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Is It Better To Be Overdressed Or Underdressed?

Updated April 2019

is it better to be over dressed or under dressed

Is it better to be overdressed or underdressed? My answer: life is an occasion. Dress for it. This means, look your best. Don’t save your nicer garments for parties you never go to and people you’ll never see. Whether you’re heading to the grocery store, having casual drinks with friends, or eating dinner at home with the family, step it up and dress well. I am not saying dress as if you are about to run into your favorite ex-boyfriend at a club. Instead, respect yourself and the company you keep by looking nice. With that said, there are times to be overdressed and times to be underdressed.

Times It is Better to Be Underdressed

1. Walking The Dog

As pictured, it is quite impractical. My canine friend Jesse definitely wanted to go faster than my heels allowed and silk is not conducive to animal paws. Best to stick with jeans, shorts, summer dresses, and other easy-to-wash clothing. This goes for basically all dirty and physical activities, although I can vouch that going to the batting cages in heels can be done.

2. Day Date With A New Fella

Is it better to be overdressed or underdressed for a date? If it’s during the day and he’s kind of new or brand new, look great, but dress casually. Leave the heels and dress at home if you’re not a dress kind of gal. Overdressing will only escalate the uncomfortable feeling for both of you. He will either judge you for the high effort or it will make him feel guilty for being too casual.

3.  Outings With A Male Co-Worker Or Friend’s Husband

No need to send mixed signals to men you don’t need attention from. Unless you are always fabulous, hold back on the over-effort when specifically hanging out with these sorts of fellas.


Times It Is Better To Be Overdressed

1. Dinner Out

Use this as an excuse to dress up. It doesn’t matter where you are going, enjoy the evening out in your favorite dress or heels.

2. Having People Over

This is your house. It is absolutely the perfect opportunity to take your look wherever you want. If you feel self conscious about being the only one well-dressed, prepare your guests for your attire and request they join in on the theme.

3. Job Interview

Unless explicitly instructed, or you are sure the tone of the company or industry would find it inappropriate, go for a suit instead of business casual. The sophistication of your outfit will show respect and your serious interest in the position.

4. Drinks Out

I repeat: use this as an excuse to dress up. It doesn’t matter where you are going, enjoy the evening out in your favorite dress or heels.

5. Lunch With Your Best Friend

She loves you! Make a plan to get dressy and grab those sandwiches or sushi.

6. Holidays

There is no need to stay in your pajamas for Christmas. Show your festivity by throwing on a great dress.

7. Cocktail Parties

If the party on Saturday has the word cocktail in front of it, grab your most fabulous outfit and display your good taste. Just hold back on the floor length gown. Save that for the formal wedding, Oscar party, or when you have people over.

8. Party Or Event

If the occasion came with an invitation, time to bring out a stunning outfit. I dare you.

So, is it better to be overdressed or underdressed? As you can tell, there are far more occasions and reasons to dress up than to dress down. The only time you want to dress down is when showing too much effort could damage a relationship or your clothing.

fashion-blog-san-diegostylish-woman-walking-dogis it better to be overdressed or underdressed

Photos by Dayley Photography

(No animals were harmed during the production of these photos, although that cannot be said of the dress.)

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