Ask Hannah!

There is nothing I love more than planning outfits and shopping. I have chosen the more recently based on staple items and items that can work with multiple outfits. Most of the things I have now would fit into the “office casual” or “office to evening look”. I had not considered outfits and heels for occasions but I LOVE LOVE the idea. What would you recommend for both outfits and shoes for brunch? date night? Errands? Going to club or nice dinner?

Clothes, heels, accessories, and makeup are a wonderful way to express one’s style and personality. Clothes can convey confidence. I am always amazed (and delighted) at how versatile “girl clothes” are. There is a dress for literally every occasion I can think of.

When building or expanding a wardrobe, I would recommend reading an article I wrote for En Femme about the essentials.

This is probably a good time to mention that this is all strictly my opinion. What you fill your closet with, your lingerie drawer with, is 1000000% up to you. Create a wardrobe you want, wear clothes that you want to wear. There are no rules.

But since you asked, here’s what I would wear.

When it comes to heels, start with a pair of black heels and a pair of beige heels. These are the most practical and the most versatile as you can pair them with almost every outfit and are appropriate for almost any occasion. Black to dress up, beige to dress down.

Boots are essential for fall and winter. Something cute and strappy for summer. As you build your wardrobe you’ll start getting inspired as to which shoes would go best with the outfit. For example, this sparkly dress is beautiful, and yes, a pair of black heels would work, but I am happy I had a pair of gold heels to pair it with.

Accessorizing an outfit is not that different than cooking. Sampling the soup you are making might inspire you to add a spice (or whatever, I am not a chef). Picking out a dress will also inspire you to envision what heels you should wear with it.

As for choosing an outfit for an occasion, really, you can wear whatever you want to whatever you want, and what I would wear may be different than what you would choose. As I get older I get bolder, braver, more confident. I can’t blend in, so I fully embrace with standing out. Not to the point where I am wearing a gown to Target, but I love wearing bold patterns and bright colors, even if I am a little out of place. Not too many people wear heels to run errands, but this girl does.

Off the top of my head, here’s what I would wear to a few different events or places.

The Club

I am not really sure what I mean by the “The Club” but I suppose a crowded place with loud music and alcohol. 🙂 I think you can get away with an incredibly bold outfit at a club more than anywhere else. I would, and do, wear something more leathery or shiny, such as PVC.

Brunch

I love showing off my legs and I do so with any chance I get, but I would wear a dress or a skirt that touches my knees or longer. Probably something that isn’t sleeveless, too. Bright colors also seem perfect for brunch, too.

Dinner

Of course, this depends on the type of restaurant you go to, as well as the event. These are some of the outfits I have worn to dinner. This first dress is from a night out that included dinner and attending a play. The dress worked perfect for both.

The Office

Of course, I don’t work en femme, but I have a lot of outfits in my closet that would work just fine for the office. These two outfits are my best effort at a sexy CEO look. 🙂

Shopping

I dress for ME. I don’t dress for anyone else. What I wear when I hit the mall is a little overdressed compared to the other girls, I don’t hear a lot of other heels clicking on the floor besides my own.

I hope this helps! In looking over these photos I am seeing a wide variety of dresses and heels, but the really, wear what you want. 🙂

Love, Hannah

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