The 10 Styling Lessons I Learnt This Year That Have Upped My Outfit Game
And the takeaways you can apply to your own wardrobe...
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2024 marks some major milestones in life. My first full year on Substack! The year I finally worked out how to iron a shirt correctly! The year I started watching Real Housewives of Atlanta (and saw Countess Luann in concert!!)! It’s also the year where I really enjoyed getting dressed in a way that I previously hadn’t felt before. I’ve dug deeper, dissected, revised and become more in tune with my personal style. And as the year went on, I’ve been able to create a shorthand and ease that’s helped me get dressed every day in outfits I just bloomin’ love. Now, that’s a tricky thing to distil into ten digestible nuggets, but I’ve tried my best to deliver my hot-takes that you too, can apply to your own wardrobe…
Getting a colour analysis. Some people can get a bit sniffy about the whole colour analysis thing, but as someone who holds the holy trinity ‘Type A/Eldest Daughter/Virgo’ title, being given a set of rules as to what colours flatter you and which ones, well… don’t - that basically sounds like my idea of heaven. Of course, there are no rules in this style game, and it’s just a bit of fun, but the results of mine felt like a bit of gentle hand-holding as I dipped my toe into colour more than I have in previous years. A deep red, a muted olive, a rich earthy green - they’ve helped to add some variety to my mostly neutral wardrobe. You can read my full post on my experience here.
Re-incorporating animal print. I’ve loved animal print since my early twenties, but for some reason, a few years ago, I shed all and any leopard print from my wardrobe, leaving things looking a little light on ‘fun’. This year, I’ve slowly reincorporated it through a handful of purchases, both new and preloved, and I feel like my daily outfits have greatly benefited, not only from a pattern to break up the basics but also the texture to add some contrast to my look. You don’t need me to tell you that the Toteme Everyday Flats in Leopard Print* have been perhaps my best purchase of the year. If an outfit feels bland, they are a surefire way to make it feel more elevated. Plus, I’m able to wear them year-round (I’ll just pop a sheer sock on for the colder months). There’s a full animal print breakdown here if you’re looking to add some pattern to a sea of neutrals.
Expanding my shoe wardrobe. This is a BIG one for me. I’m always going on about ‘Having A Wardrobe For a Life We Have’, and in mulling this over, I realised that I needed more flat shoes that were comfortable enough for a 10k steps kind of day. But most importantly, I knew I didn’t want more trainers. I wanted something more structured to add polish and a classic feel to my look. So I worked on building a small shoe collection of flats that were uber comfortable but had the ability to shift a casual jeans and T-shirt outfit into something that felt smarter. Here’s what I settled on:
Black soft leather loafers with a slightly rounded square toe.
Chocolate suede loafers, because my outfit so often needs some extra texture to make it feel complete.
Toteme Everyday Flats in Leopard Print* - my Indyx app tells me I’ve worn them 44 times since I got them in May. There isn’t an outfit these shoes don’t go with.
Aeyde Uma Mary-Jane Ballet Flats* - a classic ballerina is too rounded for me, but these are nicely squared off and add a more feminine vibe to my look.
Defining my three words. Thanks to a session with the Queen of personal style herself - Allison Bornstein - not only did I settle on three style words this year, but I honed in on them. I created a recipe for myself that feels like a checklist that lives in my head that I can tick off as I get ready each morning:
Classic - I channel this through what is essentially a base outfit of basics. Think straight-leg jeans, T-shirts, cardigans and crew-neck jumpers. The top and bottom of my outfit usually fall into this category. Sometimes, I sprinkle in an element of tailoring with a shirt or a slim-line loafer.
Undone - I tend to add this in with non-clothing elements. So I usually leave my hair loose and air-dried or with a few tousled waves tonged in. I rarely wear my hair up unless it’s post-7 p.m., and I generally wear a little less makeup than I used to.
Polished - Jewellery has become a really important part of my look, and to me, it’s the single step that elevates very simple outfits into something a little bit special. I tend to gravitate towards something chunky, gold and oversized and my recent vintage Seiko watch ($100 from a jewellery shop in New York!), feels like it’s fast becoming part of my uniform.
Finding my seasonal uniforms. I started this style practice last year, but over 2024, I’ve done this experiment seasonally, and it’s been such a huge help in getting ready every day. If you missed the winter edition of my ‘Seven Uniforms’ post, you can find it here. But the premise was created by Liza, who cottoned on that the chicest people just switched between a small number of outfits all season long - hence the idea to create seven uniforms to repeat again and again until the weather changes and you need to regroup (you can read her original post here). I go one step further and categorise each outfit for occasions that crop up often. These days, I make six uniforms as I’ve edited my list to work for me and having a ready-made outfit for each of them means there’s always a backup on hand:
Childcare drop-off
Errands
Working-from-home
Working-from-home - filming day
Daytime work meetings & events
Weekend
Overwhelmed? Edit it down. Seeing as my physical wardrobe space grew this year, so did the amount, just a little. It goes with the territory, but being an avid declutterer I still like to feel streamlined. So whenever I’ve felt overwhelmed with that ‘I have no idea what to wear?’ feeling - I’ve gone back to basics. I truly believe that my Mallorca trip, where I packed just 10 items, created some of my favourite outfits from the year. I find packing a capsule of sorts makes sense for travel, but in terms of a home setting, I just use a seperate rail, or a section of my clothing rail to create a mini capsule for myself. I find it quite a calming practice actually, and I feel like it gets me working my style muscle again. A good one to try if you feel like your personal style stamina is lacking.
Developing my summer style. I have spent years being adamant that I hated summer style. I’d grumble all summer long and then breathe a sigh of relief when it was finally cool enough to wear a cashmere jumper, jeans and boots again. But this summer, I decided to put in a bit of work to find some practical solutions and you know what, NOW I MISS IT!! Looking back at photos just solidifies how much I really enjoyed putting outfits together over the summer months. Here are some key takeaways:
I tend to find myself wearing trousers most days, so instead of jeans I invested in linens and silks so I could still wear trousers, even on the hottest of days.
I always used to feel the need to wear bright colours, prints and florals - all of which I hate. Instead I stuck to my neutral palette, but added in more browns, creams and tans.
I lent more into the ‘undone’ element of my style - wearing woven leather bags, loose fabrics and beaded jewellery - it gave my summer looks a bit more personality.
Even though I don’t love dresses, I found a shape that worked for me - shift mini dresses. I loved wearing them with loafers for look that felt balanced.
Embracing bare skin. In 2024 I really tried to get a handle on my psoriasis. In recent years it’s worsened on my legs and made me feel self conscious to wear anything less than a pair of trousers. Hence why I usually boil all summer long. Thanks to good ol’ Vitamin D and a few shifts in my diet, over the summer months it was the best it’s looked in years and so I just got it out, and you know what? No one cared! And I wasn’t slowly perspiring away in a puddle of my own sweat in full-length trousers all summer long. HOORAY! And the options! Well, I wish I’d braved bare legs earlier, because being able to throw on a pair of shorts adds 50% more outfit formulas into the mix.
Establishing a working-from-home uniform. This is a more recent one, but just like my earlier point of realising that because of my lifestyle, it made more sense for me to expand my flat shoe collection, as someone who works from home at least three days a week, a working-from-home uniform would be helpful, too. I’d previously deemed jeans a solid choice for that, but as the weather has cooled slightly, I’ve craved cosier, more homey outfit vibes. And for me, nothing says that more than a matching set. So I’ve purchased a few and basically just cycle through them all week-long. Here’s my uniform:
A matching set, preferably an oversized top and a wide-leg trouser. Bonus points for being knitted.
A house shoe, basically a pair of almond-toe flats that I just wear around the house. It feels a little more elevated than a fluffy slipper and helps me to define my working-from-home uniform from my pyjamas.
Big gold jewellery. OF COURSE. Again it stops things getting too pyjama-y.
When it comes to leaving the house, I’ll wear it with a pair of loafers, or my Toteme Flats*, a big wool coat and a more structured bag to give some polish.
Working on my style. You know what? Sometimes it just takes time. I write a whole newsletter on personal style and I still have days when my outfit just isn’t it!!! But that’s part of the process and in general I do find that when I’m engaging with my wardrobe more, I feel far more connected with my style. Not only is that looking after it all physically: I make sure it’s organised, freshly steamed and ironed, fixed, repaired and ready to go. But I try to give myself a good 10 minutes each morning to style myself, so I have time to tweak and start from scratch if needs be. I reguarly scroll through Substack and Pinterest for inspiration photos and save them into seasonal folders on my phone. I log my outfits daily on Indyx which helps me to identify formulas I love and pieces that aren’t getting enough love. I put in the work and the more I do, the more get out of it.
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Until then,
Anna x
Thank you for compiling Anna! I cannot even begin to tell you how much the “comfortable shoe that is not a trainer” has changed my life. As a gal living in hilly San Francisco I thought I **needed** fun sneakers but your POV on this has really shifted my mindset!
I love your style and your style musings Anna, by far my favourite style content online! Thank you for all the great ideas, thoughts and learnings you’ve shared with us in 2024!