I'm a Fashion Editor—Here's How I'm Wearing Boots This Fall

Welcome to Weekday Wardrobe, a series in which one Who What Wear editor or staffer will snap a pic of the outfits they wear from Monday to Friday. We'll break down where you can shop it all to inspire your own everyday style, no matter what's on your weekly agenda. 

Every time fall rolls around, I get inspired to break out my layers and embrace the new trends of the season but there's one piece that always gets me particularly excited: boots. Perhaps my favorite shoe style, I love when boot season returns. This fall, there are a number of cool boot trends that are emerging on the fashion scene and I decided to incorporate some of my favorites into my work looks this week.

Right now, my outfits are a balance of pieces that are comfortable but still polished (like relaxed trousers) as well as some eye-catching seasonal trends (like second-skin over-the-knee boots), and you'll find both of those in the mix. Here you'll spot some of the transitional looks I'm wearing for my workday, which all incorporate boots. From thigh-high leather boots to rubber Wellingtons to lace-up ankle boots, see how I'm wearing boots this fall.


I usually can't wait to wear a new piece when it shows up at my door and that's exactly what happened when these thigh-high boots arrived. So I put together this outfit starting with the boots specifically in mind.

It's been a while since I've embraced super tall boots, but that all changed when I spotted this sleek, second-skin boot trend all over the F/W 20 runways (more on that here). For my Monday look, I paired them with a padded tee and leather Bermuda shorts. I love the idea of styling them like leather leggings with the hem of the shorts covering the top of the boots. This is just the outfit to make me feel back to business on a Monday.


Loose, flowy dresses were one of the mainstays in my summer wardrobe. They're the perfect piece to wear working at home that feels equal parts comfortable and pulled together. This style from Merlette is one that I've been wearing on repeat.

Here, I swapped out my summer strappy sandals for a pair of knee-high rubber boots—another one of my favorite shoe trends for fall. I think the juxtaposition of the breezy dress with the utilitarian boots just works.

Today, I was getting ready for a Zoom meeting with our editorial team and slipped into one of my go-to outfit formulas these days: relaxed trousers and a padded tee. 

I'm a huge suiting person but I've been leaning more into loose-fitting styles that are comfortable but still polished. To bring this look into fall, I added these lace-up boots from Manu Atelier. They're one of my favorite pairs of boots from last year, but they continue to be hugely popular so they brought them back and you can still scoop them up.


Today, I put on this lace-trimmed slip dress with side cutouts for something pretty but comfy. While I would normally pair it with heels, I love the idea of toughening it up with a pair of rubber boots for something a little different.


If you know me, you'll know that I'm a big denim person, and I don't think there's a week that's gone by when I haven't slipped into a pair of jeans. It doesn't get more simple than wearing jeans with a tee, but I added a blazer and square-toe boots to dress it up a bit.

I'm all about balancing proportions, so opted for fitted straight-leg jeans with an oversize blazer. I think that the finished hem and the length of these jeans work perfectly with the ankle boots.


Bonus outfit! Even though you came here to see my weekday wardrobe looks, I also wanted to add in a weekend outfit that I snapped. Ribbed knits are one the fall clothing trends I'm most excited about and felt inspired to wear this dress with over-the-knee boots (yes, I'm looking for any excuse to wear them).