Styling Shoes for Every Outfit

I want to answer one of the most common questions I get from clients: “How should I be styling shoes with my outfits?”. I don’t believe there’s any one shoe that shouldn’t be worn with a particular outfit, as long as you love it and feel great in it, that’s what matters most. But, if you’re unsure how styling shoes would work with what pieces, and want some guidance, that’s exactly what this post is here to help with.

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If you’re wearing a dress or skirt that hits at the knee or above, you have a lot of shoe options. You can wear sandals, sneakers, loafers, or even over-the-knee boots if the dress leans more toward fall or winter. If the weather’s warmer, flat sandals also work well and can even dress it up a bit. With something like a t-shirt dress, you can make it more casual with a casual shoe or dress it up with a sandal. It all depends on the vibe you want.

2. At The Ankle

right shoes, styling sessions — whowhatwear

Since many of us have moved away from skinny jeans and are wearing more modern styles like a slim straight leg jean, the question becomes: what shoes work when the jeans hit at the ankle or are slightly cropped? It can feel like it throws things off a bit, but there are still so many shoe options that work.

A classic flat like a loafer, ballet flat, or a chic sneaker can work with pretty much any jean length. These shoes also pair well with different leg shapes. So whether you’re wearing skinny, slim straight, straight-leg, or wide-leg jeans, all of these silhouettes can work with a flat shoe.

3. Wider Jeans

capsule shoe wardrobe, style coach — @aimeesong

I feel like it gets a little trickier when we’re talking about boots. It used to be simple because we’d tuck our skinny jeans into boots, and it worked. But now that jeans are a bit wider, how do we wear boots with them? As long as the width of the jeans around the calf can cover the top of the boot without being tight, it’s fine to wear the boot underneath. Where it gets tricky is when the shaft of the boot is a little wider and the jeans are still on the slimmer side. If those jeans are ankle length or longer, they can bunch awkwardly at the bottom.

What I recommend in that case is doing a small cuff on the jeans and letting them sit a bit undone over the top of the ankle boot. But if that doesn’t work with your personal style, then go for an ankle boot that’s more fitted around the actual ankle, like sock booties. Another great option is to choose a cropped jean that hits above the ankle, paired with a boot that has a lower shaft. That way, the hem of the jeans sits right on top of the boot, and you still get a clean, straight silhouette.

4. Midi Skirt

Now, what about when you want to wear a midi skirt? One of my favorite ways to style a silk midi skirt is with a pair of chic sneakers and a simple tee. I love this look because it’s easy and casual, but the skirt adds a dressier element, while the sneakers and t-shirt keep it relaxed. It’s a great example of styling opposites in your closet by pairing something dressy with something casual.

If you want to dress it up a bit, swap out the sneakers for a flat sandal. That small change instantly makes the outfit feel more elevated. This is one way to make the pieces in your closet work to add more versatility to your wardrobe.

capsule wardrobe shoes, Personal stylist mens — Instyle

If you’re someone who has shorter legs and you want to create a lengthening effect to balance your proportions, a great way to do that is by wearing a nude shoe. Nude shoes help elongate the legs. Especially when paired with anything that hits at or above the knee because they give that visual extension to your bottom half.

Another way to lengthen your silhouette is by matching the color of your bottoms to your shoes. For example, pairing black trousers with black boots creates one continuous line, making your legs appear longer. And opting for a pointy shoe is another easy trick. The pointed toe helps create that long, uninterrupted line from your waist down to the tip of your shoe.

Consider: Your Personal Style

styling shoes, Personal styling for men — @cristinahudacov

The next thing to consider when choosing shoes is your personal style and your lifestyle. If your day-to-day is more on the go, then a flat shoe works best. Whether it’s a chic sneaker, flat sandal, or flat ankle boot, it needs to fit both your lifestyle and your personal style.

Now, even though ballet flats or loafers might work for my lifestyle, they don’t feel aligned with my personal style, so I don’t reach for them. It’s important to take into account what feels like you, because that’s what you’ll end up wearing most.

shoe styling, style coaching — @leasy_inparis

Another question I get asked a lot is, “Do my shoes need to match my belt and bag?” And my answer is no. If your style leans more polished or put-together, then you might enjoy coordinating your belt, bag, and shoes. But that old rule about matching everything doesn’t apply anymore. It’s all about what makes you feel your best.

I always recommend having both a neutral and a black option for every shoe style you wear regularly. That’s what gives you the most versatility in your outfits. Whatever your neutral shoes don’t work with, your black ones likely will.

Expert Tips For Altering Your Hemline To Work With Your Shoes

right shoes, Personal stylist los angeles — @yarashahidi

Unless you’re cuffing the bottom of your jeans for your boot shaft, don’t cuff your jeans or trousers, especially if you’re petite. It tends to look more like you’re trying to make the pants fit than like they fit you properly. Instead, this is one of those times where I highly recommend investing in good alterations or tailoring. If your jeans, pants, or skirts are too long, they won’t work with any shoes you pair them with.

I’ve had clients tell me something is too long and say, “But I can wear it with heels.” The reality is, how often are they wearing heels? If the length doesn’t work with flats and that’s what you wear most, then it’s not practical. Bringing the hemline up means you’ll wear those pieces more often, and that alone makes the tailoring worth it.

1. Bring 2 Shoes To The Tailor With You

You want to bring two pairs of shoes with you to the tailor when you’re trying on your bottoms. One flat that you wear regularly, and one heel or wedge that you also wear. Try on both pairs with the item you’re hemming so the tailor can find a length that works with both. That way, you’ll be able to wear your bottoms with different shoes, which is key to getting the most use out of your clothes.

2. Keep The Original Hem On

The next tip is if you’re hemming jeans, ask the tailor to “keep the original hem on”. That means the stitching at the bottom will be preserved. That can make them look less polished and more obviously altered.