Welcome to sport mode

A perpetually overdressed person learns to love sportswear

Hello readers! This week, my friend Cait from the Overshare dropped a podcast episode featuring yours truly. In this conversation, we covered marketing, personal style, art, and body image - basically all of my personal and professional interests. Give it a listen and check out this companion article for all the links we mention!

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As a perpetually overdressed person, this summer’s real plot twist has involved bringing sporty elements into my outfits. By purchasing some casual accessories and pairing them with my polished summer staples, I’ve found a new way to dress that, for me, feels fresh and fun.

I’m not claiming to have broken any sort of mold, nor am I an expert in dressing this way, but I am excited, and I’m here to share my thoughts!

In this post, I’ll highlight the key pieces I’ve been wearing (and wishlisting), break down how I’m styling these items, and give some advice how to shop for and style sportswear.

Closet updates

While I’ve previously limited my sport-adjacent dressing to sneakers, this summer I’ve branched out a bit. Four new-in-my-closet items have launched what I’ve come to think of as my wardrobe’s “sport mode.”

1. Puffy bag, bungee strap, rope strap (not pictured) // 2. Camera bag // 3. Ugly chic sandals // 4. Ball cap (sold out)

1. A puffy crossbody bag from Topologie. This brand’s aesthetic is inspired by rock climbing. I held off on ordering online and visited the store in person when I was in New York City in June. The magic of this brand comes with the mix-and-match of it all. I picked a bag, crossbody strap, and a “just for looks” strap for a combination all my own. It’s beautiful, but it’s also functional: waterproof, lightweight, comfortable.

2. A camera bag from Movement. Yes, I bought another bag. This one is meant to carry an actual camera, but I loved the retro colorway so much that I grabbed it for daily life. With a spacious interior and two front pockets for my secrets, it’s quite useful.

3. A pair of ugly-chic sport sandals from Keen. I’ve finally succumbed to my months-long fascination with these hiking sandals. Before a recent trip to London in June, I bought a brown and pink style that served me well for the whole trip.

4. A sky-blue baseball cap. I’ve doubled down on my preoccupation with ball caps. Recently, I’ve been trying to wear them with regular outfits rather than just in a workout context. The key to buying the right hat, for me, is all in the fit. I’ve got a sizable noggin and ample hair. I like a style with an adjustable snap back, and I avoid anything that claims to have a “low profile.” Give me a lot of hat, and make sure it advertises the Toronto Blue Jays.

As is my tendency, finding things I like tends to lead me down an internet rabbit hole, looking for what other fun is out there. Here are four more things on my wish list! In this little roundup, I’m tentatively branching out beyond accessories.

1. Girly rain jacket // 2. Chonky sandals // 3. Sporty bag // 4. Green track pants (possible pipe dream)

1. A girly rain jacket from Hikerkind. I once read that any grown woman looking to be taken seriously should avoid bows. Needless to say, I now wear bows out of spite. I think this particular jacket would be nice on a casual walk, but I can also see wearing it to work in the fall and spring.

2. Chonky sandals from Teva. This is a bit of a cheat, because these sandals are already en route to my house. I love the unexpected color combination. Also, they’re meant for running so I expect them to be extra comfortable for daily life.

3. Sporty bag from Kavu. I will never stop buying fun little bags. I love the mesh upper and pop of orange.

4. Green adidas track pants. This is possibly a pipe dream for me. I’d like them to be the right color of green (I’ll know it when I see it) as well as short enough in the leg that I don’t have to get them hemmed.

Alright, back to what I already own. Since our purchases are only as good as what we do with them, allow me to show you some outfits!

The outfits

Something I enjoy about shopping is that new items help me see and appreciate my existing garments in a new way. The right purchases have the power to unlock a creative portal. I think this is what happened with sport mode.

In order to make my new sporty elements work and feel like “me,” I’ve been pairing them with my regular clothes. This is a very simple and probably obvious statement, but I have to say it for you and me: bringing in a new aesthetic (sporty) doesn’t mean your entire outfit has to fit into that aesthetic (sporty).

So, I’ve been wearing sport sandals with midi skirts, or a ball cap with blouses. The mix is important. The mix keeps things interesting. If I wear a ball cap with a t-shirt and denim shorts, for example, it runs the risk of feeling predictable. If I wear a ball cap with something that doesn’t normally go with a ball cap, that’s fun for me.

Here are four looks that I’ve been especially excited to wear:

Pairing sporty and dressy elements in this way is a true example of contrast dressing. I’ve long enjoyed the art of bringing in multiple, juxtaposed elements into a single outfit, but I’ve never been drawn to anything sporty because it never seemed like it was “for me.” Rather, I’ve tended to enjoy contrasting classic elements with playful elements, or masculine with feminine. I suppose this is the latest iteration of that pattern.

Just as an example, I wanted to show you what happens when I style my purchases more casually. I think the same vibe is there, but it’s more appropriate for going to the grocery store.

I have to say, I did love rolling up to the produce aisle like this. I felt chill but also, somehow, ready for anything.

Your turn

If you’d like to join me in infusing your everyday outfits with some sporty elements, here are some tips to make this happen while still staying true to your personal style. I’ve sorted my ideas into “tips for buying” and “tips for styling.” If you’ve already got what you need, feel free to skip this first section!

Tips for buying

• Consider what sport(s) you’d like to channel in your outfits, and even what sport(s) you’d prefer not to reference. You don’t have to play or even like a certain sport to borrow its style, but its shapes, colors, and fabrics should still speak to you or you’ll likely feel like you’re just wearing someone else’s clothes.

• Visiting a multi-sport department store, like Dick’s in the US or SportChek in Canada, can help you see a lot of options all at once. I secretly love that these stores are vast and dramatically understaffed because this means I can bring a bunch of clothes into the unsupervised changeroom and take way too long considering my options.

• If you don’t want to spend a fortune on a fashion experiment but you have a general idea of what you want, discount retailers are pretty handy. When I was looking for sport sandals, I found a lot of cool options at Nordstrom Rack and DSW, all at very tempting prices.

• If the shape or style of a piece is very outside your comfort zone, lean into familiar colors that you know will play well with other clothes in your wardrobe.

• Don’t settle when it comes to comfort. The entire point of sporty clothes is that they’ll allow you to move your body with ease. Being physically uncomfortable wearing a fashion experiment will only make you psychologically self conscious, too.

Tips for styling

• The easiest way to test out sport mode is to swap one element of a tried-and-true outfit for a sporty one. This way, you’re already mostly in your comfort zone and only one thing is out of the ordinary.

• You don’t have to pair your sporty element with dressy ones, like I have. The key, here, would be thinking of the most unexpected combinations.

• If you feel like a new sporty element is taking your outfit in a certain direction, name that direction and see if you can counter-balance it with other elements. For example, when I’m wearing something sporty it tends to be very casual, so I like to pile on a bunch of gold and silver jewelry to up the formality of the outfit.

• The mix-and-match of it all is inherently unserious. This is much more of a mental tip than anything, but if you feel like the outfit you’re trying out is a little strange, consider that it’s only strange because you haven’t worn it before. Making it familiar will take away the strangeness. Try wearing a new look out for a quick errand just to test it out in a low-stakes setting.

What next?

Moving into the fall and winter, I’m excited to see how my new items play with my cold-weather staples like denim jackets, wool mini skirts, and knee-high boots. I’ve come to understand that no pairings are off limits, and the weirder the combination, the more authentic it feels to me. Figuring out how the pieces fit together will be part of the fun!

As you can see with my wish list, I’m also interested in seeing how my recent love affair with sportswear can extend beyond accessories. What would a sporty top or bottom look like with my work-appropriate shoes or bags?

In any case, I think the lesson here is to stay open minded. If we find something appealing for any reason, even if it’s outside our comfort zone or what we’ve deemed to be our style, it’s worth pursuing it. Even if that just means trying it on. Life’s too short to box ourselves in. I hope you’ll join me in experimenting a bit!