The Closet Coach

Reader Marni writes to ask, “I never know exactly which shoes to wear with a dress. How do I know what will look the best?”

Great question! I sometimes have this same dilemma myself, so it’s a great opportunity to refresh both of us on some of the guidelines.

(And–as is true of the Pirate Code–they’re really just guidelines. A true fashionista knows how to break every rule in style!)

So here are some tips for choosing the right shoe to wear with a dress.

• Style. Let the style of the dress be your first guide. Is it a summery, spaghetti-strapped sundress? Then don’t wear thick, chunky shoes. Is it a sleek little cocktail dress? Then a cotton espadrille won’t work.
• Season. Match the season of the dress to the shoe. Lightweight spring dress + sandals = yes. Lightweight spring dress + fur-lined boots = no.
• Color. This one can be a bit tricky. You can never go wrong wearing black shoes with a black outfit, but any other color can veer into bridesmaid matchy matchy territory if you’re not careful. This is where the nude pump trend is especially helpful. Or try a bright complementary color, like yellow with navy or red with neutrals.
• Occasion. Where are you going to be wearing the dress? The same black dress might call for a pair of pumps in the office and strappy sandals for an evening out.

Now for the rule-breaking: try several pairs on and see what works. That lightweight spring dress might actually look boho chic with the right pair of boots. Flats might look great with a dress you assumed would demand pumps.

Look around for ideas, too. Fashion editors make very conscious choices of the shoes they pair with dresses in magazine spreads. Outfit posts on style blogs or found in Pinterest can give you inspiration.

And if nothing in your closet works with that new dress you just bought? You now have a golden excuse to go shoe shopping!

What to buy

Marc New York safari dress
$72 - bluefly.com

J Crew Elinor dress
$148 - jcrew.com

Oasis bow back dress
$82, sale - asos.com

Stuart Weitzman Littleneck boots
(no longer available)

Sperry Top-Sider Santa Rosa wedge
$50 - endless.com

London Rebel kitten high heels
$49 - asos.com

Rampage Women’s Malika Pump
$45 - amazon.com

Tommy Hilfiger Tutti flip flops
(no longer available)

Cole Haan FLX Women’s Air Astoria Thong Sandal
$125 - endless.com

[Disclosure: Some links are affiliate links.]

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(Want to get more shopping tips and fun insider stuff? Join The Style List. It’s like a secret club in your email inbox! And when you join, you’ll get my free email series, 7 Days to Better Shopping. It’s my gift to you!)

Like anyone offering style and wardrobe advice, I’ve sung the praises of including a classic, flattering Little Black Dress (LBD).

But after I wrote my post on how to buy a new LBD, I realized I needed to follow my own advice.

The one hanging in my closet was at least 15 years old–and about one size and 4 inches too short. What works at 26 does not always work at 41, n’est-ce pas?

I am here to tell you I feel your shopping pain. Even knowing the kinds of silhouettes that look best on me, I ordered and sent back 6 different dresses from 3 different online stores, no farther ahead than when I started.

Then I discovered Calvin Klein, one of my favorite labels, was having a sale. I ordered 3 dresses, hoping at least one would work–and I kept two.

I should have started at Calvin Klein. After all, another piece of advice I offer is to find which stores or labels work for you and start your shopping there!

This is one of the two dresses. Although it’s dressy enough to wear to a cocktail party, it’s of a softer jersey material and covers enough of the body that it would be entirely appropriate to wear to work as well, especially with a blazer or cardigan on top.

The detail of the criss-crossed V neck works on me because it helps balance my smaller top half with my bottom. The side shirring defines the waist and is especially forgiving of the midsection. And the length hits perfectly just above the knee; short enough to avoid looking dowdy, but long enough to avoid looking inappropriate, especially at the office.

Shoe selection is always tricky in the winter time. Most of my more evening appropriate footwear is a strappy sandal–weird with hose, but too cold to wear bare-legged in February (even if it was mild enough on this Saturday to take a few photos coat-free).

• What do you think? What shoes should I wear with an LBD in cold weather?
• Black hose or tights only? What about a nude hose, a la the Duchess of Cambridge?

Dress: Calvin Klein surplice wrap V-neck sheath dress, $139.50.
Shoes: Nine West (similar, $47, 6pm.com).
Necklace: Tiffany oval tag necklace, $425.
Outfit level: 4/5

[Disclosure: Some links are affiliate links.]

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Thanks for reading. Did you like this post? Please leave a comment or share it with someone else; just use the handy sharing widget below.

(Want to get more shopping tips and fun insider stuff? Join The Style List. It’s like a secret club in your email inbox! And when you join, you’ll get my free email series, 7 Days to Better Shopping. It’s my gift to you!)

Whether you’re dining at the chicest chef’s outpost or simply adding candles and flowers to your own dining room table, the biggest Date Night of the year, otherwise known as Valentine’s Day, is just around the corner.

What’s a chic mom to wear?

Here are some ways you can spice up your Valentine’s Day with an outfit (and an evening) that’s truly a Level 5.

• If you’re going out straight from work. Obviously you can’t spend a day at the office in your LBD. Or can you? Unless it’s cut too high or cut too low (and if it’s both, it’s a bit too much for dinner anyway), make it work friendly by topping it with a fitted blazer or even a belted, beaded cardigan. Wear a strand of pearls and you can keep them on all day. Take off the topper and swap your pumps for strappy heels, and you are Level 5, lady.
• If you’re leaving after the babysitter arrives. Unless your kids are older, you might have to dodge sweet and sticky little fingers up until the moment of your escape, so the LBD is a little less practical. Think sexy top (sequins, low cut, velvet, whatever you’ve got!),  pencil skirt and your blingiest, shiniest necklace. Save the skirt for the last minute, or put a robe over everything, until you hear that doorbell.
• If you’re having your romantic dinner at home. Who says you have to save Level 5 for going out? This is still Date Night, my friend. Sure, you can slip those high heels off whenever you’d like (and you should be taking them off eventually, wink wink), but why save your best dress for a night out?

No matter which scenario is yours, you’re not necessarily limited to a dress or a skirt. Your main goal is to feel fabulous, so wear what you know looks fantastic on you, whether it’s a pair of well-cut trousers or skinny jeans, and include a little skin and a little shine.

Add perfume and heels (how high you can tolerate is between you and your feet–or possibly your podiatrist) and you’re done.

What to buy

Awards Show Stunner Dress in Red
$105 – modcloth.com

Bettye Muller patent leather shoes
$89 - jildorshoes.com

Steve Madden Walltz peep-toe sandals
$90 - stevemadden.com (heads up: free shipping on orders over $75 with code SMFREESHIP for a limited time)

Jessica McClintock quilted clutch
$45 – zappos.com

Moschitto Designs geometric jewelry
$42 - nordstrom.com

Dereon tear drop earrings
$32 - maxandchloe.com

[Disclosure: Some links are affiliate links.]

Your turn

• What are you planning to wear for Valentine’s Day?
• What’s your favorite look for Date Night?

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