If you’ve ever muttered to yourself, “What should I wear?” while deep diving into your closet, just know that you’re not the only one. This is a weekly conversation I have in my household when I’m seriously stumped. Yes, I live alone and like to think of these moments of dialogue as breaking the fourth wall. One of my resolutions to this eternal indecisiveness comes in the form of a camera roll folder including some of my latest outfits that are easily re-creatable. I decided to take my role as a fashion editor quite seriously and organize said iPhone folder into a shoppable story that we can both come back to for a reference when in need of some fresh inspiration.

Every time a new season arises, I find myself searching for wardrobe staples that are working double time to be both on-trend and timeless. I spent this fall searching high and low for transitional items that I can wear from now until spring, and I’m happy to be able to say for myself, so far so good. You’ll never be asking, “What should I wear?” again when you open your closet to find a plethora of ingredients to copy the outfit ideas that I created for us. Think sweater trends that have been chic for ages but are currently having a resurgence and a 2024 update on last year’s classic. Read on to discover the standout pieces I predict we’ll both be living in this winter.

My goal when getting dressed is to look like a fashion pro, and one of the best ways to showcase my skills is by having fun with layering. Nothing really makes a piece feel like your own than combining different textures and layers to create a look that’s uniquely yours. 

The powers that a cropped white button-down have are incredible.

A statement necklace you need to know about.

This vest is incredible.

Denim skirts forever.

This top can go from business when layered with a white blouse to a night out when worn solo—obviously I instantly added it to my wish list. 

For people who have shifted their focus from knit vests to one of our tailored favorites. The button detail on this top takes it to the next level.

Black and denim go oh so well together, and this vest is a great way to start making that pairing.

I need summer at the beach now.

The only thing I love more than this leather skirt is the tweed jacket that magically matches it perfectly. Patterned to perfection, this is a combination that I fully stand behind. 

This jacket is simply incredible.

There’s just something about this leather skirt that has made me fall in love.

Just put on these boots, and you’ll look dressed up—even in denim and a tee.

I own this and wear it often.

This shade of blue is unexpected for winter and very cool.

This jacket has been an editor favorite in our Slack conversations.

There’s something about the royal shade that is purple.

How incredible is this price point?

No matter how cold it gets in NYC, you’ll still catch me out and about wearing my favorite dresses with classic outerwear to match. To keep my legs warm, I pair my favorite midis with knee-high boots.

This is the wardrobe staple that I’ve worn over and over and over.

Officially the nicest coat that I own.

You’ll never regret buying a black handbag.

A classic black dress will always win me over.

This dress is giving me French-girl vibes.

This simple dress packs a powerful punch. 

There’s nothing more flattering than a bit of ruching. 

As we reach the thick of this mob wife era, we see everyone rushing to own a fur coat. For me, it’s always been an essential. Somehow my fur coat goes with everything, and it basically guarantees me getting a compliment, so I highly suggest giving it a try.

If you’re looking to take the phrase “mob wife” seriously.

I can never have too many simple oversize sweaters.

All about that flare.

When it snows, just wear a good pair of boots.

This coat would get me a lot of places.

I’m obsessed with everything about this look.

I can’t believe it’s under $100.