The Workhorse & The Showpony: Lindsay Sword

How this merchant mom of three and Substack fave approaches her wardrobe!

Feb 01, 2025

Hello and happy February! I don’t know about you all but I am really happy to see the back of January - it’s always suuuuuuuch a rough month…this year in particular for TOO many reasons I won’t get into bc: depressing! But onward we march, hopeful for brighter days ahead.

I’m kicking off the month with the fourth installment of this series, which is all about exploring the duality of our wardrobes. (Read one, two and three here!) This time, I’m thrilled to feature one of Substack’s very own faves (and certainly mine)—the talented Lindsay Sword!

For those of you who don’t know Lindsay, you’re in for a treat. She’s a friendly, fabulous and fun 39 year-old merchant and mom of three boys, who splits her time between NYC and Wyoming. I discovered her SS several months ago, when she wrote about the rise of barrel jeans and their roots in cowboy culture—just as the “Cowboy Cousin” micro-trend was popping off. As a self-proclaimed barrel jeans obsessive, this post was music to my ears. Lindsay’s content always feels fun, relevant, and thought-provoking—but very relatable, which is ultimately what makes her, and her style, so intriguing to read about!

Lindsay is also someone who truly exemplifies the duality of getting dressed, and how we can lean into different aspects of our closets to create different looks, ideas and feelings. In fact it was her post, Curate Your Closet (Like It’s The World’s Best Store), that prompted me to reach out to her for this series, as she hit on so many incredible concepts that we touch upon here, too. Her genius product pyramid of Evergreens, Seasonal Keys and Heavy Hitters is, in essence, a more in-depth take on the Workhorses and Showponies. Ultimately, we’re both looking at how different categories of pieces in our closets interplay with one another and enable us to express ourselves authentically.

Let’s dive in with Lindsay- you’re going to love this glimpse into her wardrobe go-tos!

About Lindsay

What are your three style words? Preppy, Eclectic and Casual.
How do you decide what to wear every morning? I usually plan it during my run or while in the shower. If I’m traveling, I plan outfits in the Notes app. I’m a word person and need to type my thoughts out (aka a writer lol). I also add in reference photos to remember a color combo, layering moment, or style trick I want to emulate.
Do you find getting dressed enjoyable or a chore? Enjoyable, when I have the time! A chore, when I don’t. And with 3 little boys, it’s often the latter! One goal of mine in 2025 is to do more outfit planning. (I’m awful at meal planning, but maybe I can do this!) There’s so much inspiration and advice on Substack to help with this, I’m feeling motivated.
What’s your favorite thing about fashion? Least favorite thing? My favorite thing is how we can experience art and creativity daily through fashion. Least favorite is the environmental impact and waste, hands down.
Your fashion life motto? Fashion should feel good, physically, mentally, emotionally. Life is short, wear what makes you happy. (AMEN Lindsay!!!)
What do you prefer in your wardrobe, a workhorse or a showpony? Probably a showpony :) I can’t help it! I love fashion, I work in the industry, and for as long as I can remember, I’ve just been enamored with great clothing. I love looking at it, reading about it, shopping for it, styling it, wearing it. Beautiful fabrics, fun colors, great patterns, and intriguing shapes all bring joy to my life every day. What a gift!
What role do you think each type plays in your wardrobe? I definitely need both in my wardrobe, because workhorses make the showponies shine. You can’t make an outfit entirely out of showponies (or at least I can’t, because one of my style words is ‘casual’ so I feel uncomfortable when I’m too dressed). The endless combinations are what makes the fashion puzzle so fun!
If someone on the street gave you $1000 and told you it could only be spent on fashion, would you buy a workhorse or a showpony and why? This is SUCH a fun question. I will admit I’m not much of a planner, and I tend to shop by feeling. But if someone gave me $1000 I might buy this Dries Van Noten blazer…I love it so much but it is such a showpony and SO pricey. The $1000 still wouldn’t even cover half of it, even on sale. Dries is my favorite designer; I’ve been saving up and splurging on pieces of his since I got my first job. (I’m so sad he’s retired but feel hopeful that he’s passed the reigns to someone on his team.) I love the menswear checked wool combined with those over-the-top embellished sleeves. I feel like this ONE blazer sums up my personal style in one piece. It’s so good. 100% a showpony.
Anything else to add? I’m such a fan of yours, Sogole! You inspire me every week, and your words and style always spark something in my brain! Thank you for inviting my to think more about my style, I loved doing this! (Blushing over here, thank you!! Right back at ‘ya!)

The Workhorse

I just love the many creative ways Lindsay styles her workhorse! **TOP LEFT:** old Theory wool blazer, same throughout (similar), Ganni striped tee (similar and an RL option) Frame jeans, Loewe boots (almost sold out so try this or this) **TOP RIGHT**: Everlane tank, Everlane jeans, COS flats **BOTTOM LEFT:** old Veronica Beard top (alt, alt), Everlane jeans, Dries Van Noten boots (limited sizes, another great option) **BOTTOM RIGHT**: Rhode dress (RIP!) similar but almost sold out, this looks fab too! same Loewe boots as before (she knows how to put her workhorses to work!)

What is your go-to workhorse item in your closet? I’ve had a black Theory blazer for almost twenty years that is the definition of a workhorse piece. (In fact, I’m wearing it in my Substack profile pic!) It’s so old, it was Made in the USA…I actually think I replaced it once at a Theory outlet (maybe ten years ago?), but for all intents and purposes, it’s been the item that’s lived in my closet the longest.
Why is this such a workhorse piece for you and your lifestyle? It’s actually a little surprising because I’ve never worked a corporate job with a traditional business dress code (A&F preferred us to wear their hoodies and jeans shorts to work!) I don’t wear a lot of black otherwise (I can never figure out how to wear black pants), but this single blazer has been the most useful piece in my wardrobe and also makes me feel really good when I wear it: sharp, smart, and dare I say even a little sexy?? To be fair, I’ve always thought blazers were a little sexy, although I’m not sure my high school boyfriend would agree (luckily he’s now my husband, so the blazers must have worked a little bit!)
What do you look for in a workhorse? It must be made from high quality materials (meaning natural fibers like wool, cotton, linen, cashmere, leather, etc.) and should be versatile in terms of dress code, seasonality, and style.
How do you generally style this piece? 95% with jeans, 5% with a midi skirt or dress. 95% of the time with jeans, since a blazer and jeans is the #1 outfit in my book. Always hits, never misses. 4% of the time I style it with a midi skirt and boots or loafers and 1% of the time I’ll wear with a maxi dress. (I almost never wear dresses.)
Was it a splurge or a save? At the time, it was a splurge even though I’m pretty sure I got the original and the replacement at the Theory outlet. I did just splurge on this on sale - yes, still a splurge despite being on super sale. It’s my first piece from The Row, and while I have loved my Theory blazer for two decades, I needed to refresh the shape and fit towards something a bit more modern - a straighter cut and bracelet sleeves. I think it will be my new workhorse and hopefully will accompany me through the next twenty years, or more!

If you happen to be in the market for a black blazer (am I ever not in the market for one?!), here are some solid options at diff price points, each with a slight twist!

as workhorse as it gets! one, two, three, four (almost all on sale!)

The Showpony

The coolest cowgirl around! Sold out Valentino boots (comps below), &Daughter sweater (on sale! also in brown), Andersons belt, Agolde jeans

What is the go-to showpony piece in your closet; an item that feels particularly unique or special? I recently bought a pair of Valentino cowboy boots with floral appliques twisting all over them. They’re wild, and I’m in love. Every time I wear them, people comment on them. I love how eye-catching they are, and that they seem to make people smile. They definitely make me smile, which spoiler alert for the next question, is all I look for in a showpony piece.
What do you look for in a Showpony piece? That it makes me SMILE.
How do you usually style this piece? With jeans, obvi! (I’m sorry, I’m boring, but they’re 95% of what I wear!) An oversized sweater feels luxe. Maybe a button-down, but I’d try to avoid anything that leans too Western unless I am in Wyoming (where I often am). Then I’d fully lean into the look, with a bandana, to boot! They would also look great with a maxi dress, so in the summer I might pair them with my black cotton sundress. (I do own dresses, I just rarely wear them!)
Was it a splurge or a save? Another splurge, despite also being on super-sale. But I trust my gut enough now to know that when something stops me in my tracks, it usually means I’ll find a way to wear it enough times to make it a save in the end.

Lindsay’s ADORABLE boots are sold out, but here are some other fun options!

from left: cream, black, tapestry, black w/blue flowers

From black blazers to floral cowboy boots…what did I tell you!? Duality at its best. I also recently found out Lindsay is a fellow Gemini and IT ALL MAKES SENSE NOW! No matter your zodiac sign, we all have multiple ‘sides’ of ourselves and I just love seeing and hearing about each of yours!

A giant thank you to Lindsay for taking time out of her very busy week to chat with me. I hope you all enjoyed this extra special glimpse into her wardrobe and personal style as I did. Please give her a subscribe if you don’t already- I promise you won’t be disappointed! Until next week xx

LA Wildfires Recovery: Please consider donating to the Los Angeles Regional Food Bank, who is working with government agencies and nonprofits to respond to the fires throughout Los Angeles County and provide food and resources to those who are still displaced.

I use affiliate links where applicable throughout my posts, so I may receive a small commission from things you buy (but at no cost to you!) Thank you for supporting me in this little way so I can keep writing every week!