What To Wear To Look Hot at Your High School Reunion (without trying too hard)


Reader Question:

I’m attending my 25-year HS reunion in 2 months and am wondering what I should wear to the Dinner/Dance? I want to look hot without seeming like I’m trying too hard.


Ah…yes.  The high school reunion.  Where you want to look totally, wildly hot…but in an effortless way.  Where you fend off compliments with a dismissive wave of your hand, “this old thing?  I’ve had it for years.”

So what to wear?  If you Google, “what to wear to your high school reunion”, most of the advice centers on the little black dress.  LBDs are always appropriate for these types of events, and if you have one you love, go nuts.  However, the LBD isn’t the most imaginative choice.  I’m assuming that you are writing in because you are looking for something beyond the obvious.

When I want to appear effortlessly glamorous, I turn to a mix of fancy and casual pieces.  The combination, when done correctly, results in a casual sophistication — you look like you just threw it all together, but in a perfectly imperfect way.

So here are a few ideas for looking hot at the high school reunion, without looking like you busted out your best pearls and sweater-set.

1.  Go For Easy Glamour in a Maxi Dress


What To Look For:

To make the maxi dress totally hot, look for lower or interesting necklines.  These types of necklines will also photograph well.  Also look for maxi dresses that skim over the body – nothing too voluminous.  You want a maxi dress that evokes images of an old Hollywood screen siren at the Oscars…but in a casual fabric (to keep the vibe effortless).  Maxi dresses with too much volume can start to look like something Laura Ingalls Wilder would wear to gather up woodchips in the Big Woods.

Gypsy ’05’s Alex Silk Maxi Dress , currently on sale for $139, (and pictured above in a soft yellow) has a nice narrow fit, a great bustline, and a slightly higher waist which will help to hide belly-poochiness.  The washed silk is both casual and glamourous.

I’m also loving Victoria’s Secret’s Halter Bra Top Maxi Dress, $89.  This dress’s dramatic neckline would look amazing in photos, the built-in bra helps support the ‘girls, and while the dress is a bit more voluminous, the sexy peek-a-boo back and amazing overall drape keeps this maxi dress hot.

Lastly, Rachel Pally’s Two-Tone Halter Dress, $233 at shopbop.com, is totally, wildly, glamourous, but has a casual vibe that makes it wearable everywhere. This dress can be worn multiple ways, and has a crazy-sexy back.

How To Accessorize:

In terms of shoes, stick to either fancy flats or wedges, as pictured above.  Anything else tends to look too formal (or stuffy) with a casual maxi dress.

I’d carry a simple clutch, and add an armful of bracelets and amazing earrings.  I think necklaces would compete too much with the fab necklines of these dresses.

2. Show Some Leg in Fun, Flirty Summer Dresses


What To Look For:

When in doubt, go short.  But to keep the overall vibe easy and effortless, stick to either drapey knits, or casual fabrics like cotton and linen.  You want a sex-pot silhouette in a girl-next-door fabric.

I love one-shoulder dresses for their instant sophistication.  And you’ll look amazing in pictures.  Susanna Monaco’s One-Shoulder Drape-Front Dress, pictured above in blue, is the perfect combination of drapy silk fabric in a belly-hiding, leg-showing, hot little number of a dress.  This dress retails for $275 at piperlime.com.  J. Crew’s soft violet Poplin Bridget dress, currently on sale for $118, would also work, but unless you are model tall, I’d prepare to hem this dress.  It hits perfectly on the model, but tends to run long on regular gals.

If one-shoulder isn’t your thing, I also love simple little strapless dresses for their picture-worthy necklines and flattering silhouettes.  To illustrate, we’re showing Banana Republic’s punchy pink number in linen, or J.Crew’s too-die-for floral strapless sheath in the picture above.  Either of these would be flawless choices.

How To Accessorize:

If you are a hard-core flats girl, metallic strappy gladiators (like the J. Crew model in the one-shoulder dress) would be a perfect choice.  Else, I’d stick to high strappy sandals.  Avoid serious pumps with these dresses.  You want to up the flirty vibe, but still keep things easy.

For those dresses with a waist, I love to add a skinny little belt.  With belts, keep the rest of the jewelry simple:  fab earrings and a chunky cocktail ring will add a bit of bling without going overboard.

If you go the strapless route, statement necklaces can be fun, but I’d be careful with the belt.  Both can quickly become overkill.

Your bag?  Stick with a slim clutch.

3.  Go Nude!!



What To Look For:

Well, not just nude, but various tones of white, cream and blush.  You can always work a “naked dress” (wasn’t that a Sex and the City episode??) like this one or this one…but I also wanted to highlight a reunion-worthy option that involves pants, for the skirt-shy.

I love white pants in the summer.  They are always classic and glamorous, (but not really mom-friendly with a little one around…so I save them strictly for date-nights).  My favorite white pants are a bit menswear, trouser inspired, but find some that work for you.  Just be sure to look for white pants that are not too sheer, and wear a nude-colored thong underneath.

Next, add a sexy top in any pale, nude, shade.  White-on-white, white-on-cream, white-on-nude, or blush are all amazing combinations.  Look for tops with low necklines, amazing drape, and a little extra something-something:  sequins, ruching, lace.  Layer over a nude bra (strapless is best) or nude cami.

How To Accessorize:

When the palette is so soft, I love to go nuts with metallic accessories.  Think chandelier earrings, long drapey necklaces, stacks of arm candy and metallic shoes.  Mix metals with wild abandon.

And the final touch?  Sheer red lips.  This look is especially gorgeous with a slight tan.

Good luck!




  1. I absolutely LOVE this post. I’m digging all of it. Wish I had read it last year before my reunion!
    NOTE for readers: True Love in Denver on Broadway is a fun shoe store (and accessories) with outrageously great prices. They have a wedge sale going on right now – all wedges $22. Hello – can’t beat that. In case you need to sass things up and on a budget.
    P.S. Are pearls and sweater sets really out? (:

  2. Tegan — Thanks for the comment! I esp. like the J. Crew tissue tank with sequins. So soft, so easy.
    Beck – Pearls and sweater sets are never out, per se….just never really all that exciting. 🙂
    M – Funny you mention that. I keep trying to justify purchasing one of these…until I remember that I’m pregnant. Sigh.

  3. Hi,Shana 🙂 This my first comment, but I’ve been loving your blog since I first found it about a week ago. These were great style boards! So fun.
    I have a question, though. Why do you say that white pants have to be for date night only? I have 4 children and I’m wearing white cropped pants **as I type this.** With a black tank top. We’re going to the pool in a bout an hour. My youngest child is 3 now, but I wore white cropped pants when he was an infant, too. I always wash my whites in OxiClean and I haven’t had a problem. Just don’t give ’em grape juice on white pants days ;)I also don’t wear my nicest white pants except for date night, but these cropped pants were from New York & Company and were under $40 – I wear them everywhere!
    Liberate the white lovin’ mamas 🙂
    Again, love your posts!
    ~Jacci in Ohio

  4. Jacci – You are my white-jean hero. I might be a tad biased against white jeans for moms…but it’s only jealousy. I seem unable to get through a single day without spilling splattering or wiping things like coffee, paint, mud or cherry juice all over my clothes. If you can rock it, then go for it!
    Kandy – Sigh. Tall gals look especially good in maxi dresses.

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