“I know how to dress for the grocery store. I know how to dress for a wedding. I’m at a loss everywhere else.” Does this sound familiar?
A client recently said these exact words to me – and she’s not alone in feeling lost with what to wear. I think it’s a symptom of the last couple of years. What you wore before the pandemic doesn’t make sense for you anymore (your priorities have shifted, your work life has shifted and your body may have shifted). But what you wore for the last two years doesn’t work as you start seeing friends again. Or begin your hybrid office schedule. Or resume your monthly date nights.
So, what can you wear when you don’t know what to wear? I like to think of it in terms of degrees – shifting your look to dressier (or more casual) occasions step by step. So, I’m starting with two separate outfits. One is a super casual look, with tips on taking the same concept and elevating it to something dressier. And the other is a dressy look, with ideas to make the same concept work more casually. So, you’ll finally know what to wear when you’re going someplace that’s dressier than the grocery store – but not as dressy as a wedding.
“I KNOW HOW TO DRESS FOR THE GROCERY STORE”
Jeans, a t-shirt, sneakers and a neutral jacket – one of the simplest outfit formulas. And whether you’re thinking, “that’s exactly what I wear to the grocery store” or “that’s too dressy for my grocery store”, it’s a great basic outfit for a bunch of casual occasions. You can wear this to:
A Target run.
Your kids’ soccer practice.
Running a dozen errands.
When it’s time to step it up, use the same essential outfit formula – just kick it up a notch. Stick with jeans, but trade out your jacket (that one that you keep in the back seat of your car) for a casual blazer or nice cardigan. Elevate your t-shirt to something that’s more of a top (read this for other casual top ideas). Slip out of your sneakers and into a flat mule. And while you’re at it, throw on some simple jewelry. This outfit works for:
Lunch with friends.
Your business casual office.
The last PTA meeting of the year.
STYLE TIP: When you’re looking to elevate your outfit, structured pieces can add that extra polish. A cardigan is dressier than a hoodie. A blazer is dressier than a cardigan. A shaped knit top is dressier than a plain t-shirt.
For those days that jeans don’t feel appropriate, it’s time to transition to actual pants (here are my picks for casual pants that aren’t blue jeans). But other than that, the outfit formula doesn’t change much. You can still use the blazer that works with jeans, but go for a silky blouse. Upgrade your jewelry. Try heels if you’re in the mood. And then wear this to:
A formal work presentation.
Dinner with the in-laws.
Those times when you need to dress up, but a dress doesn’t feel right.
STYLE TIP: Another method to make your outfit dressier is by elevating your fabrics. A silk t-shirt is dressier than a cotton one. Straight leg ponte pants are dressier than straight leg jeans. A wool blazer is dressier than a knit one.
“I KNOW HOW TO DRESS FOR A WEDDING”
Dressing for a wedding can feel like a no-brainer because you rarely diverge from this outfit formula: cocktail dress + neutral heels + pretty jewelry (and a wrap if you need it). And if it ain’t broke, don’t fix it. Because this combo works for:
A cocktail party.
Dressy events all the way to black tie.
The fanciest occasion on your calendar this year.
STYLE TIP: Metallic heels, a few pieces of fancy jewelry and a neutral wrap are accessories that can get you through the busiest party season. Because the same ones can work with a bunch of different dresses (click here for a few other dressy pieces to complete your party wardrobe).
When a cocktail dress feels like too much (but pants or jeans don’t feel like enough), take it down a notch with a more casual dress. It can even be the same shape and style and color as your cocktail dress – but in a different fabric. This is another example where fabric choice makes a huge difference between feeling too dressed up and like you picked the perfect outfit. Think about it: a sequin dress feels dressier than a lace one, while a lace one feels dressier than a silk one, while a silk one feels dressier than a cotton one, etc. Wear this outfit to:
A baby shower.
Girls’ night out.
A nice outdoor party.
STYLE TIP: Other things that also contribute to the dressiness of a dress – solids are dressier than prints, dark colors are dressier than light colors, long dresses are dressier than short ones. (These are definitely generalities, but good rules of thumb when you’re trying to navigate dress codes.)
Dresses aren’t only for dressier occasions – there’s no reason you can’t wear one for every day (check this out for my favorite kind of warm weather dress). But when you’re working from home or hanging out with family, a dress that feels more like a t-shirt hits the perfect note. And otherwise, the outfit formula stays the same: dress + neutral shoes + pretty jewelry (and a layer if you need it). You can wear this to:
Sunday brunch at the corner café.
Casual date night.
Just because you’re in the mood.
Did you get any outfit ideas for those in-between occasions? Drop a comment to let me know!
I’ve helped hundreds of clients create outfits that work for every aspect of their lives – including the grocery store, weddings and everything in between. If you’re curious about what it’s like to work with a wardrobe stylist, click here to check out the framework I’ve used with hundreds of clients. And then click here to see what my clients had to say once they completed the process.
