- Monteau Top via Marshall’s (Similar by Vintage Havana)
- Old Navy The Diva Jeans
- Target Sandals (Similar by Deena & Ozzy)
- Cuyana Tote
I think I found some really fun dresses for you!
First is this pretty b&w dress from H&M ($59.95). It has a shorter v-neck, but you’ll be able to wear a regular bra with it. This would look adorable with a pair of cute sandals and a messy ponytail. It’s got some volume through the skirt to help with tummy concealment.
If you want something more vacation-y, this Tommy Bahama dress ($67 from $148) is somewhere between a caftan and an actual dress. I love the embroidery. This TWO by Vince Camuto dress feels similar ($59.99 from $99). It’s a little casual and a little dressy and that skirt is great! You could wear it with sandals or wedges. The drawstring waist is flattering.
For maxi dresses, I’m a big fan of this one from Target (I own it in a different color). It’s marked down to $21. It’s not too low cut and it’s very stretchy and comfortable. A more casual maxi dress option is this white C&C California slub jersey racerback maxi ($42 from $98). You could wear it with a sports bra! It would look awesome with gold or cognac sandals.
ASOS has some really good options. I love this scuba fabric tie-dye shift dress ($67.71). This simple shift dress ($48) would need to be worn with a strapless bra, but I like the higher neck. How pretty is this white dress with pique trim? It’s $73. This asymmetric hem dress is marked down to $36 (from $73). The taupe color would look so good with silver sandals. If you liked the trendy shark fin hem, this shift dress (on sale for $56 from $81) would be cute.
Have fun on your vacation!
Let’s start with heels. I’m not sure if you need to wear them, but it’s never a bad idea to have a pair of go-to black heels that you can stand in for a really long time without your feet being torn to shreds. It’s can be hard to find affordable heels designed for comfort that aren’t clunky and terrible, but Miz Mooz has a decent selection. These basic black pointed-toe heels are marked down to $45 from $110. If you want a pair that’s a bit more fun, I’m loving these ones ($45 from $110). There are additional sizes available at DSW for $70. Tsubo shoes also get great reviews for being very comfortable and walkable. These D’Orsay black pumps are $130. Another good brand to check is Anne Klein. They’re often discounted and get high marks for comfort. This black heel is $69. If you like a shorter heel, try this pair instead ($79). This ankle strap pump ($79) is adorable and is also available in a pretty great taupe color. I think this white pair (marked down to about $35) is really chic. If you can find Donald J Pliner shoes on sale (this pair in a size 6 is $102 from $228), they would work great for you.
The other option for you is a wedge heel/sandal or wedge boot. It’s hard to find an uncomfortable wedge shoe. Wedges also look good with cropped pants. If you can go more casual, TOMS natural wedges ($69) will go with everything. If you want a pair that’s more fall-friendly, check these out instead ($69). I’m also a HUGE fan of Aerosoles wedges. I have a couple pairs I’ve owned for years. And I mean YEARS. (One pair since college!) They are the most comfortable heels I own. You have to do some searching to get past the clunkers, but once you have those little clouds of delight on your feet, you’ll be glad you took the time to hunt. Their basic wedge heel is $23-$99 (depending on which of the dozen colors you like). These ($69) feel more summery, but you could get at least 2 more months wear out of them. If you want more of an ankle boot style, check these out! They’re $89. Love the taupe color. You could also do a low wedge pump, like these from MICHAEL Michael Kors ($145). Rockport makes a great gray wedge for $140. Donald J Pliner has a black pair (in size 7 and 8) marked down to $132 from $198.
As far as flats, I have two brands to recommend: Yosi Samra and Dolce Vita/DV by Dolce Vita. I’ve found all my Dolce Vita shoes to be very comfortable and they have more trendy flats styles available, like these chic pointed toe loafers ($90). I love these D’Orsay style flats too ($79). Anthro marked down a pair of loafers to $103. Yosi Samra flats are awesome. They’re so comfortable and made in lots of colors/styles now. A basic black pair ($66) is a good idea, but I love these fun snakeskin ones ($70). They also make a great smoking slipper style (about $90). I like those with ankle-length pants. Also worth noting are Seychelles shoes (don’t forget to check out their wedges too). This is a perfect pointed toe flat ($90). These mini-wedge flats are cute ($63 from $85).
I hope this helps and good luck with your new job! :)