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1940’s Equestrian-Inspired Outfit of the Night

The other night I went out for dinner and a movie and wore this outfit. I was inspired by 1940’s pin-ups and classic English equestrian style. The cloche hat and tweed blazer were key, classic pieces that were fun to accessorize. I wore more modern straight-leg jeans to update the look. A red lip and winged eyeliner tied everything together.

Grey Cloche Hat: Gift

Cherry Detail Red Sweater: Modcloth

Elbow Patch Tweed Blazer: Ruche

Straight-leg Jeans: GAP

Black Riding Boots: Just Fab

Red Leather Gloves: Gift 


Hi Jen! Thank you so much for asking for my guidance! It is important to not show too much skin and to look classy at an occasion like a military ball. High-low hems are a great choice. They are feminine, modest, and delicate while still managing to be trendy and sexy. I know two of my suggestions are black and white, but keep in mind that these colors are always appropriate and that they dominate black-tie events like a military ball. All of these dresses would be appropriate and I’m sure your boyfriend would spend the evening proudly showing you off.

From left to right:
Sleeveless High-Low Dress w/ Belt, Forever 21, $22.80
Tahitian Waves Dress, Dress 911, $55.95
Island Apertif Dress, Modcloth, $52.99
Strapless Layered High-Low Dress, Forever 21, $32.80

Have a wonderful time at the ball!


Thanks for the great question, anon! Everybody has days when they just wish they could stay in their pajamas! On days where we want the comfort of lounging while still looking chic, we go for something like this. A classic comfy sweater and leggings looks fresh but feels like wearing sweats! Another essential item for fashionable comfort are flat-soled boots. They feel like wearing slippers or flats, but in my experience, look and feel way more stylish. Some more tips for amping up this look: an eye-catching scarf, a belt to cinch the waist, a colorful handbag, a hat, headband, or (if you have long hair) a braid.

Scarf: Women’s Embroidered Tassel Scarf in Red, Old Navy, $14.97
Sweater: Fireside Open-Knit Sweater in Cream, Forever 21, $22.80
Belt: Relic Wrapped Buckle Belt in Burgundy, Kohl’s, $18.00
Black boots: Kori Boot in Black, Delia’s, $29.90
Red boots: Route 66 Women’s Arizona Mid-Calf Western Boot in Red, Kmart, $14.99


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