8 of the Best Dresses for Teachers That are Comfortable + Timelessly Chic

This post: Kristy’s top picks for the BEST dresses for teachers.

Full disclosure: I’m a home educator, which means I can teach in my jammies of I want to. But I don’t! I love dressing well, even if I’m at home with my kids all day.

For three years, I tutored + directed at our Classical Conversations homeschool community, so I quickly learned that a teacher’s clothing needs to be three things:

• comfortable
• easy to wear + wash
• stylish (because who wants to look boring?)

This post is a nod to you amazing teachers… + your wardrobes! xo

Some of the links in this post are affiliate links.  As an ambassador for LTK + Virginia Dare Dress Co, I earn a small commission when you click on these links + make a purchase. Thanks for supporting this site! xo

Best Dresses for Teachers :: Why I Picked These

The pieces I’ve curated for this post are washable, easy to move around in, and universally flattering. All are designed and created by the lovely Rebekah, creator + owner of the Virginia Dare Dress Co brand.

The eight dress styles featured in this post are actually four dresses, in different colors or prints. These timeless looks will take any teacher or professional woman from weekday to weekend, with effortless style.

I’ve also curated inspiration for accessories, shoes, + beauty products to polish off your look. These are all brands I wear + love:

• Sarah Flint, Rothy’s + Soludos (shoes)
• & Other Stories (jewelry + accessories)
• Charlotte Tilbury (makeup)

Important :: Promo Codes!

I can’t tempt you with beautiful, designer styles without offering a way to save some money. Below are exclusive promo codes just for Simply Kristy Lynn readers (don’t worry, I’ll share them again throughout the post):

• KRISTY10 | Saves 10% off your entire order at Virginia Dare Dress Co
• SARAHFLINT-BAKRISTYL | Saves $50 off your first pair of Sarah Flint shoes
• CLICK HERE (no code required) to save $20 off your first pair of Rothy’s
• CLICK HERE (no code required) to save $15 off your first pair of Soludos

Ready to shop?

Simply click the photos + links in this post. Enjoy these timeless styles!

#1. Samantha Wrap Dress in “Sky Blue”

This gorgeous window-pane wrap dress is fully functional + decidedly feminine! The linen-cotton blend is a huge plus, especially if you live in a warm climate. The neckline is completely modest, but you can always wear a Halftee under the dress for extra coverage.

Polish off your look with a delicate nude theme to complement the airy feel of the dress: these wedge espadrilles (Soludos), pretty matching “rhinestone chain drop” earrings + bracelet (& Other Stories), and a touch of lipstick in “muted apricot” (Charlotte Tilbury).

CLICK HERE (no code required) to save $15 off your first pair of Soludos.

KRISTY10 | Saves 10% off your entire order at Virginia Dare Dress Co.

#2. Samantha Wrap Dress in “Navy Blue”

Change things up a bit with the same dress, just in a darker shade. The Samantha Wrap Dress makes a stunning statement in navy blue!

Stick with the deep maritime vibe and polish off your look with these points in “deep ocean” (Rothy’s), beautiful glass droplet hoops (& Other Stories), and just a hint of “rosewood” lipstick (Charlotte Tilbury).

CLICK HERE (no code required) to save $20 off your first pair of Rothy’s.

KRISTY10 | Saves 10% off your entire order at Virginia Dare Dress Co.

#3. Chloe A-Line Dress in “black”

Buttery soft, legging-like material makes this A-line, pullover dress a weekday must-have. But don’t let the easy style fool you: it’s as flattering as it is comfortable! I own this dress in “periwinkle” (shown below); it drapes beautifully and is easily dressed up or down.

Let’s embrace a preppy look with this blazer (& Other Stories), these timeless sling-back flats (Sarah Flint), and a layered statement necklace (& Other Stories).

SARAHFLINT-BAKRISTYL | Saves $50 off your first pair of Sarah Flint shoes

KRISTY10 | Saves 10% off your entire order at Virginia Dare Dress Co.

#4. Chloe A-line Dress in “periwinkle”

This pretty pullover is just the right amount of classy + comfy! Shown here in dreamy “periwinkle,” it’s a subtle nod to the summery days no one is quite ready to leave behind.

For a relaxed work look, pair it with these Venetian leather mules (Soludos), recycled brass pendant earrings (& Other Stories), a small leather tote (& Other Stories). This dress also styles well with the leather Obi wrap belt, from Virginia Dare Dress Co.

CLICK HERE (no code required) to save $15 off your first pair of Soludos.

KRISTY10 | Saves 10% off your entire order at Virginia Dare Dress Co.

#5. Emma A-line Dress in “Admiral Blue”

A bit more elevated than her sister-style, the Chloe, the Emma dress is made from the same legging-soft material but features a hidden zipper in the back and a preppy half sleeve. This lovely piece was my first introduction to the Virginia Dare Dress Co; the deep blue shade makes its own statement!

Take it to the next level with this preppy blazer (& Other Stories) + a pair of rhinestone statement earrings (& Other Stories). Finish off the look with a pair of leather booties- these Perfect Zip leather booties (Sarah Flint) are definitely an investment piece. You can go for the same look with something more affordable- the Fulton Bootie in black suede (Soludos).

SARAHFLINT-BAKRISTYL | Saves $50 off your first pair of Sarah Flint shoes

CLICK HERE (no code required) to save $15 off your first pair of Soludos.

KRISTY10 | Saves 10% off your entire order at Virginia Dare Dress Co.

#6. Emma A-line Dress in “burgundy”

The Emma is back in a lovely autumnal “burgundy.” The rich hues and figure-flattering cut of this dress will take you from weekday to weekend, in comfort and style.

Dress it up a bit with these points (Rothy’s) in “desert cat” + a pair of recycled brass mini hoops (& Other Stories). Want to really make a statement? Dab on some bold color with this “wine” lipstick (Charlotte Tilbury).

CLICK HERE (no code required) to save $20 off your first pair of Rothy’s.

KRISTY10 | Saves 10% off your entire order at Virginia Dare Dress Co.

#7. Lily Sheath Dress in “eggplant gray”

What could possibly be more timeless than a sheath dress? Featuring a wide boat neckline and flattering waist, tempered with an easy pullover style, the Lily brings the best of both elegance + comfort.

Style the lovely “gray” Lily with these chic dotted tights (& Other Stories), Venetian suede booties (Soludos), + ruched headband (& Other Stories).

CLICK HERE (no code required) to save $15 off your first pair of Soludos.

KRISTY10 | Saves 10% off your entire order at Virginia Dare Dress Co.

#7. Lily Sheath Dress in “olive green”

Lily is back again, this time in a gently muted, autumnal green.

Style this beauty with a lovely ribbed cashmere scarf and matching beanie (& Other Stories), stone pendant hoops (& Other Stories), and this “pop of pink” lipstick (Charlotte Tilbury).

Want a luxury investment piece to elevate your style? The Perfect Stretch Boot (Sarah Flint) in “taupe” suede will take you through fall + winter with unrivaled class. Honestly? I think they pair beautifully with every dress in this post.

SARAHFLINT-BAKRISTYL | Saves $50 off your first pair of Sarah Flint shoes

KRISTY10 | Saves 10% off your entire order at Virginia Dare Dress Co.

Your turn.

In your opinion, what makes a dress “timeless?” Share your thoughts in the comments below.