For if you’re waiting for the right occasion
Don’t save the dress for somebody’s wedding or a future gala you’re probably never going to. Don’t wait for the trip to Paris. Wear it now.
Today’s the occasion.

via Pinterest
He got some hate for it, but Transportation Secretary Sean Duffy wasn’t being that unreasonable when late last year he encouraged Americans to dress better in hopes of behaving better…well, at the airport, because, yeah, the Transportation Secretary thing (to be fair, he’s staying in his lane).
I don’t really blame us, though. The stuff we find in shops is usually made as if practicality and comfort are mutually exclusive to thoughtful, beautiful design. So, when we put on something out of the ordinary, we can feel as if we’re standing out and not in a good way.

Good news for brands—boring plastic clothes are perfect for bottom lines. Less style and complication means less money spent on artistry and quality materials. Sure, the things we buy are cheaper. (Are they really, though, if we’re not satisfied and keep buying new stuff in hopes that we’ll feel different?)

sportswear from the 1930s

a men’s coat from the 1940s
What’s considered dressy now would’ve been deemed standard day wear in the past.
People had fewer clothes but wore nicer outfits to go to the grocery store, to hang out with friends, certainly to travel.

War couldn’t stop style either. The shoes above are called galesh, first invented for cavalrymen in Persia in the 10th century and recognized as the earliest high-heeled shoes. Heels were meant to keep the soldiers’ feet from slipping out of their saddle stirrups as they rode on horseback (practicality). The pair above is from the 17th century and made with horse leather…dyed with mustard seeds!! (thoughtful, beautiful design).

Thoughtful design was the norm, given that technology and synthetic materials hadn’t yet replaced it at scale.
Convenience and beauty weren’t strangers.
Every day was the occasion.
And it wasn’t just one body type that was considered worthy of dressing up either.
For if you think you don’t have the right body
It’s absolutely possible for any body type to look flattering in clothes. Tall and skinny. Short and round. All the extremes and everything in between.

pics I took at a Marie Claire photoshoot, during my short-lived career as a stylist's assistant
Someone once told me they couldn’t wear cute dresses to go out because then the shape of their belly would show.
???
Okay.
We’ve been brainwashed to the point of thinking only models can look really good in clothes. However, I’ve been behind the scenes at runway shows and at a magazine photoshoot and know that even lanky ladies can look awkward in clothes if the fit’s not right. Last-minute altering and safety-pinning weren’t uncommon.
If you find something you like and if it’s within your budget, invest in getting it altered by a professional.
If not, be ruthless about how things fit when you try them on at the store. Always leave the fitting room to walk around in clothes and make sure the fabric doesn’t ride up or sag in weird places. Know your measurements. Try another size, try another shop.
If it’s not working, you have the right body. It’s just not the right piece.
—Wait, did somebody say it’s not the right time?—
Perfect. Let’s talk about that.
For if you’re not a morning person
You’ve only just gotten up. The brain’s still loading and you’re probably running late for something.
Oh great, now you gotta put on clothes.
Sage advice dictates that you pick out an outfit (and perhaps a backup) the night before.
But a number of factors can make you second-guess pre-selected outfits the next morning. Unexpected weather. A change of plans. Your mood.

Rabessa Ayubi bob hat
More than having just a couple outfits picked out the night before, create several go-to template looks—for example, slacks, button-up, flats, jacket…repeat—that work for a number of occasions and weather conditions.
If you’re still not feeling an outfit, try switching out accessories, shoes, or outerwear.
Think of them less as fixed outfits and more as formulas you can slightly adjust depending on the day.
Hang these outfits up in your closet and set them aside especially for mornings when you really don’t have time (or the energy) to decide what to wear.
If you want to get really organized about it, you can even stick a label on the hanger or on one piece of each outfit, indicating which contingency they’re for.

pics I took during my shorter-lived career as a wannabe street style photographer :)

Here’s the trick—none of these looks should include workout clothes or sneakers.
Wear a fun hat in place of a regular beanie. Put on something leather! or something with fur.

(I did it this past winter and realized how a show-stopper jacket can make up for basic, cold-weather clothes underneath.)
Switch out leggings for comfortable, fitted slacks and sneakers for flats or low-heeled shoes.
Little by little, try a higher heel until you reach the moon. I kid, but switching out something casual for something a little bit more elevated each time works our chic muscle memory until getting “dressed up” isn’t just for special occasions but a daily habit.
