Styling from the Ground Up, A Lesson Learned from My Rail This Week
You see, certain shoes, like the chunky lug sole boots ideal for chilly, rainy weather, are better suited for specific conditions. So, instead of my usual method of choosing shoes based on whim, I decided to let my boots take the lead. This meant reconsidering some of my clothing choices to complement the boots I knew I’d need to wear.
Take, for example, the barrel jeans I had initially chosen to style for the week. Normally, I’d opt for sneakers, mules, or lighter footwear to match them – not lug-sole boots. However, given the cold and rainy conditions, this wouldn’t suffice. With the lug sole boots as my starting point, I swapped out the barrel jeans for a pair of straight-leg crop pair of jeans – which you will see styled below – and suddenly, the outfits started to fall into place for the week.
So, if you find yourself puzzled or in a rut while putting together outfits, try flipping your usual process on its head and start with your shoes. You might just uncover new ways to style your clothes and gain a fresh perspective on your wardrobe.
I haven’t worn this Cashmere tank dress much, despite wearing it frequently over the past two weeks. Styled with my Figue Logan Overcoat, lug sole booties, and Think Royln Elton Hobo bag for a casual look.
From the archives: cashmere tank dress styled with the Veronica Beard Dickey Blazer (shown here with dickey zipped out), and option with a wrap sweater, giving the look of a skirt, but the ease of a dress.
As mentioned in last week’s video, I love this Vince suede jacket but really don’t wear it much, in part because I am afraid I will stain it or get a watermark on it. But clothes are meant to be worn, and this jacket is super versatile for day or night, I love the color and styling, and she adds some life and color to my black foundation pieces like my cashmere sweater dress (again!) and Frame Jetset wide leg jeans
First off, take note of the gold chain strap on my Rebecca Minkoff handbag – this came off of the Think Royln Elton bag that I am wearing above. That’s right, my Elton Hobo bag came with 3 straps! The Logan Overcoat made a comeback, this time complemented by Hue Faux leather joggers (now on sale!) and a JCrew crop cashmere turtleneck in winter white. However, the overcoat vibe wasn’t resonating with me for a dinner date with Mr. Bell. So, at the last moment, I opted for my reliable Veronica Beard Dickey jacket in camel. Which ensemble do you prefer? Oh, and I love these mules…Anine Bing “Zoe”, discovered on my last trip to NYC. similar style for less, here, here
No round-up would be complete without a few more ways I style my Vuori Joggers, Jenni Kayne Mules, and Athleta longline quilted vest!
Once I realized that styling my closet for this rainy week needed to start with my lug sole boots, I switched out the Barrel jeans on my rail for my trusty straight-leg crop jeans from Mother, and the outfits came together. You see, the barrel jeans – which I will style in a future post – do not work well (on me) with heavy boots as I feel it adds more weight and clunkiness than I am comfortable with, to my bottom half. These jeans have a wider leg opening which allows them to sit right over my chunky boots in a manner that works for me. Styling problem solved!
5 Things I Learned This Week
- When shopping online, especially with final sale items, do a reality check with your closet to see if it works with items you already own.
- When your outfits may be limited due to weather, consider styling from your shoes up
- Even the best-planned outfit, may not vibe with your mood when you go to get dressed. Be flexible and open to switching pieces up.
- What pieces in your wardrobe, like my Elton Hobo, can be styled/worn in ways different than intended?
- Black is always a great choice when it comes to purchasing investment pieces for my wardrobe. What base color is best for building your wardrobe?
Exact or similar items from this week’s Rail
This series is all about shopping mindfully. Enjoy checking out what other style bloggers have in their closets, but remember, these suggestions are just for convenience and inspiration. No need to rush out and replace what you already have—take a look in your closet first before considering new buys! Shoes and Accessories:About The Series
Every other Monday, I’ll share the second part of this series, offering you a peek into what I’ve been wearing off my Rail. Expect some insights, reflections, and maybe even a few style tips to spice up your wardrobe adventures.
Curious about what inspired this series? PRESS HERE to check out my post, Buy Less, Wear More in 2024.


I have Chelsea lug boots and they are great for rain ! Boots first makes sense and is sensible. I liked that idea. Thx
A pair of waterproof Chelsea lug boots are on my list for Fall 2024. I managed to get by with the Tory Burch lace up boots this season, but they are heavy and not as versatile. I think I would get a ton of use, for many occasions out of a simple pair of Chelseas like yours.xx
Hi – I live in the North of England and the weather from October to April is generally cold and frequently wet, foot wear is almost always my first consideration, followed by outerwear, layers are essential here and I love a great crossbody bag to pull my look together. I’m really enjoying this series it’s definitely helping me to focus on what I have rather than dashing out to buy more. I’ve started to shorten some of my wider legged trousers to allow me to wear them with trainers (sneakers) rather than heels which had opened up a whole lot of new options. Looking forward to your next update. Thank you and very best wishes Tina
Hello Tina! North England, wow, now that’s some real weather up there, I bet you are a pro at layering and what to wear in the cold wet weather! Honestly, I have never had to consider footwear – or outerwear – in the past, as our weather is usually so mild. I like how you use a crossbody bag to pull your look together. I also love to hear how you are hemming your wide-leg trousers so that they work better with your trainers – since that is what you wear on the daily. Brilliant!
Thank you for joining the conversation with these very helpful tips and happy to hear you are enjoying this new series as it has helped me to shop my closet more intentionally as well. My next video is a 2-fer, what I wore for the week along with how I packed my carry-on for a week of outfits in New Orleans, Louisiana! xx Suzanne