Reflections on Summer Dressing

I’ve spent the last few weeks desperately soaking up summer’s dimming rays as the transition to autumn encroaches, its chilly nights coming earlier and earlier. The shift to my cold-weather wardrobe is never a cut-and-dry process, usually unfolding slowly over the weeks of September and October. As I launder and fold away bits of summer clothes, sweaters crumbled in storage get shaken out and added to the shelf. It’s a gradual replacement.

The in-between period is always a good time to contemplate on the season past – the outfits I’ve been drawn to, the pieces I’ve lived in (or not), and the way my style has evolved. Personally, I love the mixture of analysis, sentimentality, and getting-a-little-too-cerebral-about-clothes spirit that accompanies these reflections. This post is an ode to the passing summer, with some lessons for the next one.

Some Outfits

These snapshots represent some of my favourite outfits of the summer. They reveal the variety in my summer wardrobe – a much more interesting palette of colours, prints, shapes, and textures than my winter greys and blacks. Yet, despite the range of styles, there are some clear patterns to how I dress, like my longtime summer uniform of a sleeveless top and a mid-length skirt. I’ve been wearing some variation of this combination for years, tracing back to a mint green polka-dotted skirt I thrifted in high school. Sometimes the skirt is swapped for a pair of sturdy shorts. On other days, I break the formula by opting for an easy tank dress. Topping off these base outfits, I usually throw on a lightweight button down, worn open or tied at the waist à la Daisy Duke. 

Although most of my days were spent working from home, I definitely felt more motivated to put on real clothes in comparison to last summer, when working in an old tank top and pyjama shorts was still a novelty (and honestly a survival tactic in that awful overheated apartment). As I revisit these looks, I can see that I’ve put more effort into how I dressed, even when I wasn’t going anywhere or seeing anyone. It’s been a summer of dressing my best, while still feeling comfortable, and letting my style preferences come through.

The Travel Capsule

Most of August was spent away from home on the Canadian east coast. Ever since I was a kid, I’ve always loved choosing and packing a travel wardrobe. It’s the ultimate capsule wardrobe exercise and it feels so gratifying when you get the combination just right. My approach is always to pack as light as possible; for three weeks I brought 4 bottoms, 5 tops, a dress, and a sweater (+ a rain jacket, a down vest, and a few pieces of sleeping/lounge attire). I made sure to bring clothing options for every weather scenario, although the sweater, rain jacket, and vest were ultimately unnecessary. The most-worn award goes to the brown skirt, which I donned a total of 10 times over our 22-day trip. I wore it everywhere: to the beach, to go sightseeing, and even to fish from a kayak. The two button down shirts were also incredibly versatile, so easy to throw on over a lightweight top or bathing suit. Although I certainly had enough to wear, I will admit I borrowed a flannel and oversized Radiohead t-shirt from my husband’s teenage Y2K closet during the trip. Overall, this capsule was one of the best I’ve ever put together — a wonderful balance of function and style with what felt like limitless outfit possibilities.

The Most Worn

My most worn items of the summer include old and new favourites alike:

  • The striped tank and black cropped t-shirt are two of the oldest pieces I own and are always summer go-to’s.
  • Purchased in 2018, the skirt with the abstract purple print was an impulse buy that I wasn’t convinced would stick around, yet it’s become a statement piece I wear all the time.
  • The navy silk skirt — the article that kicked off this blog — has become a foundational piece in my summer wardrobe, making every outfit feel effortlessly chic.
  • In a few short years, I went from avoiding button downs to being obsessed them. On any given summer day, I’ll have either the white semi-sheer shirt, the beige linen shirt, or the new striped shirt draped over my chair, if not my shoulders.
  • The black v-neck tee has been a great addition to my wardrobe; the cut is ultra-flattering, although I sometimes fear of flashing people.
  • While the beige chinos are a bit too warm for the thick of summer, they have been fantastic for cooler days and nights, as well as hikes through tick-territory.
  • The brown skirt has added a dash of vintage romance I didn’t know my closet needed. The skirt is so comfortable and I always feel great in it.

Thoughts and Reflections

In the past, I’ve struggled to find my footing with summer dressing, either getting too caught up in trends or falling into the trap of wearing boring basics. This year I think I’ve finally cracked the code. My summer wardrobe has a good variety of textures, colours, and prints, with a mix of structured, fitted pieces and loose, airy shapes. I feel inspired by the pieces I own, especially those that suit my style, while being practical and comfortable. Here are some other stray insights I’ve gleaned:

  • I love my silky summer tops (and do get decent wear out of them), but I wear my cotton machine-washable tops the most.
  • I tend to pair black, white, or cream coloured tops with mid-tone or colourful bottoms.
  • An item I don’t typically count as part of my regular wardrobe is my black merino bralette, but it was a staple this summer as a base layer.
  • I didn’t get a lot of wear out of my dresses this summer. As much I like my sleeveless summer dresses, most of them require seamless/nude underwear, which is not as convenient. Also, they’re not as fun to style as separates.
  • On the bottom, skirts are still my favourite, although my new linen shorts are getting better with every wear.

I won’t claim to be totally satisfied with my collection of summer clothes — because whenever I do, I seem to immediately reverse my tone by lusting after new things. Instead, I’ll discuss what I don’t need in my wardrobe.

  • Dainty summer tops: I have a lot of tops and it’s one of the easiest categories to add to when I thrift. Any tops I bring to my wardrobe in the future should be easy to care for (machine washable) and easy to wear (option to go braless).
  • Dresses: The data tells the story — I’ve only worn my 5 dresses a total of 10 times this summer. Eventually, I might replace one of my light-colour tank dresses with one in a pattern or different colour, but under no circumstances do I need any more dresses.

Over the past few months, I’ve learned a lot about my style preferences. As I look to the fall and winter, there are some changes I want to make to how I dress, although I plan to revamp my cold weather wardrobe gradually and intentionally. One of the key lessons I’ve learned is to not be stuck on achieving consistency and uniformity in my closet. I can have a functional, beautiful, cohesive, and small wardrobe without having to stick to one colour scheme or just a few “flattering” typologies. I’ve had a lot of fun getting dressed this summer and I can’t wait for the next one.

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