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!

2 Style Tips Regarding Shoes

Style Tip #1:

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

Style Tip #2:

With a dress, nude shoes look like bare legs even if you’re wearing sheer hose. This is also a leg lengthener.

A Guide to Shoes:  How to Choose According to What You Wear

The following clothing categories list clothing items in alphabetical order to make it easier for you to look up modern ways to choose footwear. Age doesn’t matter when you’ve got style.  😉

Which to Wear with Dresses or Skirts

Black dresses:  Add style with leopard-print footwear.

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, perhaps biker boots in brown or black. If cool, add tights.

Flowing skirts:  black biker 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 or gladiator sandals.

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

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

Midi skirts:  try ankle boots that meet the hem for a modern look.

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 #1 — 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.

Ruffled, gauzy skirts:  Birkenstock sandals for foot health.

Sexy dresses:  strappy heeled sandals or stilettos.

Sheer maxi skirts:  espadrilles.

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. Or for more comfort, try  Converse sneakers.

Sundresses:  Try them with espadrille wedges.

T-shirt dresses:  Birkenstock sandals.

Tulle skirts:  gladiator sandals or Converse sneakers when dressing it down (such as a tee & denim jacket.)

Which to Wear With Pants

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

Black pants and a button-down shirt or similar staples:  Pair with their opposite, such as Converse sneakers.

Chinos:  During warm weather, try Birkenstock sandals or gladiator sandals.

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 sneakers, gladiator sandals, wedge sandals or ankle boots.

Gauchos:  A flat sandal or chunky platform goes with cropped pants, not a skinny heel. Gladiator sandals are a good match.

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, gladiator sandals or strappy heeled sandals.

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

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

Leggings:  Try Converse sneakers in the same color, or 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.

Pantsuit:  Converse sneakers for a laid-back look.

Skinnies:  Try slip-on sneakers. Outfit idea #1 — 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.

Track pants:  Converse  or other sneakers.

Wide-legged trousers:  Wear with oxfords or Converse sneakers, depending on whether you want to dress them up or down.

Which to Wear with Jeans

Ankle jeans:  gladiator sandals.

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.

Roll your jeans up and wear with wedge heels.

Slip on some flat espadrilles or strap on some gladiator sandals.

Leopard-print footwear adds style to jeans and a tee; Birkenstock sandals are a classic casual outfit formula with jeans and a tee.

Wear Converse sneakers and a blazer with your jeans. Outfit idea #1 — 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): 

Wear with kitten heels, stilettos, sneakers, flat sandals, flat espadrilles or pointy flats.

Try wearing with riding boots over them. Or, wear with other boots — tall or short. 

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 idea — A loose sweater or a delicate pastel blouse + boyfriend jeans + loafers.

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

Stovepipe jeans:  Wear oxfords, preferably in the same color as the jeans or toned to the color of the jeans. Example:  black stovepipe jeans with black 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.

Oversized clothes:  Converse sneakers.

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.

Which to Wear with the Color of Your Outfit

With Dark Burgundy, Forest Green and Darker Grays: Choose tan footwear.

With White, Ivory, Cream, Tan, Taupe Grays, Black and Animal Print:  Wear brown footwear.

 Miscellaneous

Co-Ords (matching top & bottom sets):  flat sandals or slides, ballet flats or sneakers.

A leather jacket:  Converse sneakers.

Native American Turquoise Jewelry:   choose brown suede footwear and handbag.

About This Guide to Shoes

I listed this guide by clothing and accessories in alphabetical order under each category in order to give footwear choices for the outfit of the day. I’m keeping a copy of this for myself and you’re welcome to do the same! I hope this inspires new outfit combinations for you, which is the basic purpose of this blog. With more creativity, you can buy less. That has always been my motto.  ; )

Let’s Connect!

I hope this was helpful to you. Are there footwear choices you’d like to add? I’d love to hear from you. Please leave a reply in the comments below!

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