POV: You Booked A Session With Your Favourite Stylist

...and it's the best wardrobe investment you've ever made

Yesterday, I had a personal styling FaceTime session with the one and only Allison Bornstein (who is now on Substack!!!). It’s my third time doing it, and I can hand on my heart that it’s the best wardrobe investment I make. In just one hour, she works her magic, conjures up 17 new outfits, imparts her styling advice, and I’m left feeling very excited about what’s in my wardrobe. I’ve documented my past sessions here and here and always point to those as a pivotal moment in my style journey. From our first session onwards, my daily outfits got a whole lot better, and I felt everything style-wise slot into place in a way that I hadn’t experienced before. Just two hours with Allison changed the game. Here’s why I’ve found it so helpful:

• She’s helped me pin down my three words—‘undone’, ‘classic’, and ‘polished’—which I genuinely think about every day when I’m getting ready. Of course, those terms have flex and ease built into them, but they are always a great starting point for me. When we first met, Ralph was one, and I was still at the beginning of my ‘WHAT THE HELL DO I WEAR NOW?’ postpartum journey. I really feel like my first session with her helped me navigate that new chapter.

• Her wise words and style advice will make you fall in love with your wardrobe again. Although she does offer a shopping recommendations package, you can opt for just the one-hour video call, and she’ll work with what you already have. I love that. How great to end a session without a shopping list but instead with a list of brand-new outfits that you can wear RIGHT NOW.

• It’s ultimately just very fun. I wouldn’t say I’m someone who loves a video call, but the whole thing is very chill, and Allison is so warm; she’s the kind of person you feel like you’ve known for years. Be prepared for the hour to fly by.

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Having done this video call styling set-up a few times now, I find these prep steps helpful:

1. You’re about to try on a load of clothes, so I took a quick shower before, skipped my usual body oiling step, and went sans makeup, too. It just meant I wasn’t worried about making all my collars orange.

2. Nude underwear is a must!!

3. Organise your set-up so the stylist can see as much of your wardrobe as possible, and you are in front of a mirror.

4. Answer the call on your laptop so you have your phone free to take photos (and make sure everything is charged up or plugged in!).

5. Have a big drink nearby - you’re about to be yapping a lot.

6. Ensure your wardrobe is tidy and that all of your favourite pieces are out of the wash—you want to make sure all your best bits are on hand.

7. Come to the session with a question to solve or some specific pieces you’d like help with.

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This time around, I went to Allison with a summer styling conundrum. Although calendar-wise, we’re in the final part of summer, it feels like the hot weather has only just got started in the U.K, and I’m getting bored of my usual summer pieces I’ve had on rotation - just give me autumn already! So, I wanted Allison’s help in creating some fresh summer ideas and a few ones that will see me into the cooler weather, too. And, of course - as always! - she delivered.

Here’s how it went outfit by outfit…

This is where we started. She asked if there was a summer piece I’d worn a lot already, and my answer was these Toteme trousers*. Then I showed her a few of my tops and she picked up this one for some added texture. Instead of going tonal, we added contrasting shoes and a bag.

Allison spotted these snake print ballerinas* in my wardrobe (her eyesight is NEXT LEVEL!), so we gave those a go and added a smaller black bag. I always think of wearing these trousers with an open-toe shoe, but I loved them with these square-toe flats. Food for thought to experiment with my shoes more!

To transition it into autumn, Allison added a trench and the suggestion to wear a long-sleeve knit underneath it for extra warmth. One of those occassions where it wasn't 100% necessary to try it on, but I grabbed a photo for future reference.

Using the same trousers and shoes, Allison wanted to see it with just a vest top* on top. My gut would have done this outfit with a flip-flop and a straw bag, but there’s a bit of Allison’s ‘Wrong Shoe Theory’ and a bit of ‘Wrong Bag Theory' going on here, too. It feels much more polished with the big leather tote.

Same base, but we switched the shoes for my Emme Parsons ones*, added my Dragon Diffusion bag* and a shirt over the top. Loved the outfit, but I’m realising that the shirt isn’t my favourite - the drop sleeves add too much volume around my upper arm. I feel like this Sézane one* might be a better fit. I’m eyeing it up.

To take the trousers into an autumn look, we added this FAB suede jacket* that was VERY Allison-approved and a black bag and shoes. I feel I always have a tendency to pair new colours in my wardrobe with black, and actually, as Allison explained, black can feel quite heavy and make the colour feel too stark. Here with the cream, it blends more cohesively.

Two ways to wear it when it gets cooler; with white wide-leg white jeans and with light-wash blue jeans - both with brown or black boots and a bag. I can't wait to wear these two outfits!

Then we moved on to another summer favourite - I love that Allison’s prompt is always ‘What are YOU loving wearing right now?’. It just means that the end result is something that I’ll actually wear. So we played around with this shift dress*. LOVED it with the Mary-Janes*.

Just a switch around of the bag, which we both agreed felt bery Jane Birken and I’m here for it!! I feel like this could be a great London meeting day outfit.

Two different layering options over the top for chiller days; I liked the denim shirt (and I think I would have liked it even better if it was buttoned up - I'll have to experiment!), but the suede? ADORE.

A slighter sleeker option with the slip-on flats and my snake print bag. I feel like I neglect this bag during the summer, so this was a good reminder to dust it off!

Then for more autumn looks, Allison suggested throwing a trench over the top, which is something I always SEE in photos, but is something I never really do. I just needed a bit of hand holding, because I love this long coat, legs out combo.

Then to finish it off, Allison wanted me to try on my white shift dress* with a white shirt over the top for some extra layering. I loved the strap sandal with this and it felt like an easy, but still polished weekend outfit for me.

So there you have it. One hour, 17 outfits and an excitement in my belly for summer dressing again. Allison, you are just WONDERFUL and it’s a wardrobe investment that I’d recommend over all others. A way to invigorate things, hone your personal style, create a tonne of new outfits without even having to buy a thing. I’ve already booked in my next session!! Like what you see round here? I’m always yapping about all things personal style and would LOVE to join you in your inbox…

Anna x