Fashion Inspired by Slate's Dear Prudence aka Investment(ish) Clothing For Fall

I’m a huge fan of Slate’s Dear Prudence column. While I don’t always agree with Mallory Ortberg's option, I always look forward to reading it. Last week, this question really got me thinking… 

I want to give the letter writer a hug and offer her a cocktail. Not only was her new bag destroyed (seriously the worst), but she also has to be reminded of this awful incident every time she encounters the most inconsiderate coworker in the world.

One argument I noticed came up in the comments was whether $200 was a lot for a handbag. After really thinking about it, I’ve concluded it’s only fair to say that it totally depends on the person and the handbag. $200 might be a steal for some, but a splurge for others.

Sometimes, it’s challenging to write roundups both for this blog and all of the other websites I’ve written for in the past. It’s always been my personal policy to feature products that work for a variety of budgets. There are two reasons for this. The first is that you don’t need to spend a lot of money to have style. The second reason is that it sucks when nothing is in your reach. I don’t want anyone to read my blog and feel badly about themselves. I’m all about being aspirational, but overly aspirational just isn’t my niche.

However, while fast fashion has it’s place, I am a big proponent of spending a little more to buy quality clothing you’ll want to wear for more than one season aka investment(ish) pieces. Here are some of my favorites for the fall. 

Honkey Tonk Skirt by Draper James

Draper James’ Honky Tonk Striped Skirt is timeless and versatile. Wear it to work with a white button down, a sexy top on date night or with a t-shirt to brunch. At $215, this is one of those bold pieces you can wear just about any place.

I love Draper James. Created by one of my favorite actresses, Reese Witherspoon, the brand is all about curated southern charm that stands out whether you are in Dallas or Detroit.

Chantal Faux Fur Cropped Vest by N:PHILANTHROPY

N:PHILANTHROPY’S Chantal Faux Fur Cropped Vest puts the “vest” in “investment(ish).” . If you’re not a vest person (no judgments here), but like the look, check out the Georgie Faux Fur Cropped Jacket instead. Both are 100% cruelty and guilt free because N:PHILANTHROPY donates 10% of their net proceeds to Children’s Hospital of Los Angeles and the SPCA of Los Angeles.

Alana Cropped Distressed High-Rise Skinny Jeans by J. Brand

For $240, J Brand’s Alana cropped distressed high-rise skinny jeans are the happy medium of being distressed. Finding distressed jeans has been a challenge for me. Jeans that are not distressed enough look I'm wearing something that needs to be thrown out and overly distressed jeans look like I'm trying too hard. 

Luke Lace-Up Blazer by Intermix

For $425 with unique raw edges, Intermix's Luke Lace-Up Blazer is more badass than business. It’s the perfect blazer to wear with your J Brands or with leggings and boots.

Split-Side Wool and Cashmere-Blend Midi Dress by T by Alexander Wang

If you’re missing your summer maxi-dresses, T By Alexander Wang has your fix for fall. Their wool and cashmere blend midi dress is equally comfortable and stylish. For $345, you’ll be able to wear it through the winter with warm leggings.

Meridian Cashmere Wrap by Lilly Pulitzer

This $198 Lilly Pulitzer cashmere poncho does two things. It keeps you warm without being heavy and it adds a fun pop of color to your ensemble. Seriously, if you are one of those people who wears all-black a lot, you need this poncho like water. 

Trista Dress by Trina Turk

If you like Missoni, but also paying your rent, check out Trina Turk’s Trista dress. It’s a really useful fall piece for those of us who live in warmer climates. It’s currently on sale for $283.50 but normally costs $378. 

Adalyn Long Sleeved Blouse by Equipment

If there is one item I think is absolutely essential to spend more money on, it’s a white button down shirt. French label Equipment has built their popularity this type of shirt. While Equipment’s signature style is somewhat menswear inspired, their the Adalyn Long Sleeved blouse has softer lines and is worth every penny of $218.

Laverne Asymmetrical Dress by Alice + Olivia

You need a black dress for forever and the Laverne Asymmetrical Dress from Alice + Olivia is such a keeper. (I seriously want it for myself.) While the asymmetrical look is super trendy right now, this dress is so something you could wear to every wedding and event you ever attend for the rest of your life. I mean you wouldn’t, but you could…