Style Advice Q & A

What Shoes to Wear to a High School Reunion?

There’s always some panic around what to wear to your high school reunion. You want to look fab, but you want to feel comfy too, especially when you will standing around for hours getting caught up with old friends. Here’s an email from a reader worried about what shoes to wear. Can you relate?

wrap dress high school reunionDear Deborah,

I’m planning to wear this black wrap dress to my 45th class reunion and have decided that I probably can’t handle the high-heeled shoes I bought ( similar to the ones in the photo) for the whole night. Also, our community here is VERY casual.  

What shoes should I wear? I was thinking of black ballet flats, but I don’t want to look short and frumpy. I’m only 5’2″.  The heels look great, but I’m afraid I’ll end up barefoot after 3 hours. Thanks, Sara

Hi Sara,

This is such a pretty dress that it would be nice to wear a feminine shoe with a bit of height.

Block Heels are Comfy and Stylish

Why not try a  1 to 2.5-inch nude colored block heel sandal?  It will give you the height you need, plus the chunky heel is better for your foot than a stiletto because it has a greater surface area across which to distribute your body weight.

I like the choice of a nude shoe because it will also help you look taller than a black or a colored shoe. A nude shoe in the shade close to your own skin will blend in with your legs making them look longer, and you look taller.

(For those not concerned with the height you may prefer black (elegant), or to even pick up on one of the colors in the dress such as fuchsia- fun.

Wedges are a Possibility

Another shoe possibility is a  low wedge.  For example, a  nude closed-toe wedge. A wedge shoe is also easier on the feet than high heels. They are not as fashion forward at the moment as block heel sandals but are classics that do work.

Kitten heels are also in style. While low, they are generally not too comfy standing for long periods because of the thin heel. You’d have to test out a pair.

Sara followed up to ask what she should wear on her legs if anything & if black tights were o.k.? Here’s my advice:

Pantyhose/Tights and Open Toe Sandals Don’t Work

Unfortunately, pantyhose or tights worn with open toe sandals look dated and frumpy.  I’d suggest that if you are going to wear an open-toe sandal, you find a good faux tanner to give your legs a hint of color.

If you go with a closed toe shoe such as a closed toe wedge, slingback or pump, then yes you can wear ultrasheer stockings (or bare legs).  I like Donna Karan’s Nude collection of ultrasheer stockings. They are very transparent and natural. You’ll find them sold in most department stores.

dark hose and nude shoes
Dark hose with nude or light shoes doesn’t work. Wear sheer hose with nude or light shoes.

As for black tights, no, they’re too heavy and dark to wear with nude or light-colored shoes, whether they be an open and closed toe.

Can You Wear Black Tights with a Wrap Dress and Black Shoes?

I find most times when women try to wear opaque or semi-opaque black tights with black shoes with a silk/ jersey wrap dress they look off-balance. In other words, bottom heavy.

Opaque black tights can sometimes work with a wrap dress if you have some black in your dress, and you pair the tights/dress with high black high boots.  It’s one of those things where you have to try it on and see if you look weighed down.

Dark tights look best worn with a medium to heavy weight knit dress and dark shoes, boots, or booties.

Your high school reunion is a special event, and it is warm out, so I’d stick to a nude shoe and either bare legs, or ultra sheer nude colored stockings if you are wearing closed toe shoes. This the best choice to make you look feminine, tall, slim and stylish.

Have Fun!

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4 thoughts on “What Shoes to Wear to a High School Reunion?

  1. I have a question about the current summer sweaters that are very loosely woven, requiring a cami underneath. I have 2 I love – one white and one beige. They are a bit slouchy and fun and go with many bottoms. I wear a white cami under each of them, but could I wear a nude color cami (not for work)? Or would I look naked behind the sweater? What about a colored cami, like navy or black? Or would that look harsh?

    1. Hi Karen,
      I have a gold metallic mesh top, and I wear a beige camisole under it, and it does not look like I’m naked. It just all blends in. I think the most flattering look for work is white on white or navy on navy etc., because then you get a bit of the mesh look without it being too much. It’s more conservative. I’d save the two-tone for weekends. It’s a more playful look. I hope that helps. Cheers! Deborah

  2. Hi Deborah:
    I wondered what style of boot to wear if you have heavy knees. Could one wear a mid-calf 2″ heel with leggings, skirts, or jeans and still be stylish?
    Thank you

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