The Seven Styling Tweaks You'll Want To Commit To Memory
Cuffing, tucking and tying à la Kelly Klein.
January is SHOP YOUR WARDROBE month over on ‘The Wardrobe Edit’, a four-week-long content calendar that perfectly aligns with a January ‘no-buy’ or if you want to take a moment to press pause, reconnect with your wardrobe and fall back in love with what you already have. To gain full access to all the posts, you can upgrade to a paid subscription (THANK YOU!) with a limited-time 25% off! Along with all the content I post this month, you’ll unlock over 350+ posts, stacked with styling ideas, tips and formulas…
Next up in my styling session series is the debrief from my hour spent with Kelly Klein (read about my brain-altering session with Reva here and Anna, who came with all the cool girl colour combos, here). Miami-based and New York-born, Kelly exudes that effortless vibe. A little boho, a little vintage and a former Head of Merchandising at Veronica Beard and DVF, she just gets style. From spending yesterday afternoon with her (I did the ‘Personal Styling’ package available to book here, $300 for 1 hour), I can also report that Kelly is going to brighten your day and be your number one hype-woman. She’s warm and kind and instantly put me at ease. She also has the KNOWLEDGE!! So much so that I was typing notes as we went because I knew you’d want to hear what she had to say. I was like, “Kelly, were you a Teacher in a previous life?! Her ability to explain the hows, whys and concepts made our short time together invaluable, so here’s the beefed-out version, along with accompanying visuals, of the notes I made.
Pre-session, Kelly asked for a moodboard, and I sent her over the following, explaining that I was in a pretty neutral mood currently. With my main aim being to find outfits for those in-between moments; errands, pick-ups, weekend playdates, coffee with friends, etc.

What I found really helpful was that Kelly ran through her observations from my moodboard at the beginning of the session. It was so handy to have an expert pull apart the common threads:
Coats are my anchor piece, pulling the whole look together.
I like elongated lines in my outfits.
Interest tends to come from texture - leopard, leather and suede - and almost replaces colours in a way.
I enjoy masculine silhouettes over outfits that feel more feminine.
I like the peek of an ankle or a wrist. Kelly called this ‘body contouring’, as it draws the eyes to the smaller parts of our bodies, balancing our look when we wear more oversized pieces.
SEVEN STYLING ADJUSTMENTS TO REMEMBER
The true genius of Kelly lies in the way she manipulates clothing (and can do so virtually!). Cuffing, tucking, and tying are her styling superpowers; how to make the piece drape just right for your body. I mean, her IG bio is ‘I write a newsletter on rethinking and maximising your wardrobe’ - she’s not wrong!! It was learning these small tweaks and adjustments, and her clear explanations on why they help an outfit click that were the true wins of our session for me.
I’d spotted this technique on her Substack notes last month, but having her talk through it in real time was extremely helpful. Two things to note:
When you tie a jumper over your shoulders and fold down the collar to create a flat edge, keep the collar exposed (instead of having that side against your back). Kelly explained ‘show off that collar construction!!’, there’s less concealed bulk this way, too.
Then, when you tie it, take the arm that’s flopping over the top of the knot and throw it over your shoulder. The arm wants to sit in that direction, so it stays in place and the shape it creates frames the face.
Kelly is the Queen of the jumper tuck. Her advice? Tuck where one of your belt loops sits (so off-centre), jam it in, and pull it out. Just like she said in my ‘24 *Very* Stylish Substack Writers On What They Do When They Have No Idea What Wear’ post:
Once the bottoms are on, the outfit clicks when you reveal a small sliver of your waist; even an inch is enough. That can be with a small front tuck, or lifting the hem with a clip or brooch. Avoid full tucks. Bringing the eye up to the narrow part of the waist keeps proportions balanced and makes even simple outfits feel pulled together.
I’d sent Kelly my Indyx Open Closet, so she could see everything in my wardrobe at a glance (another digital wardrobe pro!), and she’d spotted my plaid flannel shirt and suggested I try tying it around my waist to break up a simple, but sometimes boring ‘jeans and jumper’ formula.
First, open up all the buttons of the shirt.
Just like with jumpers, create a flat edge by folding over the collar, but leave the collar side facing outwards once you tie it around your waist to show the shirt's shape.
She suggested double-knotting it so there wasn’t so much sleeve dangling down (game-changer!!).
Pull the knot slightly to the side so it’s a little off centre, and then fuss around with tucking your jumper over the top and draping it how you’d like.
Two quick tweaks:
Pull your jumper sleeves out so they peek out from under the sleeves of your jacket or coat. A small detail that can add contrast.
Cuff your trousers or jeans - it can completely change the shape. Cuffing my vintage Levi’s 501s made them feel a little more feminine and showed off my sheer sock/flat-shoe combo, which added more texture to the outfit.
Kelly asked if I had any scarves. I answered that I owned just one. Her answer? Good! Just use your jumpers as scarves - don’t bother buying a load of scarves in different colours. This is something I do quite often out of necessity - one scarf, remember! But one thing I don’t tend to do is wear the same colour as what I’m wearing underneath, but I loved the grey-on-grey when we tried it. Opting for a lighterweight grey V-neck, with a chunkier grey jumper over the shoulders.
You know how a summer bag is a great contrast to an oversized winter wool coat? Almost the bag version of Allison Bornstein’s ‘Wrong Shoe Theory’. Well, Kelly suggested a similar thing, but for beaded necklaces, which are a category in my jewellery box that tends to gather dust. They juxtapose well with knits, even if the necklace is tucked under the neckline and only a sliver of the beads peeks out.
NOTES ON STYLE THEORY

As I said, I made notes in this session and a load of them. So here are some more styling titbits that Kelly dropped along the way:
If you’re building an outfit from a function-first perspective, then shoes are the logical starting point.
When you’re trying to work out an outfit for those ‘in-between moments’, find one polished thing - like my leopard print coat above - and tone it down with something super chilled, like my Midimalist tote.
Having a throughline can really help an outfit feel ‘right’. One colour, or a detail that repeats at least once. For example, we made a lot of looks that featured my black loafers, a black belt, and my vintage necklace, which is also black.
The finishing touches are what make the outfit you. The one pair of sunglasses you always wear, your favourite watch, your usual earring or bracelet stack. Those signature pieces add personality.
In case you don’t have a full-length mirror at your disposal, Kelly takes screengrabs during the session and adds them to a shared album for you to reference after. We made so many looks! We could have kept going, but my 5:30 pm dinner deadline was approaching (small kid dinnertime!!), and chicken wraps called. Last night I went to bed with a full belly and a brain swirling with styling ideas newly committed to memory. Thanks, Kelly!!
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This genuinely moved me, Anna. I’m so honored to work with you and be included in this incredible series you’ve created. Thank you! You didn’t miss a beat!
Love this series Anna- Kelly is incredibly creative and finds so many uses for every single piece.