Welcome to the Weekend: Flattering Colors

Happy Saturday ladies. This week has felt very long yet I’m not happy to see it end. My daughter only has a few more days with us before she heads home and I’ll be sad to see her go. Our visits are never long enough which always leaves me wishing we lived closer.

I’m happy to report that I’m following thru on several Jennifer Connolly of A Well Styled Life wearing Soft SurroundingsI met one of my closest friends for coffee yesterday. Mr. AWSL and I snagged outfit photo’s before I met her and I’m glad I tossed my hat into the car because we ended up sitting outside at Starbucks. Jennifer Connolly of A Well Styled Life wearing Soft Surroundings vest

I love the ease of black hats because they coordinate with everything but they also make the shadows under my eyes look darker. Not my favorite look.Jennifer Connolly of A Well Styled Life wearing

This vest is in one of my favorite (because it’s flattering) colors but you can see, the undereye shadows were still pretty evident.

Jennifer Connolly of A Well Styled Life wearing Soft Surroundings
VEST on sale | BLOUSE on sale | PANTSSHOULDER BAG on sale

I loved how the teal coordinated with my $6 aqua tassel earrings. I debated buying them, which my girlfriend teased me about because they’re one of my favorite colors and… $6.

Jennifer Connolly of A Well Styled Life
BOOTS similar | PANTS | BLOUSE | HAT similar | VEST on sale | SHOULDER BAG on sale

I didn’t order this vest in the petite version, and I should have. The proportion is too long for me, especially with knee-high boots. It would look better worn with shoes but would still be more flattering if it were 4 inches shorter.

Jennifer Connolly of A well Styled Life wearing Talbots blouse

I’m not a huge fan of overly feminine fashion but I love the cuff detail of this blouse. It’s pleated cuffs feel crisp and feminine at the same time.

I’m often asked what to do about hat hair. Leave your hat on! Women aren’t expected to remove their hats the way men are, so unless you’re in a movie theater, leave your hat on.

I’ve had several readers say they can’t get away with wearing a hat?

What about you? Please share why or why not in the comments below.

Thanks for reading and have a great day!


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  1. I think you have a rather swashbuckling look! That vest and the boots are really cute on you and the sleeves of the blouse almost made me think musketeer!! I really like the boots but booties wood be very nice too. The boots give the look ‘edge’ it might look a little school girl with flats or pumps. Just my two cents;)
    Oh hats!! I laughed when I read the reader comment about what do the girls up north do? Honey when it’s -33 degrees your hair is the least of your worries and you wear a tuque or toque that covers your ears and forehead UNDER your parka hood!! Nobody here has good hair this time of year!!

    1. Wowza that’s cold Alison!! I ageee in those temps I wouldn’t care what my hair looked like. Thanks for being here Allison, I always love your contributions to our conversation. Happy New Year!

  2. It’s so hard when your children leave to go home. I understand. Funny how we judge ourselves. I would never have noticed the dark circles. I had to go back and look. You’re way too critical. Of course, I’m the same way. The length of the vest looks just right. But then again, what do I know. Hats? It’s a rare hat that looks good on me. I also hate “hat hair.” Happy New Year!

  3. What shadows under your eyes? I can’t see them — love the vest, btw.

    1. Lol Cynthia! I need to see the world through your rose colored glasses:) xo

  4. OH YES!!!!!!!
    HATS HATS HATS……….especially in SUMMER!!!!!!!
    WE will rendezvous then!!!!!!!!
    I NEED a daughter!!!!!!!

  5. Kathleen O'Brien says:

    I think the outfit is very flattering on you! I chuckle about the earrings, I’ve done that too, debated over something that was a minimal expenditure but I’ve kicked myself later by not getting it!
    I love the hat! I’ve been wearing hats a bit lately, and every time, two or three folks, not just ladies, comment on how they love the hat. Ladies have come up to me on the street and started conversations about how they have hats and never worn them and now they are going to look at them again! It’s amazing that a hat causes so much interest! I’ve quite a collection but have been only wearing them recently as it’s so cold and my hair is short and not covering my ears and they are freezing! But once you’ve got the hat on, you’ve got to commit to the hat and that’s that!

    1. I hear that about hats too!! The stores sell them but few ladies seem to wear them. I agree about keeping them on!

  6. I love hats from bobble hats to berets. Howver my favourites are Fedoras very similar to the one you are wearing. I find them very flattering and they help to finish an outfit.

  7. Kathy Lucas says:

    Would you consider a tour of your closet and how you store your clothes. Whenever you buy new clothes, shoes and boots I wonder how you put them away.
    I always enjoy your posts.

    1. I have a very small closet. That’s a great idea for a post, Kathy. I do keep my jewelry and handbags in an antique armoire so that frees up space in the closet. My shoes and boots are stacked in their original boxes. Out of season shoes and boots are stacked above the clothes, all the way to the ceiling and hat boxes are up there too.

  8. Elaine Thomas says:

    Jennifer, I have loved the hat since the first time I saw you wear it. I wear hats often and usually always get compliments but I never see other ladies wearing them. Go figure. The problem I have is wearing high boots. Although I am a young 71, I feel they look too young for me. Love the vest and I think the length is fine. Especially if the weather is cooler. Happy New Year! Elaine

    1. I seldom see ladies wearing hats either, which always surprises me because they sell so many! It just takes the simple act of putting it on as you go out the door. If the boots don’t feel right to you, you’re wise to avoid them. Personally, I don’t see them as a young person’s look, but you have to wear what makes you feel best Elaine.

  9. I’ve long given up buying anything that I see NOT petite size, being a smidge under 5’ refular sizing just overwhelms me in every direction. That vest looks very cozy and I bet you were the best dressed person on the patio. Happy New Year.

    1. At under 5 foot, you would have to have petite, that’s wise of you. I am borderline at 5’4″ so can go either way with many things. Happy New Year Cyndi!

  10. Hi Jennifer, I am like Linda I like the length of the vest of course that could be because its unbearably cold here. I like the longer vest for their warmth. I am one of those women who doesn’t look the best in hats. I have bangs plus I wear glasses so when I put a hat on I all but disappear under it. My husband tells me its just my attitude that I just need to wear it like I mean it. Whatever that means. lol However since its so cold I just may do it!

    1. Bangs are a problem with hats. I swipe mine to the side before I put my hat on. Bangs poking out under the brim seems choppy to me, especially with glasses. Give that a try and let me know if you like that better. Wearing a hat does take attitude plus gives one attitude…so go for it!!

  11. Jennifer you look so pretty in that vest and your lipstick color is a beautiful contrast. I have been wearing hats more often these days to protect from the sun, but I sometimes find them bothersome. Wishing you a very happy and healthy new year!

    1. Thanks Karen, I am really liking the red lipstick. Hats and parasols are the very best protection. Happy New Year to you!

  12. I really like the vest on you with boots and hat!! Maybe try having the vest shortened a bit if you’d like it better. You could try booties as well. I think you look great though!!

    1. I was thinking booties too! I could shorten it and may try with needle and thread. Thanks Karen.

  13. I agree with Linda about the petite length. I too, and a petite (5’2″) and sometimes I prefer things a bit longer. It really just depends. The blue vest looked very nice, even in the regular length.

    1. Thanks Elaine. I think I’ll like it better without the knee boots too:)

  14. I love hats and have a wonderful collection, yet never think to wear them. Silly, I know. I agree with the best being long with the boots. I would keep the length and go with different shoes.

    1. I agree it’s hard to remember if you have a collection. I store my favorites close to the door but frequently plan the hat when I decide what to wear. Agree on the shoes too!

  15. Jennifer, you look lovely in these pictures! It is true what they say about we are our own harshest critic. My sister, who is my best friend, lives 4 hours from me so I understand how you feel about precious time with your daughter. I love wearing hats and being very fair skinned in the South try to do it whenever I’m outside. But the whole hat head issue is a problem…hairspray, heat, and humidity = glued down hair! What do ladies up in the really cold parts of the country do?? I discovered a milliner back in my family tree which may explain my love of hats!

    1. Thanks, Roxanne! I agree, the hairspray does make for a matted down mop. I thought it was a great outfit but wanted to point out improvements I could make the next time I wore this outfit. I do this intentionally to help everyone look objectively at their pairings.

  16. Perhaps petite would have been a better length but I wouldn’t have thought of it unless you mentioned it because the whole outfit looks great as is. I do see the shadows beneath your eyes because of the hat but again, only because you mentioned it because my eyes are drawn to the vest and the hat. That’s not a deal breaker for me. I do have trouble finding hats that flatter my round head but I have a few and wear them more than ever these days from spring to fall.

    1. I didn’t notice the shadows or proportion while I was wearing it and found it illuminating to see the pictures:) Do you mean you have a round face Janet? Aren’t hats fun?

  17. Jennifer, just my opinion (two cents) but I think the longer vest looks very nice on you and the color is great. I do like hats too. My favorite is a blue one I found in Cambria on a vacation.

    1. It’s funny because it never occurred to me to order the petite version! I liked how I felt wearing it, but these pictures are what made me decide to looked too long. Partially because of the knee height boots. Aren’t hats fun Linda? I love them.

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