7 Outfit Ideas with Tall Boots: Filling the Gap in My Wardrobe
I’d like to preface this by saying this isn’t an ad or a promo. This is me genuinely searching for something I needed in my wardrobe and wanting to share the journey with you!
I’ve been on the hunt for a pair of classic black tall boots for what feels like forever. Every fall, I tell myself I’ll finally invest in a pair, and every fall, I somehow put it off. But this year, I noticed a real wardrobe gap. I didn’t own a pair of nice heeled boots that could take me from day to night, from errands to dinner.
So I made it my mission.
I was open to spending around $200, a range that felt reasonable for something timeless but still well-made. Unfortunately, most of the styles I loved were far beyond my budget, and I didn’t want to compromise on quality for something that would fall apart after a season. So I went on a little shopping journey.
After visiting 2 different malls and trying on what felt like dozens of pairs, I learned something important about myself: I have wide calves. And I learned it the hard way (let’s just say I got stuck in a few pairs of boots more than once). Maybe it’s all my daily hot girl walks and Cody Rigsby Peloton classes, but these calves mean business.
Then, after searching high and low, I finally tried on a pair I’d already featured a few times in my style guides: the Sylvia Boots by Sam Edelman.
And I instantly knew they were the ones.
I love their sleek structure, refined but not too stiff. The heel height is perfection: not a stiletto (hello, ankle rolling) and not a chunky block heel (been there, done that). It’s a slim, modern block that gives you that lifted look while still feeling stable. For sizing, I went with a 7 (my usual) and chose the wide calf version for extra comfort.
I’ve worn them around the house and while shooting content, and so far, they’ve been incredibly comfortable. I can’t wait to take them on a proper outing to test them even more, but in the meantime, here are 7 easy outfit ideas featuring my new tall boots!
7 Tall Boot Outfit Ideas for Fall
You can shop all the pieces here! Some items might be out of stock, but I’ve done my best to link similar options. You’ll also find everything linked below in each section so you can easily recreate the looks.
1. The Classic Mini & Jacket Combo
A brown houndstooth wool jacket, a black mini skirt, and sheer black tights. Simple, timeless, and endlessly chic. The structured boots add polish without feeling overdone.
2. Sweater Dress & Trench
A cozy brown knit dress layered under a beige trench. Effortless, warm, and perfect for a coffee date.
PS: This knit dress is by Maison Stella & Suzie, a super cute French brand. If you haven’t heard of them yet, I recommend reading my post about them! It’s one of my favorites!
3. Pleated Skirt & Trench
This look brings Parisian movement to fall dressing. The pleats create beautiful texture against the sleek silhouette of the boots.
4. Cream Cardigan & Black Skirt
Soft contrast at its best. The cream knit keeps things light, while the boots ground the outfit for that transitional weather vibe.
5. Brown Knit & Satin
A monochrome mix of rich chocolate tones layered under a trench. The texture contrast between satin and leather feels elevated yet wearable.
6. Monochrome Elegance
A pleated midi skirt and structured blazer with gold buttons. Proof that monochrome black doesn’t have to be boring. It’s sharp, feminine, and quietly powerful.
7. Slip Dress & Trench
For an evening spin, the same boots feel unexpectedly refined with a brown satin slip dress and classic trench coat. Add sunglasses for that “off-duty Paris” energy.
Looking for Boots This Fall/Winter?
If you’re still searching for the perfect pair, here are a few others I’m loving right now, from classic silhouettes to modern takes on the tall boot. Whether you prefer sleek leather or a softer suede finish, these are all picks that blend timeless style with comfort and versatility!
Final Thoughts
Finding the right tall boots can take time, but once you do, they become one of those anchor pieces that tie everything together. From minis to midis, from coffee runs to evenings out, they add just the right mix of polish and practicality.
If you’ve been putting off finding your pair, consider this your sign to finally do it. The perfect boots don’t just complete an outfit, they elevate it, giving every look that effortlessly chic, put-together feeling we all love!
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With Amour,
M.