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The Updated Guide to Shoe-and-Pant Pairings

This just in: the best heels, flats, sneakers, and boots to wear with skinny, straight-leg, wide-leg, and cropped pants.

By Emma Steinbergs

Sneakers or stilettos? Flats or boots? These are the styling questions that haunt many a pant purchaser. Thankfully, this guide seems to have solved many of your footwear-based conundrums since its publication a couple of years ago. But since then, we’ve released new styles and further explored Power Casual dressing, so we want to provide you with some refreshed tips and tricks.

With the launch of our new collection, The Founders’ Seven, the time is ripe for this reset. It’s our 10-year anniversary, so it’s only fitting that our first launch of the year blends both ease and elegance—a marriage that is quintessentially M.M. One new style that especially embodies this design ethos is the Skinny Foster.

A tapered take on our all-time best-selling pant, the Skinny Foster features the same beloved PowerStretch fabric, plus faux back pockets, which add coverage and polish, and notched ankles. The result is a sleek silhouette with a whole lot of styling possibilities. In other words, it’s the perfect style to kick off our new pant-shoe pairing guide. Scroll to see the shoes we recommend wearing with skinny pants, straight-leg pants, wide-leg pants, and cropped pants.

The Best Shoes to Wear with Skinny Pants

As we mentioned, the Skinny Fosters have a range of styling possibilities. Why? Because they have a classic cigarette shape as well as a subtle slit detail at the hem that allows you to wear them with shoe styles that hit above your ankle. Depending on your height and shoe, the notched ankles will look different. If you’re more petite, the hem might fall a bit below your ankle, which actually looks extra-chic and is not a hindrance, thanks to the notch. To take advantage of the Skinny Foster’s (and other skinny pants’) elongating effects, our stylists recommend pairing them with pointed-toe shoes, like the Rowan flats and Lana boots, which create the illusion of a longer silhouette. This can also be achieved with streamlined heels like the Ella sandals. Of course, you can never go wrong with polished sneakers in your casual-leaning outfits. Go with the Koio Capri sneakers and Curie pants for a laid-back, leggy look.

The Best Shoes to Wear with Straight-Leg Pants

Straight-leg pants are both timeless and especially popular right now for a couple of reasons: They offer a cool, slightly relaxed look and fit a wide range of body shapes. To create an impeccably balanced outfit, pair your classic suiting trousers, like the Mejia or Smith pants, with a shoe that adds sharpness to your bottom half. Choose from pointy-toed styles like the Irene slingbacks, Lillian pumps, or Ginger pumps, depending on your preferred heel height. We also encourage you to play around with styling your suiting slacks with sneakers for a fashion-forward look you can wear to your business-casual office or your weekend activities.

The Best Shoes to Wear with Wide-Leg Pants

I fell in love with wide-leg pants around five years ago, and I never looked back. The slightly oversized silhouette has a certain je ne sais quoi that makes you look like you don’t have to think too hard about style—you were just born with it. More concerned with the practicality of your pants? Wide-leg pants are just about as easy and breezy as it gets. For equal parts cool factor and ease of movement, try pairing the popular Milo jeans with the leather Koio Capri sneakers or sharp Rowan flats. If you prefer more traditional trousers, opt for the Horton pants, and play around with styling them with anything from sneakers to more formal footwear like the Ginger pumps. Bottom line: If you’re committing to a dramatic pant silhouette, commit. Make sure the hemline hits your foot rather than hovering at your ankle. If you’re petite and worried that wide-leg pants will overwhelm your frame, we have several styles with adjustable hems (including the Milo jeans). Your other options are investing $30 or so to get them tailored and/or ensuring your footwear provides just enough height to keep your hem from dragging.

The Best Shoes to Wear with Cropped Pants

Repeat after me: Cropped pants are not just for warm weather. Rather, they’re another category of pants that, if given a chance, will quickly become a go-to silhouette in your year-round rotation. Take the Archie pant, for instance. This cropped bootcut style adds a bit of flare to summer and winter outfits alike, and in the case of the vegan leather version, gives you an elegant edge. Looking for a tapered leg instead? Try the stretchy, sleek Robin pants. On cold days, we suggest pairing either of these pant styles with sock boots, like the Zeldas, to keep covered and warm. Other foolproof shoe pairings for these elevated yet easy pants include the slip-on Rowan flats and extra-comfortable Koio Capri sneakers. Remember: It’s more than okay if there’s some skin between your pant hem and shoe, so even tall customers can enjoy cropped styles. Just keep your pants no more than a couple of inches above the top of your shoes to avoid looking like you bought ill-fitting pants. Other than that, you’re good to go!

Written By

Emma Steinbergs

Emma is M.M.LaFleur's Brand Manager. She previously worked as an M.M. stylist and still loves thinking through styling challenges and solutions for customers.

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