Classic Style
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What You’re Shopping For: Dresses for Everyday + Work.

By: Jen Shoop

*Image via Co.

This WYSF is taking a slightly different tack. I received a number of questions about everyday dresses for work and daily life and thought I’d do a deeper dive into this subject. For me, the markers of a good everyday dress are as follows:

  • Does not require adjustment/fidgeting/tugging throughout the day
  • Is modest — by this I mean I mean I do not want to be worrying about flashing too much of yourself, bearing too much cleavage, pulling up a collar, tugging at a hemline while chasing children, in an interview or at a meeting, chatting with their teachers/friends’ parents, catching up with neighbors, etc.
  • Is comfortable — both in material and fit
  • Works well with bras
  • Makes me feel pulled-together
  • Has a little extra pizzazz that makes me excited to wear the piece
  • Is flattering — I need definition at the waist and prefer a midi length
  • Is versatile — personally, I love pattern mixing and matching so I will treat some patterns (especially stripes/ginghams) as “solids” but the safest bet is to find a solid colored dress in a classic fit that you can re-style a million ways with different layers, footwear, scarves, etc.

Below, a few great buys for everyday style. Most of these will work whether you are in an office or working from home or caring for children (so, also working from home). One note re: versatility — literally any of these dresses could be paired with any of the shoes/bags featured, with the possible exception of the samba sneakers (which I personally wouldn’t pair with the peter pan collar dress, for example). But basically, they are all neutral classics that play nicely together.

CLASSIC EVERYDAY DRESSES

01. CO SHIRTDRESS — This is the most expensive piece in the set, but I’ve eyed it for years now. Just a classic, timeless piece that you can lean on for decades to come. Pair with pearls for an important meeting or with Sambas for the farmer’s market.

02. PRADA TOTE

03. TORY BURCH SWEATER DRESS

04. AEYDE SLINGBACKS — These have a fashion-forward minimalism reminiscent of Celine.

05. GAP PUFF SLEEVE SHIRTDRESS

06. CLUB MONACO MELISSAH DRESS — The tone-on-tone belt with this elevates the look considerably.

07. EMERSON FRY DRESS — Longtime readers will recognize this dress, which I own and adore. It is so flattering (long, lean lines, with a self-cinch waist).

08. LOEFFLER RANDALL BALLET FLAT

09. CAPTOE SLINGBACKS — Chanel vibes. Have it on good authority from Nan Philip that these are a good buy — surprisingly well-made for the price.

10. SAVETTE POCHETTE — I have been loving these long, flat bags coming out this season. This one is ultra-elegant with the gold clasp.

11. J. MCLAUGHLIN MAKENNA DRESS — I love everything about it. The belt, the drop-waist, the collar, the color. It is currently somehow on sale for under $70.

12. TODS TOTE — A timeless thing of beauty. You can get the look for much less with this style.

13. SEA SMOCKED LONG-SLEEVED DRESS

14. BANANA REPUBLIC DENIM UTILITY DRESS — Layer over a patterned turtleneck to switch things up.

15. LOEFFLER WOVEN BALLET FLAT — Bottega vibes at a fraction of the price. Love the slightly higher vamp.

16. KHAITE BOOT

17. VAN HOLZHAUSEN SHOPPER

18. GAP DENIM TIERED SHIRTDRESS

19. APIECE PART MIDI DRESS

20. MARGAUX BALLET FLATS

21. SAMBAS

As mentioned above, I love patterns, so I would also elect this Thierry Colson (Tuckernuck has a similar style for a fraction of the price), this Neve and Noor, and any of the Julia Amory shirtdresses as contenders as well.

I am also going to do a handful of really quick hit single answers for other inquiries —

Q: Affordable tennis outfits. Target has a great $28 pleated white tennis skirt.

Q: Pretty vacation dresses for under $75. This Gap dress in the rainbow stripe!

Q: A luxury bag that is not all over the place as a gift to myself for a milestone at work. Congrats! This Loewe.

Q: Classic sneakers for little boys. Keds Graham sneaker. Adorable. Works with jeans, shorts, or jon jons.

Q: A black heel for the wedding guest circuit. Actually perfect.

Q: Rainy day activities for little kids. Spot it!

Q: Easter dress. This skirt and this matching top.

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4 thoughts on “What You’re Shopping For: Dresses for Everyday + Work.

  1. This is really helpful. I also love a good comfy shirt dress. I don’t think a sweater dress would be flattering on my body but I like the idea of them and want to feel warm and snug on cold winter days like today.

    1. I’m so glad you liked this post! I feel the same way about sweater dresses. Love them on other people but every time I try one, it’s either clinging in the wrong places or not clinging in the right ones. I am petite but curvy and so the straight-cut ones that just slide over the body like a sack do me NO favors.

      Maybe one day I’ll find a good one — I was tempted by that Club Monaco one because it has shape to it that might be more flattering for me.

      xx

  2. Which one is the dress in the photo at the top of the post? Thanks.

    Great post, sure it took A LOT of time since these type of dresses are not easy to find.

    1. Thank you, Nancy! The dress at top is from the brand CO but I think it’s an older version of the shirtdress I shared in the collage. You might do some digging on their site to see if you can find the one with the more dramatic sleeves.

      xx

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