I Booked Five Hours of Personal Styling Sessions & Here’s What I Learnt
...and it's not what you would think.
The highlight of SHOP YOUR WARDROBE month for me were my five styling sessions. Could you tell? Throughout January, I spent a lot of time in my wardrobe under the supervision of five extremely talented Personal Stylists who are the best of the best in their field. After each one, I debriefed with you on my key takeaways, all the outfits we created and the lessons I’d be applying going forward.
My reason for doing it wasn’t because I was in a particularly bad place with my style; like most things, it’s better to ask for help when you’re a little dissatisfied, rather than waiting to hit rock bottom. But I create content online, and it made for a great series! I got to connect with women I admire in the industry and be a student for once. I live for this shit! I’d done a handful of sessions with Allison Bornstein before, so I knew it would be FUN!!! I was really looking forward to it and loved every minute. But what did I learn?
I thought this post would be one long list of the styling tips that I’ve applied since our sessions, and although there are definitely concepts I’ve found myself thinking about or tweaks I’ve found myself doing when I’m getting ready, I’ve learnt more than that. It feels like there’s been a bigger shift that has happened. I have a better understanding of how my wardrobe works for me, a more concrete idea of how I want to build on that going forward, and it’s made me a better buyer?! Discernment levels off the chart!
Before we crack on with my thoughts, here’s a directory of all the posts I created and a little bio for each Stylist:
Anna Baldwin - read about our session here. Best for: you’re feeling settled in your wardrobe, but want to add a little funk, colour, or decode Tibi styling concepts.
Reva Luft - read about our session here. Best for: you’re a busy Mum who is trying to juggle the school run, whilst still feeling effortless and chic.
Kelly Klein - read about our session here. Best for: you want to learn those little tweaks that can make your wardrobe feel brand new.
Angie Uh - read about our session here. Best for: finding new ways to style older items or starting from scratch, that’s her speciality.
Allison Bornstein - read about our session here. Best for: you’ve never done a styling session before - she’s the OG who's going to put you instantly at ease.
Firstly, the biggest impact was that it gave me the confidence to get rid of A LOT of items. I did a big cull that I documented last summer, where I had the realisation that in order to do this in a way that actually works, you have to physically try every single item on your body. Boring, but effective. This time round, I didn’t tackle my wardrobe in one fell swoop, but I did little and often, targeting pieces I knew, in my heart of hearts, just weren’t working for me. Did I actually want to wear it? Or did I buy it just because I felt like I should wear more colour? Or deviate from jeans more often? Do I want to do that? Or am I quite happy wearing what I want to wear? It’s as simple as that.
Over these sessions, I realised that if I’m constantly trying to find ways to style ‘problem pieces’, then maybe they just aren’t meant to be hanging in my wardrobe? The real answer is that there’s probably a 50:50 split in that equation. The breakthrough I had with my By Malene Birger Jacket in my session with Reva meant it’s morphed into a piece I’ve worn more than a handful of times since we rebranded it as a cardigan to wear around the house, rather than just being a jacket that’s saved for spring. The same with the plethora of outfits Angie created with my brown-y purple vintage Levi’s. But my Apiece Apart Burgundy Cords, which have taken up so much time and space in styling sessions over the years, were never a pair of trousers I found myself wearing regularly, let alone once or twice a year, despite all the problem-solving. They were taking up time (and space!) that could have been more effectively used elsewhere.
The obvious category of clothing that I’ve removed from my wardrobe is items that didn’t fit. This clicked during my session with Angie, when she asked why I rely on white trousers so often in the summer months but never in the winter. The truth was that neither of my white denim options fit me, but I was holding onto them just to ‘fill the category’. One pair were too tight on the thighs, the others too big and with hems that dragged on the floor - not what you need when it’s pouring down outside. I didn’t want to waste my money rebuying a category I already thought I had covered, but both pairs just sat in my wardrobe and because neither fit, I was lacking the opportunity to add range to my everyday uniform.
Now, this totally wasn’t the point - it was part of my SHOP YOUR WARDROBE series after all!! - but I did end up buying a few items. I wasn’t pushed by any of the Stylists I worked with to do this (although Reva did point out a few gaps), but through spending literally hours playing in my wardrobe, I could see that there were perhaps a handful of pieces that could be useful. Whereas before I felt like every item needed to push me or extend my wardrobe in a way, I focused more on real-life everyday purchases:
A turtleneck* to replace my tired UNIQLO one that I’d had for 10 years and always felt a little sheer (I’ve still kept that one to wear as more of a base layer).
White jeans that actually fit me* (I’ve also got Chloë from Pin Denim on the hunt to find me a vintage pair!).
A grey sweater* instead of a knit, to add a more relaxed edge to outfits, seeing as I wear my grey cashmere knits so often.
Proper waterproof rainboots* that I didn’t think were super ugly.
I may have bought things, but I’ve also been far more ruthless with returns. I’ll admit that sometimes I just can’t be arsed with a return, or the back-and-forth required when you’re not 100% sure that something isn’t right. But the UPS parcel guys and I have become tight because I’ve been committed to the faff. Take my search for a grey jumper as an example. First, I tried The Great College Sweatshirt*, but it was too scratchy; this DONNI one* felt too much with the delivery and duties I’d have to pay; I didn’t like the cool tones of the Still Here Sweatshirt* and when I first tried the MOTHER The Biggie Jumper* in a medium, I wasn’t sure if the arms were too short. So I ordered the large, but when I tried it on, it completely lost its shape around the body. It turns out I liked the shorter arm of the medium - it made it easier to pull the sleeve up a little, which is how I like to wear it. So yes, a FAFF, but I know I got the right one for me.
I think it’s an OG Allison Bornstein idea, that I also spoke about with Reva, but the whole ‘try three outfits on, when you buy something new’ is a concept to live by when new pieces are auditioning for a spot in your wardrobe. I used to just purely focus on fit. As long as it ticked that box, then I welcomed it in with open arms. But whether a piece actually works in your wardrobe is so much more than that. PLAY! It’s fun! And it’s going to dramatically reduce the incidences of ‘problem pieces’ in your wardrobe, because you’ll be able to spot them immediately, before you’ve pulled off the tags this time. I totally understand some of us might fancy having those things that really just work in one scenario, and there will be exceptions to this rule - I’m thinking of a Faithfull Polka Dot Maxi Dress I own that has ‘wedding guest’ wrriten all over it - but I think for the most part, and for me personally, this litmus test is going to help my wardrobe feel more cohesive and workable as a whole.
I wanted these sessions to have realistic applications for my everyday wardrobe. That polished ‘meeting day’-mode is something I quite enjoy creating and find relatively easy (and realistically is a mode I need to switch to on a once-a-week basis at most!). So with these five sessions, I made sure that I briefed each Stylist on my daily reality - working from home, chill weekend plans with the family and doing drop-offs and pick-ups. It meant we focused on true everyday dressing for me. It gave me a renewed focus on functionality, and I’m finding myself paying more attention to my base outfit, rather than rushing past that step just to get to the accessories. Heck, even a tote and rainboots can look chic with the right crewneck, your favourite jeans, and a longline blazer coat!! It’s less about the seasoning and more about my base outfit, and I think I’d lost sight of that.
I thought looking elevated was at the top of my hierarchy of style needs, but really, it’s a function. My bag needs to fit everything, my shoes need to be comfortable, I need to be warm, but able to remove layers when I get too hot. I don’t want to be fussing, nor overthinking it. Just wear the darn clothes! Give it a go! Feel that energy in the session I had with Allison! I think I’d got too caught up with every outfit being ‘just’ right and focusing more on the overall look, rather than how I felt in it. But sometimes you have to mess around a little, try something new, note when it works and accept and pivot when it doesn’t. It’s not that deep.
All of this isn’t to say there weren’t specific, more quantifiable changes I’ve shifted in my wardrobe since. Namely:
Grounding an outfit with black, as discussed with Allison. I think I’d become a little fearful of black, but it still has a place in my wardrobe, especially if I use a light touch. Like a black bag, or jumper around the shoulders, or black sunglasses, to give the outfit some punch.
Making sure my socks are tonal with either my trousers or my shoes - again, an Allison tip. Looking down whilst writing this, I’m wearing my black sheer socks with my black leather loafers. WIN!
Sometimes it’s just tricky to know where to start. Both Kelly and Reva suggested starting with shoes (and, in the colder months, your coat, too). Function is then automatically baked into your outfit.
Every single Stylist I worked with suggested that my statement coats are my real ‘wow’ pieces, and to lean on them to jazz up a simple jeans-and-tee.
Another thing everyone picked up on: I love a long line in my outfits. So jeans, a T-shirt, and a longline coat make a solid outfit for me.
Kelly’s tweaks are all in my daily rotation - the cuff pull to add extra detail, the way she suggested tying a jumper around the shoulders, how she tied a shirt around the waist and cuffing jeans (I’ve got mine cuffed today!), are all things I’ve played with since our session.
Rebranding items is often the way to solve ‘problem pieces’, which is something I’ve done with Allison before. Reva did it with my By Malene Birger Jacket, and Anna suggested using my jackets as tops, which is something I’m looking forward to doing once the weather warms up.
It might be an extremely boring item, but I think a grey jersey jumper* is about to be an integral piece in my wardrobe. As Allison said, it’s a good way to dress an outfit down. Angie worked a lot with grey jumpers to get my brown vintage Levi’s to work for me, and Reva reckoned it was the key to me unlocking a lot more outfit combinations.
I thought I’d end up with a shedload of outfit formulas to fall back on when I was feeling stuck (and I did!) and small, but mighty styling adjustments to have in my back pocket (again - I do!). But the unexpected change for me is how it’s led me to streamline and refine my wardrobe to a place where I feel like it’s precious real estate. Everything that remains feels like it’s earned its place, and anything new coming in really has to prove its worth. I’ve never had that feeling as strongly before. I have a renewed understanding of my lifestyle and the style needs within it. I need a little more rainboot and a little less ‘pointy toe heeled boot’, and that’s ok!! I feel like I’ve got the tools I need to make those adjustments in a way that feels the most ‘me’.
I know this is all starting to sound a bit like I’ve reached some elusive wardrobe nirvana, but it’s more just a feeling of comfort. Like it’s got my back, you know? Even if a day requires a hoodie and sweats. I’m prepared!!! It’s just that I have clarity right now. I just needed five hours with five very talented Stylists to achieve that…
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Anna welcome to the gray sweatshirt club! I own 7 and they all do different things and yes I know that’s a lot and no I will not be taking further questions at this time 🤣
Tiny point that I seem to have raised with several people already (!) — when, exactly, did a sweatshirt become a (jersey) jumper?!! ENTIRELY different beasts!