How to Choose the Right Shoes for Your Look (VERY Important)

How to Choose the Right Shoes for Pants

Pants is kind of a hefty category because it includes all different styles – jeans, trousers, sweatpants. But even within those types, there’s straight leg, bootcut, flared, high-waisted, low-rise, slouchy, boyfriend, mom jeans. And then on top of that, you have to consider fabric weight or fabric density.

Okay, I made that sound way more complicated than it actually is. Let me break it down with examples.

Bootleg, Flared, and Wide Leg Pants: For these styles, shoes with a more narrow silhouette and toe box tend to look the most flattering. The silhouette of the shoe is more important than the type of shoe. Let me explain what I mean.

If you’re going for a casual look with bootcut jeans, sneakers with a narrow silhouette look better than chunky sneakers. They’re both sneakers, but one style is more flattering because it has the proper silhouette for this pant leg. Same thing with dressy looks – pumps look more balanced with wide leg trousers than chunky heeled shoes.

Skinny Leg Pants: Full transparency, these are my least favorite type of pants. I don’t like wearing them because I have really narrow hips and long skinny legs, so they make me look really imbalanced. But if you have thicker calves, they might look amazing on you!

For people with skinny legs who do like wearing them, skinny pants require a more narrow shoe profile. Basically anything that’s not platformed, thick, or chunky. Skinny sneakers, sandals, knee-high boots, combat boots (as long as they’re not too chunky). You can even wear loafers, but make sure it’s one with a narrow profile.

Straight Leg Pants: These are pretty versatile, but I’d opt for shoes with a lower profile. Choose low-top sneakers over high-tops. When it comes to boots, you can wear boots with a higher shaft as long as the shaft is skinny and close to the calf, because you want it to fit underneath the pant leg. Otherwise it’s going to bunch up around the ankles and look really awkward. It’s just not sexy, you know?

Cargo Pants: With the resurgence of Y2K fashion, cargo pants are super hot right now, and I think they’re actually pretty versatile. Sneakers? Yes, chunky or narrow, doesn’t matter. Sandals? It’s giving army pants with flip-flops. I would even wear them with heels – I love open-toed heels with cargo pants.

Sweatpants: Listen, I love sweatpants. You would have to unalive me before I give up my sweatpants. You would have to pry them out of my cold dead hands. But there’s nuance here that not a lot of people talk about.

There are two main sweatpants silhouettes: slim profile and baggy. These give off very different vibes and require very different shoes. Slim profile sweatpants give off that really put-together, mature vibe. They look nice with an exposed ankle, so low-top sneakers, loafers, ballet flats, even sandals if that’s your vibe.

Baggy sweatpants give off a more cool, young, street kind of vibe. I personally think exposed ankles look really awkward with these, so I prefer high-top sneakers or boots with a higher shaft like Timberlands.

Consider Fabric Weight: The weight and type of fabric can change the entire feel of a look. Wool trousers are more formal and require structured shoes. Linen trousers are casual and lightweight, so you can wear sandals. Different fabrics, different vibes, different shoes.

How to Choose the Right Shoes for Skirts

A lot of people find skirts difficult to style because there are so many factors – length, style, fabric, occasion. But there’s also that added layer of considering your body’s proportions.

A-Line Mini Skirts: These are the most versatile and easy type of skirt to style. Sandals, platforms, pumps, combat boots, high and low-top sneakers – you name it. But different proportions prefer different shoes. Because I have long legs and skinny calves, I can wear crew socks or high boots with mini skirts. But if you have shorter legs and thicker calves, shoes with a lower profile will make your legs appear more elongated.

Midi Skirts: These look great with low-profile shoes like sandals, low-top sneakers, and heels without ankle straps. Midi skirts stop around the mid-calf area, and when shoes have a strap around the ankle, it can make that area look busy.

Maxi Skirts: You really want to avoid high-profile shoes here. Stick to lower profile shoes, nothing too chunky, or else you risk looking very bottom-heavy. Also, if your maxi skirt is long enough to cover your shoes, then you don’t really need to bother with this.

Pencil Skirts: These are a wardrobe staple for so many women, especially ones in corporate environments. They have a very sophisticated feel. I would absolutely avoid sneakers with this type of skirt. If you’re wearing boots, the shaft should be short and close to the calf – like a sock bootie. Pumps are tried and true, but you can also wear strappy sandal heels.

How to Choose the Right Shoes for Shorts

Denim Shorts: These have a very solid casual vibe. You cannot dress these up. Once you’ve put on denim shorts, you have committed to the aesthetic. The obvious options are sneakers and sandals, but you can wear boots too – denim shorts with cowboy boots is really hot right now if you’re into that trend.

Athletic Shorts (Biker, Basketball, Sweatshorts): I honestly would not wear any type of shoe that’s not a sneaker with these. For biker shorts, Princess Diana is the blueprint with crew socks and sneakers. For sweat shorts or basketball shorts, crew socks and sneakers all the way. I’m just a huge fan of that look.

Tailored Shorts: These are way more versatile. To dress them down, go with strappy sandals or crew socks with sneakers. To dress them up, try loafers or even open-toed heels.

But Wait, There Are No Rules

Here’s the thing: there are really no rules in fashion, and you don’t need to follow any of the guidelines in this article if you don’t want to. But I found that my personal style improved significantly when I got comfortable with conventional style rules first. It served as foundational education – it helped me learn the basics before I started branching out and experimenting.

How to Choose the Right Shoes for Your Look

Shoes can make an outfit look expensive or messy in seconds. The right shoe matches the outfit’s vibe and the proportions.

Think of shoes in two categories:

• Line-extending shoes: pointed toe, low vamp, nude tones, sleek silhouettes

• Grounding shoes: loafers, chunky soles, boots, sneakers

Common mistakes:

• You wear delicate shoes with heavy outfits, and the balance feels off.

• You wear chunky shoes with cropped wide pants, and the outfit looks stubby.

• You pick a color that doesn’t connect to anything else.

Quick shoe rules:

• Wide pants love a sleek shoe or a platform.

• Midi skirts look best with shoes that show ankle.

• If you wear a bold shoe, keep the rest of the outfit simple.

Pick shoes first when you can. They control the whole outfit.