I’m a good person to write this essay as I more often than not fail at looking my best. But I study fashion, try to improve my look because quite frankly it’s important to me, I enjoy it. I think of dressing oneself as artistry and marketing combined, a chance to show off your personality and creativity. I’ve learned lots of tricks along the way. When you get it right, people notice and often comment. When you get it wrong — crickets.
l. Get rid of 1/2 your clothes (less is more)
Half the clothes in your closet don’t look great on you (I’m betting). If you get rid of them you will never put them on. When I worked at Simon and Schuster in the ‘80s, the best dressed employee was Melitta Susmann, the Art Director. She always told us she had the smallest amount of clothes in her closet. But she’d walk in with a skirt, jacket, pumps and scarf and look like a million bucks (which was a lot back then) and never seemed to repeat outfits. Still can’t figure it out.
2. Review your old photos (where did I get it right)
The other day I saw a picture of me, one of the best ever taken. Why I asked? Yes I was super tan, but I had a tight navy cashmere sweater, white pants, a pearl necklace and earrings, and this blue and white striped headband. Luckily I still own all, as I have a habit of given my clothes away too fast. I wore a muted purple eye shadow which made my eyes look super green (I know purple makes green eyes pop). Today I’m wearing it again and feel great. Sometimes you need to review the past to look good in the present. Nothing is really new under the sun when it comes to what you looked best in. Resist joining new clothing fads that don’t suit you, instead just add new versions of what always worked in your wardrobe. But by all means add a pair of black Palazzo pants, even if you never had them.
3. Copy looks you like (fashion magazines, Instagram)
I play “I can do that” when I see an ad or post that includes things I own. Also known as “who wore it best” I put on an outfit I have that almost identically mirrors the picture I see and love. Somehow it’s hard to see outfits in your closet, but easy to see them in a picture, and often you own all the pieces, or something very similar. Copy and Paste dressing.
4. Make the man (or woman in this case)
Before you put on a single clothing item, lay it all out. My kids in Kindergarten would “make the man” where they laid the clothes out the night before on the floor and then slipped into the clothing man in the morning. Same for us, put out all the clothes you want to wear on your bed and move things around until you love what you see. Add jewelry, scarf, handbag, etc. and make the woman. If you start by putting on one thing and adding and deleting on your body you won’t see the whole picture at once. Just like a fashion designer sketches the whole outfit before sewing, try this for yourself.
5. Know your best fit and your best colors
Often we know what our best colors are. More difficult is to know what style flatters our body (me: 5’3, short waisted, small bust, thus need tailored tops to showcase waist, nothing boxy, and short skirts/dresses to showcase my legs) and yet when we walk into a store all bets are off. We buy what we’d like to dress like vs. sticking to the plan. Buyers regret often follows. Of this I am a professional.
6. Shoes make or break it
Willy Loman in Death of a Salesman knew this. “He’s a man way out there in the blue, riding on a smile and a shoeshine . . . A salesman is got to dream, boy.” You may not need a shoeshine, but the right shoes are essential to making the outfit shine. If you don’t know which shoes are right, look at fashion websites or magazine photo shoots, they spend time getting it right.
7. Jewelry
Check out what news anchor women wear, Kamala Harris, actresses, Tiffany catalogue: chunky gold chains are in, triple layered fine strands and pendants, or no necklace at all. Earrings can be simple minimalist studs or showpieces, but never bold earrings and statement necklaces together competing for attention. In the ‘80s in NYC I went to work in Publishing/Advertising with as much jewelry as there is tinsel on a Christmas Tree, that look is OUT. P.S. Diamonds and pearls never go out of fashion.
8. Hair/Makeup/Glasses
Hair is most important to get right, makeup too. If you don’t know what to do here or still have questions ask your trusted friend, or beautician. Make up tutorials are everywhere on Instagram but first decide how much time you want to spend on each (me: 10 minutes tops makeup and hair). Lately I’ve gone gray (love it), wear long hair mostly unblown pulled into a pony tail. It’s what I like, and it’s me. I don’t like hair in my face. With thick hair I get away with murder. Glasses, if you wear them, they must be right for your face, not the face you see on someone else (if only).
9. Outerwear can make or break your look
I’ve seen people show up to formal weddings wearing down coats, and the dress hanging out a foot longer, especially in Boston, where warmth can trump fashion. Think as carefully about your jacket, sweater, coat as you do about your clothes themselves, especially when you live in a cold climate where no one ever sees what’s under your coat anyway.
10. Accessories matter (like the right handbag)
In Santa Monica where my two nieces live, they always ask me “what’s your handbag?” when I share my outfit I’m going to where. Who thinks of this? Ok, handbags also make the outfit, even in Boston. And here you can be as creative as you want: vintage, status labels, cross body, or fanny pack, like my black Lululemon mini I can't live without.
Have fun!
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