How I’m Styling These 3 Mainstay Boot Styles
What Are We Wearing?
As temperatures drop, boots become more than a staple, they’re the statement. Whether you’re dressing for work, weekends, or an evening out, the right pair can anchor your look, elongate your silhouette, and transform your mood. Below, I’m breaking down the three essential boot styles every wardrobe needs this season — the bootie, the knee-high, and the over-the-knee — plus my favorite way to style each.
1. The Bootie
Create a polished workday look with tailored cropped or ankle length trousers, a silk blouse with a vest or sweater layered on top and finished with structured leather booties. This updated classic look works well with the cropped hem allowing just enough ankle to elongate your leg line while keeping the look office-appropriate. A sleek bootie will ground the outfit with polish while remaining wearable from the desk to dinner. Throw on a funky sock or pattern trouser sock to add some character.
Tara’s Style Edit:
A little ankle goes a long way showing a subtle break between pant and boot keeps the look tailored, not bulky.
2. The Knee-High Boot
This boot is a wardrobe hero with its high versatility. Take a flowing midi dress or skirt with a thick belt and sleek leather knee-high boots for a sophisticated look that's effortless. The taller style boot balances the fluidity of the dress or skirt, grounding the silhouette. This pairing feels like a nod to classic femininity with modern confidence.
Tara’s Style Edit:
When pairing boots with a midi, keep just a hint of leg visible. It's the sweet spot between feminine and commanding.
3. The Over-the-Knee Boot
A chunky sweater dress with black suede over-the-knee boots and a crossbody bag screams I’m stylish, put together, and ready to take on anything. It’s cozy meets sleek with the extra tall boots adding contrast, structure and a little edge to an otherwise soft silhouette. It’s an easy formula for warmth and sophistication that works for brunch, errands, or date night.
Tara’s Style Edit:
Balance proportions when your boots are bold, your dress should feel effortless and un-fussy.
