Amy Prokopowicz, 34, is a counselor who helps homeless women, but when she volunteers, she has gotten offers of free food. “I walked in and a lady said, ‘Aww, we’ll get you something,’ ”Amy said. “I said, ‘No, I’m here to help.’ I thought: Do I look bad?” Amy says she’s frugal and practical. “I would like to learn how to piece clothes together that are flattering. I will not become a fashionista, but would like to know basics about colors and styles.” I showed Amy how she can use two basic equations to build outfits with personality.

Practical but plain: Amy might wear this to meet clients as an addictions specialist, but it looks too casual. The shoes are sturdy and practical but not stylish. Amy shops based on low price first, not whether an item fits. She says she feels guilty spending money on her appearance when she sees so much need around her. She’ll look better and feel better if she spends her hard-earned dollars on clothes that fit and flatter her, because she’ll enjoy wearing them and will wear them more often.

Hair and makeup: Too much length weighs down Amy’s hair and makes it lie flat. Cutting off a few inches gives hair volume. Graduated layers frame Amy’s face and complement the shape. Foundation evens out her complexion, and shadow and liner highlight her blue eyes. A slick of lipstick brightens her smile.

Fresher Outfit 1: DARK JEANS + TOP + LONG SWEATER + ACCESSORIES = CASUAL. Stylish casual clothes are essential to dressing well. Create a long line with a dark jean (AG midrise cigarette jean) tucked into dark knee boots (Coclico). A boatneck top (James Perse) under a long cardigan (Organic by John Patrick) continues the sleek silhouette. Accessories (Stuart & Brown cashmere scarf, J.W. Hulme bag with brass hardware) are the touches of personality.

Fresher Outfit 2: DRESS + METALLIC HEELS + BRIGHT CLUTCH = DRESSY. When it’s time to get spiffy, a dress (Ecoskin) makes your life easy. Pick a flattering shape and neutral color so the dress is the backdrop for bold accessories. Add personality with heels (Anne Klein at Nordstrom Rack) that are updated with metallic shine. A shock of color comes from the red clutch bag (Clare Vivier). The antique brass necklace with Swarovski crystals shows individuality.

The reaction: The makeover was a bright spot for Amy during a difficult time. After two deaths in her family in three weeks and a relative’s illness took a toll, “I am a bit tired,” she said via email. “Otherwise, I just keep plugging along.” Still, she’s paying attention to her appearance. “I have purchased (a) red corduroy short blazer, longer stylish sweater and a new cardigan with a shirt to go under each one for a layered look,” she said. “Plus donated a few items that are blah and look frumpy.”