067. Seven-Look Season: Sharing My Summer Outfits
And How I Recently Recalibrated My Personal Style
In a Q&A late last summer, someone asked me, ‘What Outfit Made You The Happiest When You Wore It’? It stuck with me for weeks and got me spiralling. I had just pulled the plug on the size-inclusive brand I spent four years building, and my brain could only think of clothes in terms of how they fit and flatter the body. I had been obsessing about how clothes looked for so long that I forgot to consider how they made me feel. I scrolled past the dozen pastel, floral, form-fitting dresses on my recent camera roll and landed on a printed T-shirt and linen knee-length shorts outfit. That 12-year-old boy get-up is what made me the happiest that summer.
Recalibrating
My perspective has shifted in the last year, and the way I dress evolved as a result. Silhouettes still matter - I’ve become even more fit-conscious - but I no longer dress for my body type. Not because I am rejecting that concept; it just so happens that I felt rubbish in those clothes. I had a lot of internalised ideas to break down. It still feels weird to button a shirt all the way up or to put a dress that perfectly contoured my curves in the donation pile. I have replaced tight fits with structured ones. I dress a lot more androgynous than I did a year ago. Something I feel pulled to lean into more and more. In sophisticated and feminine dresses, I felt constrained and flustered. In the new outfits, I feel limber and more audacious. I wear more oversized and boxy silhouettes than ever before, and, most surprisingly, I like how I look in pictures for the first time.
If you’re a visual person or you like frameworks, I’ve written about discovering your unique sartorial identity here and here. However, not everyone needs moodboarding or personal styling sessions. What most helped me was tuning in to how I felt in the clothes I put on my back. That and getting colour analysed. It’s very unpopular right now, but it changed the game for me.
Choosing Outfits
The outfits in today’s letter are from a wardrobe in transition. When I put together what I would wear this season, the challenge was picking the most versatile pieces from last summer (e.g. the Dries top or the vintage maxi skirt) and styling them with the newer pieces. I purchase around twenty new pieces each year - a ballpark, not a rule - so dressing will feel like this for a while. Trying to buy a brand new wardrobe in one go would inevitably lead to some buyer’s regret. The outfits that mix old and new - e.g. Ulla Johnson blouse (old) + Loewe shorts (new) + vintage Gucci tote (old) + Jamie Haller sandals (new) - turned out to be my favourites.
Note that if you are in an exploration phase, separates are more versatile and, therefore, have more longevity. There’s only so much that can be done to recalibrate the style of a dress. Tops and bottoms can survive many wardrobe rehauls, and in doubt, they might be the wiser purchase.
I attribute being able to make these outfits work to the planning session I had at the start of the season. If you’re new to the newsletter, I have long ago adopted a framework for wearing a small number of outfits on repeat. After some trial and error, I found that the number of outfits I need to suit my lifestyle - mid-thirties,