Hi Belle,

I’m starting to see the benefit of wearing more dresses to work and on travel. However, my dress selection is in desperate need of an upgrade. Could you do a post in the near future on a creating a proper dress wardrobe? I seriously need five dresses. Thanks!

Stefanie

Five dresses?  I think I can handle that.  But let’s break it down first.

If I were going to start or rebuild a dress wardrobe for work in the cold weather, I would choose two sheath dresses, one wrap dress, one jersey dress and one sweater dress.

In my opinion, one of the sheath dresses should be a neutral like black, grey or navy, and one should be a color.  For the wrap dress, I would recommend a print.  The jersey dress is the piece you reach for when you’re not feeling your best and you need an easy dress that will be professional, but comfortable.  And for the sweater dress, I would choose a sleek one that can be dressed up or done.

Clear enough?  Maybe a visual-aid will help.

kate spade Darlene Sheath Dress ($398) // Trina Turk Fenella Dress ($298) // DvF New Julian Dress ($365) // Lauren Printed Jersey Dress ($139) // Ann Taylor Colorblocked Sweaterdress ($119)

Black Sheath.  This structured Kate Spade sheath dress could easily be  worn during three seasons.  However, the price is a bit high.  I also found this more relaxed, but classic Jones New York Scarlet Sheath ($119) and this sleeveless Tahari seamed dress for $138.

Plus-size ladies should check out this Tahari Levine wrap-effect dress with a half sleeve.  Petite ladies might like this LOFT textured sheath.

Colored Sheath.  This wine-colored Trina Turk dress is lovely with the pleated details at the shoulder and hip.  I also liked this cobalt Ivy & Blu dress with a 3/4 sleeve and this Felicity & Coco purple and black side-seam, colorblock dress, both under-$150.

Wrap Dress.  This dress is a great choice for lazy days when you have a closet-full of nothing to wear.  If you want a bold print, this Jones New York dress has a blue, grey and white leopard print ($99).  If you prefer solids, Ann Taylor has a lovely belted, wrap dress in twilight blue (also comes in petite).  Plus-size ladies should check out this Land’s End wrap in a blue and green chain print.

Jersey Dress.  Having an easy, jersey dress in your wardrobe that you can dress up or down is a great option.  I like this Lauren dress because the side paneling is really slimming, and the navy color makes it a good choice for multiple seasons.  I also found this inexpensive ruched side dress from Kohl’s and this Donna Rico twist-front jersey dress that comes in a handful of colors.

Sweater Dress.  I like this Ann Taylor sweater dress because it’s fitted but cozy.  It also comes in a gorgeous burgundy and purple colorblock.  If you need something under-$50, I also dig this ultra-soft sweater dress from Target.

Petite readers might like this ruched sweaterdress from Ann Taylor.  For plus-size ladies, I found this simple Mossimo sweater dress, or this colorblock Amy Byer dress.