What Shoes to Wear to a High School Reunion?

what to wear to your high school reunionThere’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.

Here’s an email that went back and forth between a reader and I this week about what kind of shoes to wear.

Dear Deborah,

I’m planning to wear this dress to my 45th class reunion on Saturday night, yes this Saturday— I decided tonight that I might not be able to handle the shoes that I have like the ones in the picture for the whole evening.


Also, our community here  is VERY casual.  What shoes? Black ballet flats? 1″ neutral sandal with a fringed ankle strap?  Black tights and 3/4 ” black booties or buy something else? I’m 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 it would be nice to wear a feminine shoe with a bit of height. Why not try a low wedge? A wedge will give you that height but won’t hurt your feet the way a skinny heeled shoe might. Here are some examples or what you could try.

nude wedge

imgSara followed up with an email asking if what she should wear on her legs, if anything, and if  black tights were o.k.?.

Hi Again, If   you plan to wear these nude wedges  and it’s still warm enough where you live you can wear bare legs if you like, but only if your legs are good ,which means not veiny, marked or pale.  If that doesn’t work for you then sheer pantyhose are perfectly fine. I like Donna Karan’s Nude collection. They are very sheer 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, they’re definitely  too heavy dark to wear with nude or light-colored shoes.

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

Can you wear black tights with a wrap dress if you wear black footwear? I find that most times when women try to wear black tights and black shoes with a silk/ jersey wrap dress they look off-balance – bottom heavy.  It can work 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. Even then, it’s more of an everyday look.

This is a special event so I’d stick to a nude shoe and nude colored legs to make you look feminine and create a long lean unbroken line that makes makes you appear taller and slimmer.

Have Fun!

p.s. Send in a photo if you get a chance.

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  1. Karen Ingram says:

    I have a question about the current summer sweaters that are very loosley 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 a lot of 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?

    • 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 underneath at all. 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. Hope that helps. Cheers! Deborah

  2. Julia Inman says:

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