Style

5 Outfits That Work Every Time

Five Genius Styling Tips from Andrea Linett

We’ve long considered Andrea Linett, the co-founder of Lucky magazine and creator of the site I Want to Be Her, a kind of fashion oracle: she just knows. Her new book, The Cool Factor, reveals the secrets of real-life women, ages 24 to 76, with effortless style. So, what’s the big takeaway? “The most stylish women I know never dress in head-to-toe anything,” Andrea told us. “Great style is all about juxtapositions.” Here, Andrea takes us through five combinations that always look good…

The Cool Factor by Andrea Linett

1. Trench coat + hippie dress: “Bohemian dresses are a great look, but they can skew young and casual, which may not be what you’re going for. If you style one with a tailored trench, you’ve instantly created something sophisticated instead. When putting together an outfit, make sure you’re not creating a costume. A jean jacket over a hippie dress might look like you’re on your way to a festival, but a trench elevates the whole look.” (Try this and this.)

2. Silk blouse + beat-up jeans: “Dressing up jeans with a silk blouse has been a winning combination since the 70s — and it looks just as fresh today. If you do a baggy jean, then choose a more fitted blouse, and vice versa. Also, your blouse need not be fancy: silk is silk, and you can find a great inexpensive blouse that will make you feel dressy in two seconds.” (Try this and these.)

3. Striped shirt + suit jacket: “If you wear a blazer with a silk blouse, you’re doing fine, but it’s kind of traditional. If you go for a striped mariner’s shirt — or a white or grey tee — you’re mixing things up. Put on a pair of leather jeans and you’ve got a forever cool look that’s casual but still very polished. Go for a classic single- or double-breasted menswear style, shove up the sleeves and get comfortable.” (Try this and this. And maybe these.)

4. Pencil skirt + biker jacket: “I can imagine a woman considering a biker jacket and thinking it’s not for her, like, ‘I’m going to look like a character from Grease.’ But she might surprise herself because it’s actually one of the easiest pieces to wear. I like to use it to toughen up things that aren’t tough. A pencil skirt is the perfect partner in crime. It’s sexy but sensible. Pair it with a biker jacket and you’ve got just the right amount of edge.” (Try this and this.)

5. Baggy chinos + pointy-toe pumps: “If you wear chinos with loafers, you’ll look nice and preppy. But put on a great pair of pumps, and there’s instant sex appeal. You’ve basically unlocked the French girl’s je ne sais quoi. When I’m craving a chino pant, I look for one that’s slim, because I’m 5’3″. But if you’re a little taller, you could get away with a loose, vintage mens pair, rolled at the cuff, which looks amazing.” (Try these and these.)

Thanks for the tips, Andrea! We are loving your new book.

Thoughts? Which looks would you most want to wear? You can find many more style tips in The Cool Factor, if you’d like.

P.S. An ode to stripes, and why we’re wearing non-stretch jeans.

(Photos from The Cool Factor by Andrea Linett. Graphic design by Rachel Ball for Cup of Jo. Interview by Lexi Mainland.)

  1. clothing splendid

  2. KIRSTY says...

    I’d love to see some takes on plus size fashion.

    • Jenny says...

      Why wouldn’t the above be consider for all fashion sizes? I think they seem fairly applicable across the spectrum.

  3. I love this outfits! Really getting inspired for warmer weather and to got o uni!
    Love
    Pili

    Records of my Troubles

  4. Such awesome suggestions! The trench and boho dress are an exciting new prospect and the silk blouse and beat up jeans are always a fantastic choice! Thank you for the reminder to not dress in a costume! Sometimes the jean jacket needs to be put down ;)

  5. Leah says...

    I love those jeans. Do you know who makes them? Thanks!

  6. Darcy says...

    Great ideas. Some of those shopping suggestions are mostly sold out.

    I would love ideas on how to pull off a long, floral dress once the trench is gone. Very cute in the picture, but once we get to the office—or restaurant or art gallery or friend’s house—and we take our coats off, how does one not look like she’s in a nightgown? Would love suggestions on this. Anyone? Thanks.

    • Sandra says...

      I was thinking the same thing…if I left a trench on people would keep asking me to take my coat off a stay awhile. :-) Maybe one of those sleeveless belted trenches that are kind of more like a long vest?

    • Justine says...

      I thought the exact thing! Cute when running around and I love me some coats, but …

  7. Becca says...

    Thank you, thank you, thank you! I love fashion and style, but struggle to put together an outfit for myself. This post has helped me to think about how I can rework my wardrobe and create new combinations.

  8. Caitlin says...

    I will always lovingly associate Andrea with Sassy, that to me is her most important claim to fame. She was one of my favorite parts of that magazine. I remember a hysterical photoshoot/piece she did a few times called Dopey Fashion Poses. It was amazing in 1993 or whenever it was and is still completely relevant and irreverent today.

    • lexi says...

      Yes! I’m commenting just to say yay for ANDREA! And Sassy! A whole generation of us imprinted on what individual style meant from her. She is a legend. I remember dopey fashion poses too — one was “the hip dysplasia”?

  9. Natalie T. says...

    I love the dress-up and dress-down combination. Numbers two and three are my favourites but sometimes, I’ll swap out a French striped-T with a t-shirt. I also like wearing my converse with fancy pants.

    Now, I’ll have to pick up this book!

  10. Andrea Linett! She’s always been awesome, way back to the days of Sassy. Love seeing familiar names…

  11. B. says...

    I remember Andrea from her days at Sassy! Long time style influence :)

  12. Timeless, classic basics–versatile and stylish.

  13. Awads says...

    I don’t know about beat up jeans for anyone over, say, 40. I’m 48 and feel totally ridiculous in ripped jeans. It’s like I should be able to afford a new pair if mine are torn, no? Who am i kidding? The biker jacket, on the other hand, is awesome. I bought one at Banana Republic in 1994 and still wear it. It’s an investment piece, for sure!

    • Jill Palumbo says...

      I’m 60 and obsessed with ripped jeans. I don’t know why, I just love them. I am looking forward to my retirement when I can wear them every day! My ex husband and my mother don’t like them on me, but otherwise I get compliments when I wear them, so I don’t feel too bad.

    • Sandra says...

      I’m the same age you are and don’t love ripped jeans for myself anymore either, but I think something that is a faded with a rolled up cuff like the ones in the above pic are really cute.

  14. Kate says...

    Whenever I wear #3, the striped shirt and blazer, my husband calls me Liz Lemon (and not as a compliment). But I always knew Tina Fey was cool – I want to be her!

  15. This is awesome + helpful! I love CoJ’s content so so much. Thank you ladies!

  16. I am not cool enough for a leather jacket nor do I think it’s me, but I do appreciate the juxtaposition. My go to is slouchy jeans + white or striped blouse with flat sandals, chucks or pointy heels! Change the lipstick & when you change the shoe and it works. Ta-da!

    Joanna what do you think of the choker trend being back? would you wear one?

    Xo Lendy
    http://www.twoplusluna.com

  17. I don’t know…head to toe black is always pretty chic! :)

    • Leah says...

      I agree!

    • Charli says...

      Same here! Love head to toe black.

  18. Erin says...

    Love this! Also appreciate the budget-friendly suggestions for the pieces. Thanks!

  19. Aga says...

    Love it! I’m not one to read style books, but this one sounds great! I just placed it on hold at the library. And seeing at how I changed 3 times before heading out the door this morning, it can’t come soon enough!

  20. Samantha says...

    I’ve been wearing number 4 and 5 a lot lately. I got a leather jacket on Black Friday and I’ve been wearing it anytime I go out at night, so I don’t get cold. I usually wear pencil skirts if I’m dressing up and I love the badass vibe that the jacket adds to the outfit. I wear number 5 to work almost everyday, since I got this new job. High heels are almost obligatory, and since I saw the department’s director wearing pointy toe heels when she interviewed me, they seemed like a safe bet, so I got black suede-like material ones. But the pants I wear aren’t exactly baggy since I’m very short (5’0″) and I would look like a hot mess.

    • Joanna Goddard says...

      you sound adorable!

  21. Ceridwen says...

    One of the best things I have done to make my life easier, and myself feel better, is clear out most of my clothes and stick with things I really love. I love that line about creating an “outfit instead of a costume”. Sometimes I have felt like I’m in costume if I’m trying too hard. It seems to take time to see what works for your personality and I love her advice! I’m keen to read her book!

  22. Bobby says...

    I have the book, totally worth buying.

  23. Alice Quin says...

    Love this! Inspired by her quotes and now want to run out and buy some chino pants! :)

  24. I purchased a wonderful moto jacket a couple of years back and watched as it sat in my closet collecting dust. I have a pretty feminine look and just hard a hard time ever feeling like it was ‘me’. After just having my 2nd baby I picked it up one day and wore it over a t-shirt and instantly felt less of a mess, since then it’s been my new staple! I instantly feel elevated and cool rather than the poppy spit up covered mess I am in reality! I love these suggestions!

    Xoxo http://www.touchofcurl.com