Summer is finally here. It finally feels real. Although it has been hot as hell here, summer never officially starts for me until school is out and I am left to my own devices. At 26 weeks pregnant the heat is not my friend, but I’m making the most of it with low-key pool days, virgin drinks on a patio and time spent nesting (in the a/c), planning my registry and catching up with friends.

I also, fun-fun-fun, have time now to plan my summer trip with my Mum. I’m very excited. We used to travel together when I was in high school (Italy, France, and weekend getaways). This is our first mother-daughter trip in a decade. Being a real planner, I am eager to map out what to pack. Now the criteria is more stringent than ever – I can’t treat vacay as an extended photo shoot (like our trips to Santorini, Portugal and Spain). My growing waistline and easily-triggered emotions won’t stand for a suitcase that is packed to the gills, nor clothes that are cute, but uncomfortable. This isn’t usually an issue, since I’m pretty much comfort-before-style anyways.

Today: SHOES! 

Here are my top picks to travel with – for feet that will be comfy, well-supported and pregnancy-swollen (nice, right?). Let’s start with Soludos – whose shoes are cheeky, adorable and comfortable. They tend to be very classic, with on-trend details.

As we set out for our destination, the South of England, heading to boutique bed and breakfasts in the countryside, I am keeping in mind that we will not be walking more than I can handle at this stage of pregnancy…but I still want my feet to breathe, handle some serious walking up steps, to see ruins, farms, manor houses, and to handle old-timey streets. Plus, the footwear needs to be supportive and versatile enough to match all my outfits (stay tuned for Volume II).

Cole Haan has some wonderful options in driving shoes, loafers and sporty lace-ups. I went to the outlets at Niagara and found these for $50 less per pair than online/in regular stores, plus they offer a 15% off teacher discount (always pays to ask).

The court shoes I found are in a tan, super soft leather. While I love the idea of white runners, not so much in-love with them getting dirty. Bonus, the tan colour extends the leg line, rather than cutting you off at the ankle. To the right, the Weekender LX Loafer with Stitchlite fabric is breathable and featherweight, and the bottom left is a blush loafer with awesome sole cushioning that fits beautifully and is both lightweight and supportive. I went with the two on the left. All images: Cole Haan and available here.

The last great find, after lots of research, is feel-good company Toms (they donate a pair of shoes to someone in need for each pair purchased). My two faves for a summer getaway are the Honey Leather Camilia Sandal ($120), and the Navy Slub Chambray Clara Espadrille slides ($85). Signing up for a mailing list got me a %20 discount off my purchase and they have free shipping (though returns might prove costly). I have seen women schlepping around Toronto wearing the basic version of Toms shoes , or even wearing the lace version for weddings, so the comfort seems to speak for itself.

The Camilia has a bit of a heel, but not enough to mess with posture (left), the Clara (top right) is casual, but boho and cute/practical, while the lace slip-on is the often-chosen ‘fancy’ version of a Toms shoe (though I can’t vouch for the comfort of the lace on the skin after a day of walking). All images: Toms

I cannot wait to whittle this list down as I choose the clothes that will pair with them for my upcoming trip. I will never be a stilettos on the beach kind of woman, or on the cobblestones, or even (truthfully) from the taxi to the restaurant. But that doesn’t mean I don’t want to look adorable from head to toe.

What are your go-to shoes for vacations or long days out in your own hood, enjoying it like a tourist?