’s chat dresses and skirts. When it comes to dresses, I have my eye out for more fitted pieces that hit above the knee. Nothing too fitted though. Prints and and colors welcome. Think this Veronica Beard sale steal. And skirts, I’m thinking silky midis with good flow that I can pair with these fitted tanks. I have not been able to stop thinking about this soft yellow beauty.

07. And finally, pants. Tik Tok says skinny jeans are out and I kind of agree. I have been loving a more relaxed fit when it comes to denim and have purchased wide leg pants for summer for the last two years. No new Fall/Winter denim has made it into my wardrobe yet as I wasn’t about to buy new jeans with a bump not knowing what my body would look like postpartum, but I have had a few pairs saved to my wishlist that all follow this concept. I last purchased jeans summer 2019 so my wardrobe needs a big denim update stat. It has been too long!

That’s all for now. I have started my Fall and Pre-Fall style boards, the latter of which you can find here, and will continue adding pieces that catch my eye as we go.

Now please tell me — what are you excited to wear this Fall?