Guide to Shoes: How to Choose Which to Wear With Your Outfits

I have wished in the past that I had a guide to shoes so that I could easily choose which to wear with my outfits. Over time, I’ve accumulated a list of ideas to make it easy…Because a girl has to have the just the right finishing touch, even with a basic everyday look! Shoes are an accessory you can’t go without very often.  🙂  And they make a big impact.

There are some creative combinations below that you may want to try. On the other hand, this is by no means a comprehensive list. Nevertheless, there are so many options here that there’s a good chance they will be helpful to you.

Feel free to print out this listing and keep it in a handy place to refer to when you need inspiration!

Style Tip:

When wearing fun patterned tights, you can make them classy by wearing knee-high boots. Age doesn’t matter.

A Guide to Shoes

Which to Wear With Dresses or Skirts

Bohemian dresses (tribal prints, fringes, peasant style, bell sleeves, free flowing):  Wear with sneakers, lace-up sandals, Birkenstock sandals, platforms, peep-toe booties or suede booties.

Casual dresses (a dress that’s not too formal or sophisticated) or a chic dress with a denim jacket or hoodie or casual vest:  Wear sneakers.

Dresses or Skirts:  Ankle boots are a great option. For summer dresses and skirts, try kitten heels. Or, try slip-on sneakers. Outfit idea — A black skirt + a black turtleneck + animal-print slip-on sneakers.

Go for more fitted shoes with maxis but the shorter the skirt, the chunkier you can make your boots/shoes.

Try riding boots. The hemline should stop at the top of your boots, which will call attention to them. Then you could add tights and a cute top or sweater that complements the overall outfit.

Dressy frocks:  Contrast with combat boots.

Edgy chic dresses:  Unless you want to tame it with classic pumps, it will go with ankle boots, edgy sandals, studded sandals, t-strap sandals or edgy boots.

Floral dresses or skirts:  Try boots.

Full A-line skirt:  Try riding boots, especially with a fitted blouse and pretty pearl jewelry.

Lightweight (Spring/Summer) Dresses:  During transitional weather, try pairing with biker boots or rocker boots or combat boots.

Maxi dresses and maxi skirts:  Try them with espadrilles.

Maxi dresses, shorter skirts and sundresses:  Wear with heeled espadrilles.

Maxi skirts:  Pair them with ankle boots, knee-high boots, flat shoes, flat sandals, ballet slippers or backless slide-on shoes.

Peasant Skirt:  Wedge heels, especially with a feminine blouse.

Pencil skirts:  Wear with kitten heels, pumps or heels of your choice, even loafers. Here’s a way to wear flats:  try slip-on sneakers! Outfit idea — A short black pencil skirt + a graphic tee + a black blazer + leopard-print slip-on sneakers. Add a chunky gold bracelet + silver rings + a cross-body bag. Outfit idea #2 — To shake up your office attire, wear a pencil skirt or belted knee-length dress with loafers.

Retro or vintage dresses:  Modernize them with modern & edgy footwear. Or, stick with the vintage feel by wearing chunky heeled sandals or ballet flats in neutral colors.

Romantic and flirty dresses: Wear classic pumps in a neutral shade or heeled sandals.

Sexy dresses:  strappy heeled sandals or stilettos.

Shirtdresses:  With a shirtdress unbuttoned at top and bottom, belt it and wear over-the-knee boots.

Slip skirt or slip dress:  These flow beautifully over Western boots.

Sundresses:  Try them with espadrille wedges.

Which to Wear With Pants

Ankle pants:  Wear pumps or flats. Or, try slip-on sneakers with ankle pants and no socks.

Fitted pants:  Wear riding boots over the pants. Why don’t you try this with a blouse & blazer?

Flares:  Wear with white cross-trainers, Converse, gladiators, wedges or ankle boots.

Gauchos:  A flat sandal or chunky platform goes with cropped pants, not a skinny heel.

Harem pants or joggers:  Wear any kind of sneakers, wedge sandals, high heels, kitten heels, pointy-toe pumps, classic pumps, flat thong sandals, lace-up flats, or strappy heeled sandals.

Joggers:  Wear with booties, sandals, high-tops, moccasins or oxfords.

Leather pants:  Try slip-on sneakers (a leopard-print would be great!) P.S. I recommend faux leather in order to be kind to animals.

Leggings:  Try flat ankle boots with leggings and an oversized sweater.

Wear riding boots over the leggings with a tunic. Or, try riding boots over the leggings with a tunic dress.

Leggings, skinny blue jeans, straight-leg jeans, or straight-leg pants:  Try pairing with oxfords. Outfit idea — Add a voluminous breezy blouse, boyfriend cardigan, boyfriend blazer, or cropped jacket and opaque knee-high stockings.

Palazzo pants:  Wear with espadrilles or open-toe shoes footwear. Or try wedges, dressy thong sandals, heeled sandals, skimpy delicate flats or ballet flats.

Pants, especially wide-legged:  Wear kitten heels, chunky-heeled sandals or pointy-toe flats.

Skinnies:  Try slip-on sneakers. Outfit idea — White skinnies + a neutral top, such as grey + a bomber jacket + animal-print slip-on sneakers. Maybe add a big silver ring. Outfit idea #2 — White skinnies + a white top over it + a black blazer + slip-on sneakers. Or reverse it with black skinnies + a longer-length black top in the same shade of black or made of a different texture + a white blazer + slip-on sneakers.

Skinny trousers:  Try gold flats.

Wide-legged trousers:  Wear with oxfords.

Which to Wear With Jeans

Blue jeans or khakis:  Brown or black Indian moccasins can take the place of tennis shoes. Or wear loafers, sandals, booties.

Bootcut jeans:  Riding boots may be worn under bootcuts.

Jeans:  Try with loafers for a vintage appeal. Add a pop of color with gold or red flats. Or, try rolling your jeans up and wearing with wedge heels. Slip on some flat espadrilles. Outfit idea — A blue graphic tee + blue jeans + a jean jacket + flat espadrilles. Outfit idea #2 — A button-down + frayed skinny jeans + loafers. Outfit idea #3 — An oversized sweater or cardigan over jeans + a matching fedora + loafers

Jeans or chinos:  Wear with white sneakers.

Jeans or other pants:  Try flat loafers.

Skinny blue jeans:  Try pairing with oxfords.

Skinny jeans or jeggings (jean leggings):  Try wearing with riding boots over them. Or, wear with other boots — tall or short, kitten heels, stilettos, sneakers, flat sandals, flat espadrilles or pointy flats. Of course, loafers or oxfords look good when you’re wearing a preppy top. Outfit idea — Try a blue graphic tee with blue jeans, jean jacket & flat espadrilles. Outfit idea #2 — Try a long grey or black tee over skinny jeans with animal-print slip-on sneakers. Top with a moto jacket. Outfit idea #3 — Try a long white t-shirt over black skinny jeans + a moto jacket + slip-on sneakers. Add a cross-body bag with a chain link handle. If sunny, add sunglasses.

Slouchy boyfriend jeans:  Try with loafers. Outfit ideas — A loose sweater or a delicate pastel blouse + boyfriend jeans + loafers.

Straight-leg jeans:  Wear slip-on sneakers, flat espadrilles or oxfords.

White jeans:  Try neutral, flat sandals.

Which to Wear With Other Bottoms

Anything:  Mules go with everything.

Denim bottoms (jeans or skirt):  These are great with espadrilles or Western boots. Try kitten heels and a t-shirt. With a denim skirt, try biker boots or rocker boots or combat boots, maybe wearing tights to keep a long unbroken line.

Denim overalls:  Try them with loafers for the ultimate off-duty look.

Shorts:  Pair them with flat espadrilles or loafers, especially with jean shorts! Outfit idea — A white tee + jean shorts + a colorful jacket + flat espadrilles + a delicate necklace & bracelets. Outfit idea #2 — Denim shorts + a floaty, summery top + a sunhat + loafers.

Let’s Connect!

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Angie

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