Earlier this year, I compiled a “Top 5” of the pieces I’d found myself putting on over and over again during the course of the winter. The list was short and comprised of some super classic, wear-with-everything pieces that were my wardrobe workhorses: things like my a leather jacket, camel coat, and black booties.
Fast forward seven months, and I’m revisiting the post today with a bit of an update. While what I’m wearing the most these days largely remains the same, I’ve been thinking more about exactly why these particular garments earned that place in my wardrobe. What characteristics do my most worn pieces have that make me reach for them so often? I came to this consideration because I know that although something might work well for me, it won’t necessarily work well for others – and I’m increasingly disliking the idea of lists of must-haves, since it doesn’t do much to account for personal style.
That being said, I’ve updated my Top 5 for fall — by expanding the selection with more general guidelines of why I wear something often — in hopes that you might be inspired to find the equivalent of what could work for you. I’ve also added some personal favourites (many of which happen to be on sale over the next few days on Shopbop) at the bottom of each category!
One | The Jacket That Pulls Everything Together
I remember reading an article on a style site a long time ago about the “rule” of a 3rd piece, and how topping off your outfit with a third or fourth garment does wonders to instantly make an outfit more stylish. It made a lot of sense to me: I’ve seen how much adding even a simple cardigan to a silk cami and jeans can contribute to a look, and when I admire someone’s style it most often involves the ability to layer well.
Because of this, I tend to like investing in jackets that are classic, versatile, and high quality, because it can do so much to pull together even the most basic combination of pieces. I tend to prefer jackets that are fitted in the arms because they streamline my silhouette no matter how much I layer on.
Two | The Top That Goes With Everything
For whatever reason, my collection of tops is by far the smallest out of any type of garment in my closet. Maybe it’s because I don’t want to spend money on something so basic, but I’m also quite satisfied with what’s already in my closet. A few simple top in versatile cuts that pair well with a variety of bottoms and jackets is really all you need.
I veer away from super trendy tops and go extremely basic in this realm: neutrals, very few details, and good materials that will hold up well over time.
Babaton | A simple cropped top that adds neckline interest for all sorts of jackets
Everlane | A well-priced, well-made silk button-up that can be tied for different look
Madewell | My favourite simple cotton tees (20% off w/code EOTS17)
Cuyana | A three-ply silk to elevate the simple tee
Three | The Shoes That I Can Actually Walk In
Five years ago, my shoe closet was filled to the brim with 4-inch heels that, in the end, I could only comfortably wear for photos or during very short walks. Things have definitely changed the most here thanks to age and my “problem feet” catching up to me. The shoes I’m reaching for these days are the ones I can actually walk in. I now choose my footwear based on how much I’ll be on my feet on a particular day, and plan my outfit around that.
In my current rotation are my Acne Studios Jensen booties, my white Frye sneakers, my Everlane slides, and Everlane oxfords. Although I’ll always like black, I do feel like wearing lighter coloured footwear like beige or tan do wonders to elongate my legs.
Acne Studios | the most beautiful and classic pointed chelsea boots
Frye | white leather sneakers that are comfortable, minimal, and sleek (20% off w/code EOTS17)
Everlane | menswear inspired oxfords in a feminine blush
Everlane | wear-with-everything slides that add polish to everything
*note: all of my Everlane shoes have taken a bit of time to break in, but have gotten so comfortable with wear.
Four | The Pants That Fit My Body Perfectly
The pants I wear are the ones that fit me well. I have athletic thighs, large calves, and a comparatively small waist, so it’s always been a challenge to find bottoms that I feel great in and can actually freely move in! I’ve tried on so many pairs of pants in my lifetime and so few have worked, so I’m not averse to buying multiple colours of something that’s perfect.
I like my bottoms high-waisted these days because it highlights the smallest part of my frame and also helps hold everything in! I also hem my denim to be above the ankle bone because I think it looks the best on a petite frame.
L’AGENCE | my favourite high-waisted black skinnies of all time (20% off w/code EOTS17)
L’AGENCE | I like them so much I have them in blue, too! (20% off w/code EOTS17)
Wilfred | everyday, dress-up-or-down trousers
Wilfred | a wide-leg crop for a bit of a different silhouette
Five | The Bag That Adds Polish to Any Outfit
For as long as I can remember, my favourite kind of bag has been minimal, simple, and structured. I appreciate how it can make everything look more polished, even if I’m just wearing blue jeans and a white tee. I’ve have a few non-black bags, but always find myself reaching for the same ones over and over again.
If you’ve been reading my blog over the last year, you’re probably either super sick of this A.P.C bag, or maybe you’re convinced that you should get one too (I just realized it’s basically in every photo featured here!). It goes with everything and – I’ll be honest – makes me feel a little bit cooler than I actually am.
A.P.C | my everyday go-to (20% off w/code EOTS17)
AESTHER EKME | a crossbody for the ultra-minimalist (20% off w/code EOTS17)
The Stowe | another half-moon bag that’s simple and stunning (20% off w/code EOTS17)
What are your favourite pieces in your closet, and why do you like to wear them?