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Adrienne Luther

10 Great Ways to Sport Some Saddle Shoes

So you’ve just snagged your first pair of classic saddle shoes. They’re white and tidy and the stitching is just so… Ooh, you’re giddy to wear these little retro ditties out on the town! But with what? Don’t worry, we’re here to provide some guidance on how you can rock your saddle shoes with just about any outfit – daywear or nightwear.

There are a few shoes in history that are truly immortal in the style world. Among the ranks of Converse and boat shoes are the saddle shoes. With remarkable versatility, the saddle shoe can complete any outfit if styled correctly. Let’s take a look at some tried-and-true ways you can rock your new kicks.

Before we get rolling on style inspo – let’s outline a couple of saddle shoe best practices to prevent any faux pas. Here are some ground rules for your shoes:

  • If you’re donning them with shorts, make sure your socks are a reasonable length, otherwise you’ll give the illusion of clown shoes. That means opting for anklets, bobby socks, or low rise socks.
  • Another great way to ensure you’re not lookin’ like a clown is to measure where your pants fall in relation to your footwear. If you’re donning some bell bottoms, for example, you’re likely to look a little clunky. Try to stick with some cuffed skinny or bootcut jeans. This also elongates your legs – if you’re wearing wide legs, these shoes can make you look a little stubby if you’re on the shorter side.

Now that that’s out of the way, let’s look at some inspiration to get you started with your new pair of saddle shoes!

The Go-To: Retro Casual

This look is great if you’re going for a rockabilly or retro influenced look. Pair your saddle shoes with some cuffed skinny or boyfriend jeans, some hoops, a bandana (and lipstick to match!), and a slouchy graphic tee. This is a great starting place for your look – jeans and a tee shirt are your best bet for complimenting your new shoes.

Get Classy with a Pencil Skirt

This look is great for a night out – especially if your heel years are over or if you’re shooting for a bit more casual class. To assemble this look, you’ll need a pencil skirt (here we’ve selected a nautical, high-waist, red wiggle skirt) and a button down. For a rockabilly feel (and to highlight your curves), try tying the button down in a knot in the front. Pop the collar to go full-on Rizzo.

Maybe Go for a Little Grungy...

This look is great for a concert or a trip downtown. Pair your saddle shoes with some black boyfriend jeans, a Beatnik-inspired top (here we have a trendy off-the-shoulder blouse), and some classic Ray Bans. This looks is pretty easy to assemble. Wear your shoes long enough to go full grunge with some scratches and smudges.

For When You’re Feeling Classic…

For a truly youthful look, opt for a playsuit. Rompers and jumpsuits are very in right now – albeit rather impractical when it comes to bathroom trips. These one pieces are in and out of fashion forwardness, but right now is your chance to don a cute little get up with your saddle shoes. Even Marilyn Monroe sported the playsuit back in the ‘60s. Make sure your playsuit falls high enough above your knee to give your legs some visual length. This outfit is a splendid opportunity to sport some true vintage wear – there are several thrift stores that carry playsuits and rompers. Bobby socks are your best friend – they’re not too high and not too short, falling just on your ankle!

For a Summer Day…

For this outfit, you’ll need a crop top and a flowy A-line skirt. What’s great about this style of skirt is that it gives the illusion of a bold hourglass shape by resting right above your hips – highlighting your waist. If it’s spring or fall, complete this look with some darling tights, like these from Modcloth. If you’re not feeling the crop top, this skirt looks great with just about any top – even sweaters.

An Ivy League Look

For this ‘fit, you’ll need to get smart. Well, you’ll at least appear smart with your tweed and button down. To add some sex appeal, opt for one less button than your usual school uniform and accessorize with a simple choker. A simple pearl should do the trick. Historically, the school uniform was one of the first places saddle shoes would make an appearance – if you’re into vintage, now’s your chance to really hone your thrifting skills and assemble a truly retro look.

Always Flattering: High Waisted

Another great way to accentuate your curves and achieve a cute retro vibe is by donning some high waisted shorts or pants with a blouse. If it’s hot out, opt for a flowy top and shorts – the higher the hemline, the longer your legs will look. To really cinch your waist, snag a belt to give a better illusion of a true hourglass form. For a modern, casual look, tuck just the front of your shirt in. A great trick is to gather the front fabric, twist it up just a bit, and gently tuck it in your shorts. Here’s a great tutorial. If you’re going vintage, you’ll have great luck snagging some high waisted jeans from your local thrift store. You can cut the jeans down into shorts, too.

Ready for the Picnic

For a classic feminine look, look no further than a simple A Line dress. Do your hair up in a pin-up updo, tie it up with a bandana, slip on your bobby socks and saddle shoes and you’re good to go. This look is absolutely timeless. To find a dress like this, you’ll have great luck at just about any dress shop or thrift store. This dress is also incredibly easy to sew if you’re a beginner – check out a tutorial here.

Have more ideas on how to style your new saddle shoes? Give us a shout, we’d love to feature more unique looks! 

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