There are different fits to maxi dresses and skirts. Some are very billowy and flowing while others have a slimmer fit. The shape of the maxi dress or skirt determines the type of shoe to wear with it and the fit of a top, or topper (jacket, blazer).
Guidelines for your age:
45 +: Monochromatic looks great for you. The neckline determines how much you feel comfortable revealing. Cowl neck maxi dresses are very flattering neckline and usually loose enough to hid any figure flaws in the mid-section. If wanting to show your cleavage a little more and not concerned with the skin at your chest area, go for one color with a deeper front v.
Splendid Cowl Maxi Dress, $138 (Strawberry or Black)
Great dress to add a thin knit long cardigan in white or taupe. Add an animal skin belt over it in taupes and whites with a gold buckle. Wear with a heel or a jeweled flat sandal.
Jessica Hart for Pencey Standard V Neck Maxi Dress, $176
Dolce Vita Cybele Woven Flats, $170
Trina Turk Marisol Halter Dress, $438
30-45: Deep V Necks, High Slits up the thigh, stripes, and patterns all work well. Go for what works with your style personally and professionally. Deep V Neck and Thigh Slits make dresses in appropriate for most corporate work environments, creative fields can still work this look.
Wear this dress with a flat but metallic sandals for day. Add large gold cuff and large gold statement earrings.
BCBG Meadows Maxi Dress, $198
Dolce Vita Bagley T Strap Sandals, $170
For work wear this dress with a fitted cropped black blazer or a light knit long black or blue cardigan and coordinating colored heels. At night try a stappy sandal and and bold jewelry.
Charlie Jade Madison Maxi Dress, $196 ($182 at South Moon Under)
MM Couture Strapless Printed Ruffle Maxi Dress, $98
Under 30: Go with flirty designs and prints. Wear for casual days on the weekends or go dressier for work or at night. The key to wearing this at work is to wear a blazer or sweater with it to look more professional. Avoid crazy prints when at work, unless you are in a creative field (magazine, design, styling, etc.).
Top Shop Floral Mesh Back Maxi Dress, $92
Saint Grace Santa Fe Noa Maxi Tank Dress, $145
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