The best shoes depend on the overall look you’re going for. For a classic, professional vibe, heels (pumps, stilettos, or kitten heels) are always a good choice. For a more casual or modern look, consider round flats, loafers, or even sneakers (depending on the skirt’s material and the occasion). We’ve got some great examples of different shoe pairings in this article on Brunette from Wall Street!

Ankle boots. You can’t wear ankle boots with a pencil skirt.

Yes! Pencil skirts aren’t just for the office. Pair a denim or jersey pencil skirt with a t-shirt and loafers for a relaxed weekend look. Or try a knit pencil skirt with a cozy sweater and suede boots for a chic, everyday outfit. Check out our styling tips on Brunette from Wall Street for more casual pencil skirt inspiration.

From blouses and button-downs to sweaters and t-shirts, the possibilities are endless! Tucking your top into the skirt creates a defined waist, while leaving it untucked can create a more relaxed silhouette. The key is to consider the fabric and style of both the top and the skirt. We’ve styled pencil skirts with a variety of tops in this article on Brunette from Wall Street – take a look!

The ideal length depends on your body type and personal preference. Generally, pencil skirts that hit just below the knee are flattering on most figures. Shorter pencil skirts can be fun and flirty, while longer ones can be very elegant. Explore different lengths and find what makes you feel most confident. You’ll see a range of lengths in the outfits we’ve put together in this article on Brunette from Wall Street.

Unlikely. The key is finding the right fit and styling it in a way that flatters your figure. High-waisted pencil skirts can be very flattering, as they define the waist and elongate the legs. Don’t be afraid to experiment with different styles and fabrics to find what works best for you.

We’ve linked many of the items featured in this article directly in the collages. Check out the outfits to find the perfect pencil skirt for your wardrobe!

Winter opens up numerous styling possibilities. Layer with a cozy sweater or cardigan, add warm tights, and complete the look with knee-high boots. A winter coat can add both warmth and sophistication – just make sure the coat is longer than the skirt, while a tweed jacket offers a perfect middle ground between style and comfort. See more winter pencil skirt outfits curated by Brunette from Wall Street.

Modern pencil skirt styling is all about unexpected combinations. Mix classic pieces with contemporary elements – try pairing your skirt with a bomber jacket, or dress it down with loafers. The key is balancing traditional elegance with current trends. Check out the latest modern pencil skirt looks on Brunette from Wall Street.