Everyday Transitional Winter Dressing
No. 92 - An effortless outfit recipe
Welcome to Style / Substance – Your weekly dose of personal style and confidence + analyzing the cultural influence of aesthetics and the psychology of what you wear and how you show up.
Here to make your life easier and help you present your best self, inside and out. If you enjoy this week’s post, don’t forget to tap the ❤️ above – I sincerely appreciate your support!
A client and friend of mine has what she refers to as her “February sweater.” It’s precisely what you think it is: a sweater she holds out to wear until February, signaling the tail end of winter and that she managed to make it through the bitterness of the season. It’s her visual cue that she has to cozy up just a little longer.
In the spirit of February sweaters, I’ve compiled the components of a transitional winter look that will carry you into the days when the buds begin to bloom. Whether this is casual office-appropriate, coffee meeting or carpool, or weekend-vibey, you can’t go wrong with the simplest of elements.
Here’s the doable recipe:
Start with a pair of jeans or semi-casual pants (like a chino, cords, or even ponte) that are slightly cropped so they don’t “break” at the top of the shoe/ankle, but are long enough so that a bootie comes up ever so slightly under the hemline of the jeans when you’re standing (appx 1” hem over the top of the bootie shaft is an ideal overlap). Straight leg, girlfriend, kick crop, wide leg crop, and barrel leg are all great options. Do the sit test before you walk out the door so that you know when you’re seated throughout the day, you’ll feel comfortable in them.
Some jeans/pants I’m loving/recommending:
Kut From The Kloth Reese High Rise Ankle Straight Leg // Generally recommend sizing down one size in this brand.
Madewell Kick-Out Crop Jeans // True to size.
Mother Twister Flood Ankle Flare Jeans // True to size.
Gap High-Rise Kick Jean // True to size.
BR Corduroy Barrel Pant // True to size.
Next, pick your shoes — depending on the temp outside, what the ground covering looks like (snow, mud, slush, etc), and what your day entails, try a bootie (see note above about making sure there’s an overlap from the pant to bootie top) — if you want to level up your winter shoe game, layering in suede or a lug sole style can give you a little extra character. Or, go for a fun trainer sneaker with personality (not your actual fitness shoes).
Look out for this coming Saturday Styles newsletter with all my go-to bootie recs.
For sneakers, I’ll do an edit this spring, but to hold you over, these have been the root of my sneaker problem ;) Be sure to half-size down.
On top — enter your February sweater. Some folks like crews, other v-necks, whatever it is, make sure it’s soft, classic, and slightly fitted. If you respond well to vibrant colors (ahem, dopamine dressing) then bring them into the mix. Be sure you’re keeping your knits in good condition; you’ve been wearing them for a few months now, after all.
The sweaters I’m wearing in the snaps above:
Favorite cashmere crew (similar)
Luxe cashmere half zip (similar)
Accessorize minimally — It doesn’t take much to round out this kind of everyday transitional look. In fact, less is more. Keep the jewelry light and easy to put on/off (think studs or small hoops and delicate layering necklaces, or thin stacked rings), try a belt for some personality (though you can wear pants with belt loops without a belt), add a hat with something clever or personal on it (like I do when I don’t wash my hair), and make your bag an easy crossbody or grab-and-go shoulder sling/tote.
For fun:
My hat says “NAP” a play on GAP by OJM.
This bag has two sets of straps that make it go from crossbody to short, going-out shoulder style.
The belt is a staple.
I’m frequently asked about styling and what the core elements to building an outfit, and at the end of the day (or start rather), it’s all about incorporating the pieces that you love and make you happy. And from there, you start to discover your style by trying things out. You have to put the clothes on in order to know, so why not just try?
+ Speaking of trying… I am inquiring in a new way and welcome your feedback in this quick poll:
🧠 What Are You Reading?
Last week, my graduate semester began. I’m in the inaugural “Women’s Brain Health” course at Harvard. I shared some of the required reading and the bonus books that are in my stack for the next few months. My mind is already exploding with all the fascinating research and stories, not to mention just how little data we actually have on women’s health (which I’ve known, but this class is a more detailed stark reminder). I wanted to reshare the post with you in case you’re not on socials and/or you wanted to bookmark some of these fascinating reads…
📚 Have you read any of these books? Would love to hear from you if so! And what good reads are on your nightstands right now that you’re devouring?
The Menopause Brain, by Lisa Mosconi, PhD
The Brain Health Kitchen, by Annie Fenn, MD
All in Her Head, by Elizabeth Comen, MD
The Lady’s Handbook for Her Mysterious Illness, by Sarah Ramey
Beyond Anxiety, by Martha Beck
All Fours, by Miranda July (this one’s for brain breaks ;))
📲 Know someone who would enjoy this newsletter? Style is for all. Spread the love and share with them.
❣️ Short + Sweet V-Day Gift Guide
For those of you who like to celebrate the heart-filled days of February, here’s a favorite hit list of gifting ideas. I even chatted it up with my friend Adam Foster about an earring concept to help you elevate an existing pair of studs if this is your love language.
